AGREEMENT AND PLAN OF MERGER

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Exhibit 2.1

AGREEMENT AND PLAN OF MERGER

by and among

DEERFIELD PRIVATE DESIGN FUND, L.P.,
a Delaware limited partnership;

DEERFIELD PRIVATE DESIGN INTERNATIONAL, L.P.,
a British Virgin Islands limited partnership;

DEERFIELD SPECIAL SITUATIONS FUND, L.P.,
a Delaware limited partnership;

DEERFIELD SPECIAL SITUATIONS FUND INTERNATIONAL LIMITED,
a British Virgin Islands corporation;

NTMD PARENT ACQUISITION CORP.,
a Delaware corporation;

NTMD ACQUISITION CORP.,
a Delaware corporation; and

NITROMED, INC.,
a Delaware corporation

Dated as of January 27, 2009

Table of Contents

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AGREEMENT AND PLAN OF MERGER

        THIS AGREEMENT AND PLAN OF MERGER (this " Agreement ") is made and entered into as of January 27, 2009, by and among DEERFIELD PRIVATE DESIGN FUND, L.P. , a Delaware limited partnership (" DPDF ") DEERFIELD PRIVATE DESIGN INTERNATIONAL, L.P. , a British Virgin Islands limited partnership (" DPDI "), DEERFIELD SPECIAL SITUATIONS FUND, L.P. , a Delaware limited partnership (" DSSF "), DEERFIELD SPECIAL SITUATIONS FUND INTERNATIONAL LIMITED , a British Virgin Islands corporation (" DSSFI ") (collectively, " Deerfield "), NTMD PARENT ACQUISITION CORP. , a Delaware corporation and wholly owned subsidiary of Deerfield (" Parent "), NTMD ACQUISITION CORP. , a Delaware corporation and wholly owned subsidiary of Parent (" Merger Sub "); and NITROMED, INC. , a Delaware corporation (" NitroMed "). Certain capitalized terms used in this Agreement are defined in Exhibit A .

RECITALS

        A.    Deerfield and NitroMed intend to enter into a business combination transaction pursuant to which Merger Sub will merge with and into NitroMed (the " Merger ") in accordance with and subject to the terms of this Agreement and the DGCL.

        B.    The board of directors of NitroMed (i) has determined that the Merger is advisable and fair to, and in the best interests of, NitroMed and its stockholders, (ii) has approved this Agreement, the Merger and the other Contemplated Transactions and has deemed this Agreement advisable and (iii) has approved and determined to recommend the adoption of this Agreement to the stockholders of NitroMed.

        C.    The board of directors of Merger Sub (i) has determined that the Merger is advisable and fair to, and in the best interests of, Merger Sub and Parent as its sole stockholder, (ii) has approved this Agreement, the Merger and the other Contemplated Transactions and has deemed this Agreement advisable and (iii) has approved and determined to recommend the adoption of this Agreement to Parent as the sole stockholder of Merger Sub.

        D.    In order to induce Deerfield to enter into this Agreement and to cause the Merger to be consummated, NitroMed and the stockholders of NitroMed listed on Schedule 1 hereto are executing voting agreements and irrevocable proxies in favor of Deerfield concurrently with the execution and delivery of this Agreement in the form substantially attached hereto as Exhibit B (the " Stockholder Voting Agreements ").

        E.    In order to induce NitroMed to enter into this Agreement and to cause the Merger to be consummated, NitroMed, DSSF and DSSFI are executing a voting agreement and irrevocable proxies in favor of NitroMed concurrently with the execution and delivery of this Agreement in the form substantially attached hereto as Exhibit C (the " Deerfield Stockholder Voting Agreement ").

AGREEMENT

        The Parties to this Agreement, intending to be legally bound, agree as follows:

1.      DESCRIPTION OF TRANSACTION

        1.1     The Merger .    Upon the terms and subject to the conditions set forth in this Agreement, at the Effective Time (as defined in Section 1.3), Merger Sub shall be merged with and into NitroMed, the separate existence of Merger Sub shall cease, and NitroMed shall continue as the surviving corporation in the Merger (the " Surviving Corporation ").

        1.2     Effects of the Merger .    The Merger shall have the effects set forth in this Agreement and in the applicable provisions of the DGCL. Without limiting the generality of the foregoing, and subject thereto, at the Effective Time, all the property, rights, privileges, powers and franchises of NitroMed and Merger Sub shall vest in the Surviving Corporation, and all debts, liabilities and duties of NitroMed and Merger Sub shall become the debts, liabilities and duties of the Surviving Corporation.

        1.3     Closing; Effective Time .    Unless this Agreement is earlier terminated pursuant to the provisions of Section 9.1 of this Agreement, and subject to the satisfaction or waiver of the conditions set forth in Sections 6, 7 and 8 of this Agreement, the consummation of the Merger (the " Closing ") shall take place at the offices of Wilmer Cutler Pickering Hale and Dorr LLP, 60 State Street, Boston, Massachusetts 02109, as promptly as practicable (but in no event later than the fifth Business Day) following the satisfaction or waiver of the last to be satisfied or waived of the conditions set forth in Sections 6, 7 and 8 (other than those conditions that by their nature are to be satisfied at the Closing, but subject to the satisfaction or waiver of each of such conditions) or at such other time, date and place as Deerfield and NitroMed may mutually agree in writing. The date on which the Closing actually takes place is referred to as the " Closing Date ." At the Closing, the Parties hereto shall cause the Merger to be consummated by executing and filing with the Secretary of State of the State of Delaware a Certificate of Merger with respect to the Merger, satisfying the applicable requirements of the DGCL and in a form reasonably acceptable to Deerfield and NitroMed. The Merger shall become effective at the time of the filing of such Certificate of Merger with the Secretary of State of the State of Delaware or at such later time as may be agreed upon by Deerfield and NitroMed and specified in such Certificate of Merger (the time as of which the Merger becomes effective being referred to as the " Effective Time ").

        1.4     Certificate of Incorporation and Bylaws .    At the Effective Time:

        (a)   Subject to Section 5.4, the Certificate of Incorporation of the Surviving Corporation shall be amended and restated as of the Effective Time to be identical to the Certificate of Incorporation of Merger Sub as in effect immediately prior to the Effective Time, until thereafter amended as provided by the DGCL and such Certificate of Incorporation; and

        (b)   Subject to Section 5.4, Deerfield shall cause the By-laws of NitroMed as in effect immediately prior to the Effective Time to be amended and restated in their entirety so that, immediately following the Effective Time, they are identical to the By-laws of Merger Sub as in effect immediately prior to the Effective Time, except that all references to the name of Merger Sub therein shall be changed to refer to the name of NitroMed, and, as so amended and restated, such By-laws shall be the By-laws of the Surviving Corporation, until further amended in accordance with the DGCL.

        1.5     Conversion of NitroMed Shares .    

        (a)   At the Effective Time, by virtue of the Merger and without any further action on the part of Deerfield, NitroMed or any stockholder of NitroMed:

          (i)  any shares of NitroMed Common Stock held as treasury stock or held or owned by Merger Sub immediately prior to the Effective Time shall be canceled and shall cease to exist, and no consideration shall be delivered in exchange therefor;

         (ii)  each share of NitroMed Common Stock outstanding immediately prior to the Effective Time (excluding shares to be canceled pursuant to Section 1.6(a)(i) and excluding Dissenting Shares) shall be converted solely into the right to receive the Merger Consideration, without any interest thereon.

        (b)   Each share of Common Stock, $0.01 par value per share, of Merger Sub issued and outstanding immediately prior to the Effective Time shall be converted into and exchanged for one validly issued, fully paid and nonassessable share of Common Stock, $0.01 par value per share, of the Surviving Corporation. Each stock certificate of Merger Sub evidencing ownership of any such shares shall, as of the Effective Time, evidence ownership of such shares of Common Stock of the Surviving Corporation.

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        1.6     Calculation of Net Cash and Inventory .    

        (a)   No later than the date of mailing of the Proxy Statement to the holders of NitroMed Common Stock, NitroMed and Deerfield shall agree upon a measurement date (the " Measurement Date ") which shall be a date anticipated to be ten Business Days prior to the date of the NitroMed Stockholders' Meeting. No later than the close of business five Business Days after the Measurement Date, NitroMed shall deliver by email or facsimile transmission to Deerfield a schedule (a " Net Cash Schedule "), setting forth, in reasonable detail, the Net Cash as of the Measurement Date. NitroMed shall promptly furnish to Deerfield the work papers and back-up materials used in preparing the Net Cash Schedule. Without the prior written consent of Deerfield, which consent shall not be unreasonably withheld, from the Measurement Date until the Closing Date, NitroMed shall not incur any expenses not set forth on the Net Cash Schedule individually in excess of $25,000 or in the aggregate in excess of $50,000 and other than legal, accounting and other expenses incurred in connection with the Merger and the other Contemplated Transactions and other matters contemplated by this Agreement.

        (b)   Within five Business Days after NitroMed delivers the Net Cash Schedule (the " Lapse Date "), Deerfield shall have the right to dispute any part of such Net Cash Schedule by delivering by email or facsimile a written notice to that effect to NitroMed (a " Dispute Notice "). Any Dispute Notice shall identify in reasonable detail the nature of any proposed revisions to the Net Cash Schedule and Net Cash as of the Measurement Date.

        (c)   If on or prior to the Lapse Date, (i) Deerfield notifies NitroMed that it has no objections to the applicable Net Cash Schedule or (ii) Deerfield fails to deliver a Dispute Notice as provided above, then the Net Cash as set forth in the Net Cash Schedule shall be deemed to have been finally determined for purposes of this Agreement and to represent the "Final Net Cash" for purposes of the definition of Merger Consideration in Exhibit A hereto.

        (d)   If Deerfield delivers a Dispute Notice on or prior to the Lapse Date, then Representatives of NitroMed and Deerfield shall meet within two Business Days and attempt in good faith to resolve the disputed item(s), to negotiate an agreed-upon determination of Net Cash as of the Measurement Date, and to exchange in writing any proposed change from the amount of Net Cash as included by a Party its respective Net Cash Schedule or Dispute Notice. If as a result of such negotiation, NitroMed and Deerfield agree upon the amount of Net Cash, such agreed-upon Net Cash amount shall be deemed to have been finally determined for purposes of this Agreement and to represent the Final Net Cash for purposes of the definition of Merger Consideration in Exhibit A hereto.

        (e)   If Representatives of NitroMed and Deerfield are unable to negotiate an agreed-upon determination of Net Cash within two Business Days of the delivery of a Dispute Notice, NitroMed and Deerfield shall jointly engage the Neutral Accountant to review the Net Cash Schedule, Dispute Notice and such other materials as NitroMed and Deerfield supply within five Business Days of the delivery of a Dispute Notice and shall determine as soon as practical, and anticipated to be within five Business Days, the Net Cash at the Measurement Date, which determination will be binding and not subject to any appeal. The amount of Net Cash included in the latest written proposal of Net Cash delivered by a one Party to the other Party pursuant to Section 1.6(d) that differs in aggregate the least from the binding determination made by the Neutral Accountant shall be deemed to represent the Final Net Cash for purposes of the definition of Merger Consideration in Exhibit A hereto and to be finally determined for purposes of this Agreement. The expenses charged by the Neutral Accountant to make such determination (the " Accountant's Expenses ") shall be identified at the time of such determination and borne by the Party whose latest written proposal of Net Cash delivered by it to the other Party pursuant to Section 1.6(d) differs in aggregate the most from the binding determination made by the Neutral

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Accountant hereunder, and if borne by NitroMed shall be included in the determination of Merger Consideration pursuant to the definition thereof in Exhibit A hereto.

        (f)    NitroMed and Deerfield shall jointly engage the Neutral Accountant to make a physical count and a determination (in accordance with the definition of "Inventory" included in Exhibit A hereto) of the Inventory on the Measurement Date. Deerfield and NitroMed shall each be permitted to have one or more representatives present during such physical count. With respect to any location at which inventory is maintained for which (i) the third party service provider that manages such location has received an unqualified opinion on a Report on Controls Placed in Operation and Tests of Operating Effectiveness (SAS 70 Type II) or (ii) the net book value of the Inventory at such location is less than $100,000, Deerfield and NitroMed will rely on the physical count made by the third party service provider that manages such location, provided that such physical count is made within five Business Days of the Measurement Date. Deerfield and NitroMed will rely upon the physical count made by any such third party service provider to calculate the portion of the Inventory as of the Measurement Date at the locations referenced in the preceding sentence. The Neutral Accountant shall promptly deliver to Deerfield and NitroMed a report (the " Physical Count Inventory Report ") reflecting its determinations regarding the Inventory as of the Measurement Date and setting forth the specific adjustments to the Inventory amount if any. The Inventory as reflected on the Physical Inventory Report, as adjusted by additions to Inventory and sales of Inventory occurring after the Measurement Date as reflected on NitroMed's books and records, shall be the basis for the determination of the Inventory for the purposes of Section 5.10. The fees and expenses of the Neutral Accountant with respect to the engagement described in this Section 1.6(f) are referred to herein as the " Inventory Expenses ."

        1.7     Closing of NitroMed's Transfer Books .    At the Effective Time: (a) all shares of NitroMed Common Stock outstanding immediately prior to the Effective Time shall automatically be canceled and shall cease to exist, and all holders of certificates representing shares of NitroMed Common Stock that were outstanding immediately prior to the Effective Time shall cease to have any rights as stockholders of NitroMed except as otherwise provided herein; and (b) the stock transfer books of NitroMed shall be closed with respect to all shares of NitroMed Common Stock outstanding immediately prior to the Effective Time. No further transfer of any such shares of NitroMed Common Stock shall be made on such stock transfer books after the Effective Time. If, after the Effective Time, a valid certificate previously representing any shares of NitroMed Common Stock outstanding immediately prior to the Effective Time (a " Stock Certificate ") is presented to the Paying Agent (as defined in Section 1.8) or to the Surviving Corporation, such Stock Certificate shall be canceled and shall be exchanged as provided in Section 1.8.

        1.8     Surrender of Certificates .    

        (a)   On or prior to the Closing Date, NitroMed and Deerfield shall agree upon and select a reputable bank, transfer agent or trust company to act as paying agent in the Merger (the " Paying Agent "). At the Effective Time, Deerfield shall deposit with the Paying Agent an amount equal to the aggregate Merger Consideration less the Closing Cash Distribution Amount (collectively with the Closing Cash Distribution Amount, the " Payment Fund "). Within one Business Day after the Effective Time, Deerfield shall cause the Surviving Corporation to remit to the Paying Agent an amount equal to the Closing Cash Distribution Amount.

        (b)   Promptly after the Effective Time, but in no event more than 5 Business Days after the Effective Time, the Parties shall cause the Paying Agent to mail to the Persons who were record holders of Stock Certificates immediately prior to the Effective Time: (i) a letter of transmittal in customary form and containing such provisions as Deerfield may reasonably specify (including a provision confirming that delivery of Stock Certificates shall be effected, and risk of loss and title to Stock Certificates shall pass, only upon delivery of such Stock Certificates to the Paying Agent);

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and (ii) instructions for use in effecting the surrender of Stock Certificates in exchange for the Merger Consideration. Upon surrender of a Stock Certificate to the Paying Agent for exchange, together with a duly executed letter of transmittal and such other documents as may be reasonably required by the Paying Agent or Deerfield: (A) the holder of such Stock Certificate shall be entitled to receive in exchange therefor the Merger Consideration that such holder has the right to receive pursuant to the provisions of Section 1.5(a)(ii); and (B) the Stock Certificate so surrendered shall be canceled. In the event of a transfer of ownership of NitroMed Common Stock which is not registered in the transfer records of NitroMed, the Merger Consideration may be paid to a person other than the person in whose name the applicable Stock Certificate so surrendered is registered, if such Stock Certificate is presented to the Paying Agent, accompanied by all documents required to evidence and effect such transfer and by evidence that any applicable stock transfer taxes have been paid, along with an applicable affidavit with respect to such Stock Certificate and such bond indemnifying Deerfield against any claims suffered by Deerfield related to such Stock Certificate or any Merger Consideration paid in exchange therefor as Deerfield may reasonably request. Until surrendered as contemplated by this Section 1.8(b), each Stock Certificate shall be deemed, from and after the Effective Time, to represent only the right to receive the Merger Consideration as contemplated by Section 1.5(a)(ii). If any Stock Certificate shall have been lost, stolen or destroyed, Deerfield may, in its discretion and as a condition precedent to the delivery of any Merger Consideration with respect to the shares of NitroMed Common Stock previously represented by such Stock Certificate, require the owner of such lost, stolen or destroyed Stock Certificate to provide an applicable affidavit with respect to such Stock Certificate and post a bond indemnifying Deerfield against any claim suffered by Deerfield related to the lost, stolen or destroyed Stock Certificate or any Merger Consideration paid in exchange therefor as Deerfield may reasonably request.

        (c)   Any portion of the Payment Fund that remains undistributed to holders of Stock Certificates as of the date 180 days after the Closing Date shall be delivered or made available to Deerfield upon demand, and any holders of Stock Certificates who have not theretofore surrendered their Stock Certificates in accordance with this Section 1.8 shall thereafter look only to Deerfield for satisfaction of their claims for Merger Consideration.

        (d)   Each of the Paying Agent and Deerfield shall be entitled to deduct and withhold from the Merger Consideration payable pursuant to this Agreement to any holder of any Stock Certificate such amounts as Deerfield determines in good faith are required to be deducted or withheld from such consideration under the Code or any provision of state, local or foreign tax law or under any other applicable Legal Requirement. To the extent such amounts are so deducted or withheld, such amounts shall be treated for all purposes under this Agreement as having been paid to the Person to whom such amounts would otherwise have been paid.

        (e)   No party to this Agreement shall be liable to any holder of any Stock Certificate or to any other Person with respect to any shares of NitroMed Common Stock (or dividends or distributions with respect thereto), or for any cash amounts, delivered to any public official pursuant to any applicable abandoned property law, escheat law or similar Legal Requirement.

        1.9     Appraisal Rights .    

        (a)   Notwithstanding any provision of this Agreement to the contrary, shares of NitroMed Common Stock that are outstanding immediately prior to the Effective Time and which are held by stockholders who have exercised and perfected appraisal rights for such shares of NitroMed Common Stock in accordance with the DGCL (collectively, the " Dissenting Shares ") shall not be converted into or represent the right to receive the Merger Consideration described in Section 1.5(a)(ii) attributable to such Dissenting Shares. Such stockholders shall be entitled to receive payment of the appraised value of such shares of NitroMed Common Stock held by them

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in accordance with the DGCL, unless and until such stockholders fail to perfect or effectively withdraw or otherwise lose their appraisal rights under the DGCL. All Dissenting Shares held by stockholders who shall have failed to perfect or who effectively shall have withdrawn or lost their right to appraisal of such shares of NitroMed Common Stock under the DGCL shall thereupon be deemed to be converted into and to have become exchangeable for, as of the Effective Time, the right to receive the Merger Consideration attributable to such Dissenting Shares upon their surrender in the manner provided in Section 1.8.

        (b)   NitroMed shall give Deerfield (i) prompt written notice of any demands by dissenting stockholders received by NitroMed, withdrawals of such demands and any other instruments served on NitroMed and any material correspondence received by NitroMed in connection with such demands and (ii) the opportunity to direct all negotiations and proceedings with respect to demands for appraisal under the DGCL. NitroMed shall not, except with the prior written consent of Deerfield, voluntarily make any payment with respect to any demands for appraisals of Dissenting Shares, offer to settle or settle any such demands or approve any withdrawal of any such demands.

        1.10     Further Action .    If, at any time after the Effective Time, any further action is determined by the Surviving Corporation to be necessary or desirable to carry out the purposes of this Agreement or to vest the Surviving Corporation with full right, title and possession of and to all rights and property of NitroMed, then the officers and directors of the Surviving Corporation shall be fully authorized, and shall use their commercially reasonable efforts (in the name of NitroMed and otherwise) to take such action.

        1.11     NitroMed Stock Options .    Each NitroMed Option outstanding immediately prior to the Effective Time shall be accelerated and shall be converted automatically into the right to receive an amount, if positive, equal to (i) the Merger Consideration minus (ii) the exercise price payable in respect of each share of NitroMed Common Stock issuable under such NitroMed Option.

        1.12     Agreed Tax Treatment .    For federal, state and local income Tax purposes, the Parties agree to treat the Contemplated Transactions as follows: pursuant to an integrated plan, (a) the redemption by NitroMed, in exchange for the Closing Cash Distribution Amount, of a number of shares of NitroMed Common Stock equal to the total number of such outstanding shares of NitroMed Common Stock at the Effective Time multiplied by a fraction the numerator of which is the Closing Cash Distribution Amount and the denominator of which is the aggregate Merger Consideration and (b) the purchase by Deerfield of the remaining outstanding shares of NitroMed Common Stock in exchange for the balance of the aggregate Merger Consideration.

        1.13     Withholding .    Deerfield shall be entitled to deduct, withhold and pay over to the applicable Governmental Body from the consideration otherwise payable pursuant to this Agreement to any recipient of a payment hereunder such minimum amounts as it is required to deduct and withhold with respect to the making of such payment under the Code, or any provision of state, local or foreign tax law. To the extent that amounts are so withheld by Deerfield, such withheld amounts shall be treated for all purposes of this Agreement as having been paid to the applicable recipient in respect of which such deduction and withholding was made by Deerfield, and Deerfield covenants that such withholding shall be paid to the applicable Governmental Body when such amount is due.

2.      REPRESENTATIONS AND WARRANTIES OF NITROMED

        NitroMed represents and warrants to Deerfield as follows, except as set forth in the written disclosure schedule delivered or made available by NitroMed to Deerfield (the " Disclosure Schedule "). The Disclosure Schedule shall be arranged in sections and subsections corresponding to the numbered and lettered sections and subsections contained in this Section 2. The disclosure in any section or subsection of the Disclosure Schedule shall qualify other sections and subsections in this Section 2 only

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to the extent that disclosure in one subsection of the Disclosure Schedule is specifically referred to in another subsection of the Disclosure Schedule by appropriate cross-reference and except to the extent that the relevance of a disclosure in one subsection of the Disclosure Schedule to another subsection of the Disclosure Schedule is reasonably apparent.

        2.1     Due Organization; Subsidiaries; Etc .    

        (a)   NitroMed is a corporation duly organized, validly existing and in good standing under the laws of the State of Delaware, with the corporate power and authority to conduct its business in the manner in which its business is currently being conducted and to own and use its assets in the manner in which its assets are currently owned and used.

        (b)   NitroMed has not conducted any business under or otherwise used, for any purpose or in any jurisdiction, any fictitious name, assumed name, trade name or other name, other than the name "NitroMed, Inc."

        (c)   NitroMed is not and has not been required to be qualified, authorized, registered or licensed to do business as a foreign corporation in any jurisdiction, except where the failure to be so qualified, authorized, registered or licensed, individually or in the aggregate, has not had, and would not reasonably be expected to have, a NitroMed Material Adverse Effect. NitroMed and its Subsidiaries are each in good standing as a foreign corporation in each of the jurisdictions identified in Part 2.1(c) of the Disclosure Schedule.

        (d)   Part 2.1(d) of the Disclosure Schedule accurately sets forth (i) the names of the members of the board of directors of NitroMed, (ii) the names of the members of each committee of the board of directors of NitroMed and (iii) the names and titles of NitroMed's officers.

        (e)   NitroMed has no Subsidiaries except for the Entities identified in Part 2.1(e) of the Disclosure Schedule. Neither NitroMed nor any NitroMed Subsidiary has agreed or is obligated to make any future investment in or capital contribution to any Entity. Except as identified in Part 2.1(e) of the Disclosure Schedule, neither NitroMed nor any NitroMed Subsidiary has guaranteed or is responsible or liable for any obligation of any of the Entities in which it owns or has owned any equity or other financial interest. Except as set forth in Part 2.1(e) of the Disclosure Schedule, NitroMed does not own any controlling interest in any Entity, and NitroMed has never owned, beneficially or otherwise, any shares or other securities of, or any direct or indirect equity or other financial interest in, any Entity.

        2.2     Certificate of Incorporation and Bylaws; Records .    NitroMed has delivered or made available to Deerfield copies of: (a) NitroMed's certificate of incorporation and bylaws, including all amendments thereto; (b) the stock records of NitroMed; and (c) the minutes and other records of the meetings and other proceedings (including any actions taken by written consent or otherwise without a meeting) of the stockholders of NitroMed, the board of directors of NitroMed and all committees of the board of directors of NitroMed (the " NitroMed Constituent Documents "). There have been no formal meetings or other proceedings of the stockholders of NitroMed, the board of directors of NitroMed or any committee of the board of directors of NitroMed that are not fully reflected in the minutes and other records delivered or made available to Deerfield pursuant to clause (c) above. There has not been any violation in any material respect of the NitroMed Constituent Documents, and NitroMed has not taken any action that is inconsistent in any material respect with the NitroMed Constituent Documents. The books of account, stock records, minute books and other records of NitroMed are accurate, up to date and complete in all material respects.

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        2.3     Capitalization, Etc .    

        (a)   As of the date hereof, the authorized capital stock of NitroMed consists of: 65,000,000 shares of NitroMed Common Stock and 5,000,000 shares of Preferred Stock, par value $.01 per share. As of the date hereof, 46,075,133 shares of NitroMed Common Stock have been issued and are outstanding, and no shares of NitroMed Preferred Stock have been issued and are outstanding. All outstanding shares of NitroMed Common Stock have been duly authorized and validly issued, and are fully paid and non assessable. All outstanding shares of NitroMed Common Stock have been issued and granted in compliance with (i) all applicable federal and state securities laws and other applicable Legal Requirements, and (ii) all requirements set forth in NitroMed Constituent Documents and applicable Contracts. NitroMed has no authorized shares other than as set forth in this Section 2.3(a) and there are no issued and outstanding shares of NitroMed's capital stock other than the shares of NitroMed Common Stock as set forth in this Section 2.3(a).

        (b)   As of the date hereof, NitroMed has reserved 2,288,200 shares of NitroMed Common Stock for issuance under its Restated 1993 Equity Incentive Plan, of which options to purchase 242,500 shares of NitroMed Common Stock are outstanding as of such date; 9,019,679 shares of NitroMed Common Stock for issuance under its Amended and Restated 2003 Stock Incentive Plan (together with the Restated 1993 Equity Incentive Plan, the " NitroMed Option Plans "), of which options to purchase 2,632,824 shares of NitroMed Common Stock are outstanding as of such date; and 675,000 shares of NitroMed Common Stock for issuance under its 2003 Employee Stock Purchase Plan, as amended, of which 173,733 shares of NitroMed Common Stock are outstanding as of such date. In addition, as of the date hereof, an aggregate of 4,210,213 shares of NitroMed Common Stock are available for future grant under the NitroMed Option Plans. Except as set forth in this Agreement and the Contemplated Transactions, there is no: (i) outstanding subscription, option, call, warrant or right (whether or not currently exercisable) to acquire any shares of the capital stock or other securities of NitroMed; (ii) outstanding security, instrument or obligation that is or may become convertible into or exchangeable for any shares of capital stock or other securities of NitroMed; (iii) Contract under which NitroMed is or may become obligated to sell or otherwise issue any shares of its capital stock or any other securities of NitroMed; or (iv) condition or circumstance that would give rise to or provide a basis for the assertion of a claim by any Person to the effect that such Person is entitled to acquire or receive any shares of capital stock or other securities of NitroMed. NitroMed has not issued any debt securities which grant the holder thereof any right to vote on, or veto, any action of NitroMed.

        (c)   All outstanding NitroMed Options have been issued and granted in compliance with (i) all applicable securities laws and other applicable Legal Requirements, and (ii) all requirements set forth in NitroMed Constituent Documents and applicable Contracts. Part 2.3(c) of the Disclosure Schedule sets forth a complete and accurate list, as of the date of this Agreement, of all outstanding NitroMed Options, indicating with respect to each such NitroMed Option the name of the holder thereof, the number of shares of NitroMed Common Stock subject to such NitroMed Option and the exercise price thereof.

        2.4     SEC Filings; Financial Statements .    

        (a)   NitroMed has made all filings with the SEC required under the applicable requirements of the Securities Act and the Exchange Act. NitroMed has delivered or made available to Deerfield accurate and complete copies (excluding copies of exhibits) of each report, schedule, registration statement and definitive proxy statement filed by NitroMed with the SEC on or after January 1, 2007 and prior to the date of this Agreement (the " NitroMed SEC Documents "). NitroMed has resolved with the staff of the SEC any comments it may have received since January 1, 2007 and prior to the date of this Agreement in comment letters to NitroMed from the staff of the SEC or, to the extent such comments are unresolved, has disclosed such unresolved

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comments in the NitroMed SEC Documents. All NitroMed SEC Documents (x) were filed on a timely basis, (y) at the time filed (or, if amended or superseded by a later filing prior to the date of this Agreement, than on the date of such later filing), were prepared in compliance in all material respects with the applicable requirements of the Securities Act or the Exchange Act, as the case may be, and the rules and regulations of the SEC thereunder applicable to such NitroMed SEC Documents, and (z) did not at the time they were filed contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary in order to make the statements therein, in light of the circumstances in which they were made, not misleading. Each of the principal executive officer of NitroMed and the principal financial officer of NitroMed (or each former principal executive officer of NitroMed and each former principal financial officer of NitroMed, as applicable) has made all certifications required by Rule 13a-14 or 15d-14 under the Exchange Act or Sections 302 and 906 of SOX and the rules and regulations of the SEC promulgated thereunder with respect to the NitroMed SEC Documents. For purposes of the preceding sentence, "principal executive officer" and "principal financial officer" shall have the meanings given to such terms in the Sarbanes-Oxley Act. The certifications and statements required by (A) Rule 13a-14 under the Exchange Act and (B) 18 U.S.C. §1350 (Section 906 of the Sarbanes-Oxley Act) relating to the NitroMed SEC Documents are accurate and complete and comply as to form and content with all applicable legal requirements. The consolidated financial statements contained in the NitroMed SEC Documents (including, in each case, any related notes thereto): (i) complied as to form in all material respects with the published rules and regulations of the SEC applicable thereto; (ii) were prepared in accordance with generally accepted accounting principles (" GAAP ") applied on a consistent basis throughout the periods covered, except as may be indicated in the notes to such consolidated financial statements and except that the unaudited interim consolidated financial statements contained in the NitroMed SEC Documents do not contain footnotes as permitted by Form 10-Q of the Exchange Act; and (iii) fairly present the consolidated financial position of NitroMed as of the respective dates thereof and the consolidated results of operations and cash flows of NitroMed for the periods covered thereby, except that the unaudited interim consolidated financial statements contained in the NitroMed SEC Documents were or are subject to normal year-end audit adjustments.

        (b)   Ernst & Young LLP, NitroMed's auditors are, and have been at all times during their engagement by NitroMed (i) "independent" with respect to NitroMed within the meaning of Regulation S-X and (ii) in compliance with subsections (g) through (l) of Section 10A of the Exchange Act (to the extent applicable) and the related rules of the SEC and the public company accounting oversight board, in each case as such subsections and rules apply to Ernst & Young LLP's engagement with NitroMed.

        2.5     Absence of Changes .    Since September 30, 2008:

        (a)   there has not been any NitroMed Material Adverse Effect, and no event has occurred that will, or would reasonably be expected to, result in a NitroMed Material Adverse Effect;

        (b)   there has not been any material loss, damage or destruction to, or any material interruption in the use of, any of the assets of NitroMed or any NitroMed Subsidiary (whether or not covered by insurance);

        (c)   NitroMed has not declared, accrued, set aside or paid any dividend or made any other distribution in respect of any shares of its capital stock, and has not repurchased, redeemed or otherwise reacquired any shares of its capital stock or other securities;

        (d)   NitroMed has not sold, issued, granted or authorized the issuance of (i) any capital stock or other securities of NitroMed; (ii) any option, call or right to acquire any capital stock or any other security of NitroMed; (iii) any instrument convertible into or exchangeable for any capital

9

 

stock or other security of NitroMed; or (iv) reserved for issuance any additional grants or shares under the NitroMed Option Plans or the 2003 Employee Stock Purchase Plan;

        (e)   there has been no amendment to the certificate of incorporation or bylaws of NitroMed or any NitroMed Subsidiary and NitroMed has not effected or been a party to any Acquisition Transaction, recapitalization, reclassification of shares, stock split, reverse stock split or similar transaction;

        (f)    NitroMed has not formed any NitroMed Subsidiary or acquired any equity interest or other interest in any other Entity;

        (g)   neither NitroMed nor any NitroMed Subsidiary has made any capital expenditure which, when added to all other capital expenditures made on behalf of NitroMed or any NitroMed Subsidiary exceeds $100,000;

        (h)   neither NitroMed nor any NitroMed Subsidiary has (i) entered into or permitted any of the assets owned or used by it to become bound by any Contract that contemplates or involves (A) the payment or delivery of cash or other consideration in an amount or having a value in excess of $100,000 in the aggregate, or (B) the purchase or sale of any product, or performance of services by or to NitroMed or any NitroMed Subsidiary having a value in excess of $100,000 in the aggregate, or (ii) waived any right or remedy under any Contract other than in the Ordinary Course of Business, or amended or prematurely terminated any Contract other than in the Ordinary Course of Business;

        (i)    neither NitroMed nor any NitroMed Subsidiary has (i) acquired, leased or licensed any right or other asset from any other Person, (ii) sold or otherwise disposed of, or leased or licensed, any right or other asset to any other Person, or (iii) waived or relinquished any right, except for immaterial rights or immaterial assets acquired, leased, licensed or disposed of in the Ordinary Course of Business;

        (j)    neither NitroMed nor any NitroMed Subsidiary has written off as uncollectible, or established any extraordinary reserve (as such terms are used in accordance with GAAP) with respect to, any account receivable or other indebtedness;

        (k)   neither NitroMed nor any NitroMed Subsidiary has made any pledge of any of its assets or otherwise permitted any of its assets to become subject to any material Encumbrance, except for pledges of immaterial assets made in the Ordinary Course of Business;

        (l)    neither NitroMed nor any NitroMed Subsidiary has (i) lent money to any Person (other than pursuant to routine travel advances made to employees in the Ordinary Course of Business), or (ii) incurred or guaranteed any indebtedness for borrowed money in the aggregate in excess of $50,000 or (iii) issued or sold any debt securities or options, warrants, calls or similar rights to acquire any debt securities of NitroMed or any NitroMed Subsidiary;

        (m)  neither NitroMed nor any NitroMed Subsidiary has (i) established or adopted any employee benefit plan, (ii) paid any bonus or made any profit sharing, incentive compensation or similar payment to, or increased the amount of the wages, salary, commissions, fringe benefits or other compensation or remuneration payable to, any of its directors, officers or employees with an annual base salary in excess of $200,000, or (iii) hired any new employee having an aggregate salary in excess of $100,000;

        (n)   neither NitroMed nor any NitroMed Subsidiary has changed any of its personnel policies or other business policies, or any of its methods of accounting or accounting practices in any material respect;

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        (o)   neither NitroMed nor any NitroMed Subsidiary has (i) made any material Tax election, or adopted or changed any material accounting method in respect of Taxes, (ii) entered into any closing agreement, settled or compromised any claim or assessment in respect of Taxes other than with respect to a claim or assessment which existed on the date hereof and in an amount not greater than the liability or reserve that has been recorded with respect thereto in the NitroMed Balance Sheet or any other balance sheet referenced in Section 2.6(a), or (iii) consented to any extension or waiver of any limitation period with respect to any claim or assessment for Taxes;

        (p)   neither NitroMed nor any NitroMed Subsidiary has threatened, commenced or settled any Legal Proceeding;

        (q)   neither NitroMed nor any NitroMed Subsidiary has entered into any transaction or taken any other action outside the Ordinary Course of Business, other than entering into this Agreement and the Contemplated Transactions;

        (r)   neither NitroMed nor any NitroMed Subsidiary has paid, discharged or satisfied any claim, liability or obligation (absolute, accrued, asserted or unasserted, contingent or otherwise) other than the payment, discharge or satisfaction of non-material amounts in the Ordinary Course of Business or as required by any NitroMed or NitroMed Subsidiary Contract or Legal Requirement; and

        (s)   neither NitroMed nor any NitroMed Subsidiary has agreed to take, or committed to take, any of the actions referred to in clauses "(c)" through "(r)" above.

        2.6     Liabilities; Fees, Costs and Expenses .    

        (a)   Neither NitroMed nor any NitroMed Subsidiary has any accrued, contingent or other liabilities of any nature, either matured or unmatured (whether or not required to be reflected in financial statements in accordance with GAAP, and whether due or to become due), except for: (i) liabilities identified in NitroMed's balance sheet included in its Form 10-K for the year ended December 31, 2007 (the " NitroMed Balance Sheet ") or any subsequent interim or full-year balance sheet filed by NitroMed with the SEC subsequent to December 31, 2007, or otherwise described in NitroMed's Form 10-K for the year ended December 31, 2007; (ii) liabilities that have been incurred since December 31, 2007 (or the date of any subsequent interim or full-year balance sheet filed by NitroMed with the SEC subsequent to December 31, 2007) in the Ordinary Course of Business; (iii) liabilities which have arisen since the date of the NitroMed Balance Sheet in the Ordinary Course of Business and (iv) contractual and other liabilities incurred in the Ordinary Course of Business which are not required by GAAP to be reflected on a balance sheet.

        (b)   The total amount of all fees, costs and expenses (including any attorney's, accountant's, financial advisor's or finder's fees) incurred by or for the benefit of NitroMed or any NitroMed Subsidiary in connection with (i) any due diligence conducted by NitroMed with respect to the Merger, (ii) the negotiation, preparation and review of this Agreement (including the Disclosure Schedule) and all agreements contemplated by this Agreement and opinions delivered or to be delivered in connection with the Contemplated Transactions, (iii) the preparation and submission of any filing or notice required to be made or given in connection with any of the Contemplated Transactions, (iv) the obtaining of any Consent required to be obtained in connection with any Contemplated Transactions hereby, and (v) otherwise in connection with the Merger and the Contemplated Transactions, will, in the good faith estimate of NitroMed reasonably exercised, aggregate approximately the amount set forth in Part 2.6(b) of the Disclosure Schedule.

        2.7     Compliance with Legal Requirements .    NitroMed and each NitroMed Subsidiary are, and since January 1, 2005 have been, in compliance in all material respects with all applicable Legal Requirements. NitroMed has not received, since January 1, 2005, any written notice or other communication from any Governmental Body or any other Person regarding (a) any actual, alleged,

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possible or potential material violation of, or material failure to comply with, any Legal Requirement, or (b) any actual, alleged, possible or potential material obligation on the part of NitroMed or the applicable NitroMed Subsidiary to undertake, or to bear all, or any portion of the cost of, any material cleanup or any material remedial, corrective or responsive action of any nature. NitroMed has delivered or made available to Deerfield an accurate and complete copy of each report, study, survey or other document to which NitroMed or any NitroMed Subsidiary has access that addresses or otherwise relates to the compliance or non-compliance of NitroMed and any NitroMed Subsidiary with, or the applicability to NitroMed or any NitroMed Subsidiary of, any Legal Requirement. To the Knowledge of NitroMed, no Governmental Body has proposed or is considering any Legal Requirement that, if adopted or otherwise put into effect, (i) will, or would reasonably be expected to, result in a NitroMed Material Adverse Effect, (ii) may have a material adverse effect on NitroMed's ability to comply with or perform any covenant or obligation under this Agreement or the Related Agreements, or (iii) may have the materially effect of preventing, delaying, making illegal or otherwise interfering with the Merger or any of the Contemplated Transactions.

        2.8     Governmental Authorizations .    Part 2.8 of the Disclosure Schedule identifies each Governmental Authorization held by NitroMed, and NitroMed has delivered or made available to Deerfield accurate and complete copies of all Governmental Authorizations identified in Part 2.8 of the Disclosure Schedule. The Governmental Authorizations identified in Part 2.8 of the Disclosure Schedule are valid and in full force and effect, and collectively constitute all material Governmental Authorizations necessary to enable NitroMed to conduct its business in the manner in which its business is currently being conducted and is proposed to be conducted. NitroMed is in compliance in all material respects with the terms and requirements of the respective Governmental Authorizations identified in Part 2.8 of the Disclosure Schedule. NitroMed has not since January 1, 2007 received any written notice or other written communication from any Governmental Body regarding (a) any actual or possible material violation of or material failure to comply with any term or requirement of any Governmental Authorization, or (b) any actual or possible revocation, withdrawal, suspension, cancellation, termination or material modification of any Governmental Authorization.

        2.9     Equipment; Leasehold .    

        (a)   All items of equipment and other tangible assets owned by or leased to NitroMed or any NitroMed Subsidiary (i) are adequate for the uses to which they are being put and (ii) are adequate for the conduct of NitroMed's business in the manner in which such business is currently being conducted and as it is currently proposed to be conducted.

        (b)   Neither NitroMed nor any NitroMed Subsidiary owns any real property or any interest in real property, except for the leasehold interest created under the real property leases identified in Part 2.9(b) of the Disclosure Schedule.

        2.10     Intellectual Property .    

        (a)   Part 2.10(a) of the Disclosure Schedule accurately identifies and describes each proprietary product or service that has been developed or has been commercially sold by NitroMed or a NitroMed Subsidiary within the last five (5) years and any product or service that is currently under development or that is currently commercially sold by NitroMed or a NitroMed Subsidiary.

        (b)   Part 2.10(b) of the Disclosure Schedule accurately identifies (i) each item of NitroMed Registered IP in which NitroMed or a NitroMed Subsidiary has or purports to have an ownership interest of any nature; (ii) the jurisdiction in which such item of NitroMed Registered IP has been registered or filed and the applicable registration or serial number; and (iii) any other Person that, to the Knowledge of NitroMed, may have an ownership interest in such item of NitroMed Registered IP and the nature of such ownership interest. NitroMed has delivered or made

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available to Deerfield complete and accurate copies of all applications and correspondence associated with the obtaining and maintenance of NitroMed IP Rights to or from a Governmental Body related to each such item of NitroMed Registered IP.

        (c)   Part 2.10(c) of the Disclosure Schedule accurately identifies (i) all NitroMed IP Rights licensed to NitroMed or a NitroMed Subsidiary (other than any non-customized software that (A) is so licensed solely in executable or object code form pursuant to a non-exclusive, internal use software license and (B) is not incorporated into, or used directly in the development, manufacturing, or distribution of, any of NitroMed's products or services); (ii) the corresponding NitroMed Contracts pursuant to which such NitroMed IP Rights are licensed to NitroMed or a NitroMed Subsidiary; and (iii) whether the license or licenses granted to NitroMed or a NitroMed Subsidiary are exclusive or non-exclusive.

        (d)   Part 2.10(d) of the Disclosure Schedule accurately identifies each NitroMed or a NitroMed Subsidiary Contract pursuant to which any Person has been granted any license under, or otherwise has received or acquired any right (whether or not currently exercisable) or interest in, any NitroMed IP Rights.

        (e)   NitroMed has delivered or made available to Deerfield a complete and accurate copy of each standard form of NitroMed IP Rights Agreement used by NitroMed or a NitroMed Subsidiary, including each standard form of (i) license agreement; (ii) employee agreement containing intellectual property assignment or license of NitroMed IP Rights or any confidentiality provision; (ii) consulting or independent contractor agreement containing intellectual property assignment or license of NitroMed IP Rights or any confidentiality provision; and (iii) confidentiality or nondisclosure agreement.

        (f)    NitroMed exclusively owns all right, title, and interest to and in NitroMed IP Rights (other than NitroMed IP Rights licensed to NitroMed, as identified in Part 2.10(c) of the Disclosure Schedule) free and clear of any liens. Without limiting the generality of the foregoing:

          (i)  To the Knowledge of NitroMed, all documents and instruments necessary to apply for NitroMed Registered IP have been validly executed, delivered, and filed in a timely manner with the appropriate Governmental Body.

         (ii)  To the Knowledge of NitroMed, each Person who is or was an employee or contractor of NitroMed or a NitroMed Subsidiary and who is or was involved in the creation or development of any NitroMed IP Rights has signed or has the obligation to sign a valid, enforceable agreement obligating the assignment of Intellectual Property to NitroMed and confidentiality provisions protecting trade secrets and confidential information of NitroMed. To the Knowledge of NitroMed, no current or former stockholder, officer, director, or employee of NitroMed or a NitroMed Subsidiary has any claim, right (whether or not currently exercisable), or interest to or in any NitroMed IP Rights. To the Knowledge of NitroMed, no employee of NitroMed or a NitroMed Subsidiary is (A) bound by or otherwise subject to any Contract restricting him or her from performing his or her duties for NitroMed or (B) in breach of any Contract with any former employer or other Person concerning NitroMed IP Rights or confidentiality provisions protecting trade secrets and confidential information in NitroMed IP Rights.

        (iii)  NitroMed has taken all reasonable steps to maintain the confidentiality of and otherwise protect and enforce its rights in all proprietary information that NitroMed holds, or purports to hold, as a trade secret.

        (iv)  NitroMed has not assigned or otherwise transferred ownership of, or agreed to assign or otherwise transfer ownership of, any NitroMed IP Rights to any other Person.

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         (v)  NitroMed is not now nor has it ever been a member or promoter of, or a contributor to, any industry standards body or similar organization that could require or obligate NitroMed to grant or offer to any other Person any license or right to any NitroMed IP Rights.

        (g)   To NitroMed's Knowledge, all NitroMed Registered IP is valid and enforceable. Without limiting the generality of the foregoing, to NitroMed's Knowledge:

          (i)  Each U.S. patent application and U.S. patent in which NitroMed or a NitroMed Subsidiary has or purports to have an ownership interest was filed within one year of the first printed publication, public use, or offer for sale of each invention claimed in the U.S. patent application or U.S. patent. Each foreign patent application and foreign patent in which NitroMed or a NitroMed Subsidiary has or purports to have an ownership interest was filed or claims priority to a patent application filed prior to each invention claimed in the foreign patent application or foreign patent being first made available to the public.

         (ii)  No registered trademark or trade name owned, used, or applied for by NitroMed conflicts or interferes with any registered trademark or trade name owned, used, or applied for by any other Person. None of the goodwill associated with or inherent in any registered trademark in which NitroMed or a NitroMed Subsidiary has or purports to have an ownership interest has been impaired.

        (iii)  Each item of NitroMed IP Rights that is NitroMed Registered IP is and at all times has been filed and maintained, as applicable, in compliance with all applicable Legal Requirements.

        (iv)  No interference, opposition, reissue, reexamination, or other proceeding is pending or threatened, in which the scope, validity, or enforceability of any NitroMed IP Rights is being, has been, or could reasonably be expected to be contested or challenged.

        (h)   Part 2.10(h) of the Disclosure Schedule accurately identifies, and NitroMed has delivered or made available to Deerfield a complete and accurate copy of, each letter that has been sent or otherwise delivered in the last five (5) years by or to NitroMed or a NitroMed Subsidiary or any director or officer of NitroMed or a NitroMed Subsidiary to a third party regarding any actual, alleged, or suspected infringement or misappropriation of any NitroMed IP Rights, and provides a brief description of the current status of the matter referred to in such letter, communication, or correspondence.

        (i)    Neither the execution, delivery, or performance of this Agreement (or any of the agreements contemplated by this Agreement) nor the consummation of any of the Contemplated Transactions will, with or without notice or lapse of time, result in, or give any other Person the right or option to cause or declare, (A) a loss of, or Encumbrance on, any NitroMed IP Rights; (B) a breach by NitroMed or a NitroMed Subsidiary of any license agreement listed or required to be listed in Part 2.10(c) of the Disclosure Schedule; (C) the release, disclosure, or delivery of any NitroMed IP Rights by or to any escrow agent or other Person; or (D) the grant, assignment, or transfer to any other Person of any license or other right or interest under, to, or in any of NitroMed IP Rights.

        (j)    NitroMed has made available to Deerfield the identity of the third-party patents and patent applications found during all freedom to operate searches that were conducted by NitroMed or a NitroMed Subsidiary. Except as disclosed therein, to NitroMed's Knowledge, NitroMed or a NitroMed Subsidiary has never infringed (directly, contributorily, by inducement, or otherwise), misappropriated, or otherwise violated any Intellectual Property rights of any other Person.

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Without limiting the generality of the foregoing, except as disclosed in the freedom to operate searches made available to Deerfield pursuant to this Section 2.10(j), to NitroMed's Knowledge:

          (i)  No product or service that has been developed or that is being commercially sold by NitroMed as specified in Part 2.10(a) of the Disclosure Schedule, nor the performance of making, using, selling or offering for sale or importation of any such product or service, has infringed, misappropriated, or otherwise violated the Intellectual Property rights of any other Person.

         (ii)  No infringement, misappropriation, or similar claim or Legal Proceeding related to the infringement, misappropriation or other violation of the Intellectual Property rights of any other Person is pending or threatened against NitroMed, a NitroMed Subsidiary or against any other Person who may be entitled to be indemnified, defended, held harmless, or reimbursed by NitroMed with respect to such claim or Legal Proceeding.

        (iii)  NitroMed has never assumed, or agreed to discharge or otherwise take responsibility for, any existing or potential liability of another Person for infringement, misappropriation, or violation of any Intellectual Property right.

        (k)   No claim or Legal Proceeding involving any NitroMed IP Rights is pending or, to NitroMed's Knowledge, has been threatened, except for any such claim or Legal Proceeding that, if adversely determined, would not adversely affect (i) the use or exploitation of NitroMed IP Rights by NitroMed or a NitroMed Subsidiary, or (ii) the manufacturing, distribution, or sale of any product or service being developed by NitroMed or a NitroMed Subsidiary, or that is being commercially sold by NitroMed or a NitroMed Subsidiary.

        2.11     Contracts .    

        (a)   Part 2.11(a) of the Disclosure Schedule identifies each NitroMed Contract, including:

          (i)  each NitroMed Contract relating to the employment of, or the performance of employment-related services by, any Person, including any employee, consultant or independent contractor;

         (ii)  each NitroMed Contract relating to the acquisition, transfer, use, development, sharing or license of any technology or any Intellectual Property or NitroMed IP Rights;

        (iii)  each NitroMed Contract imposing any restriction on NitroMed's or any NitroMed Subsidiary's right or ability (A) to compete with any other Person, (B) to acquire any product or other asset or any services from any other Person, to sell any product or other asset to, or perform any services for, any other Person or to transact business or deal in any other manner with any other Person, or (C) develop or distribute any technology;

        (iv)  each NitroMed Contract creating or involving any agency relationship, distribution arrangement or franchise relationship;

         (v)  each NitroMed Contract involving or incorporating any guaranty, any pledge, any performance or completion bond, any indemnity or any surety arrangement;

        (vi)  each NitroMed Contract creating or relating to any collaboration or joint venture or any sharing of technology, revenues, profits, losses, costs or liabilities, including NitroMed Contracts involving investments by NitroMed in, or loans by NitroMed to, any other Entity;

       (vii)  each NitroMed Contract relating to the purchase or sale of any product or other asset by or to, or the performance of any services by or for, or otherwise involving as a counterparty, any NitroMed Related Party;

      (viii)  each NitroMed Contract relating to indebtedness for borrowed money;

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        (ix)  each NitroMed Contract related to the acquisition or disposition of material assets of NitroMed or any NitroMed Subsidiary or any other Person;

         (x)  any other NitroMed Contract that (i) has a term of more than 60 days and that may not be terminated by NitroMed (without penalty) within 60 days after the delivery of a termination notice by NitroMed or (ii) that contemplates or involves (A) the payment or delivery of cash or other consideration in an amount or having a value in excess of $100,000 in the aggregate, or (B) the purchase or sale of any product, or performance of services by or to NitroMed having a value in excess of $100,000 in the aggregate;

        (xi)  each NitroMed Contract constituting a commitment of any Person to purchase products (including products in development) of NitroMed or any NitroMed Subsidiary; and

       (xii)  each NitroMed Contract with any Person, including without limitation any financial advisor, broker, finder, investment banker or other Person, providing advisory services to NitroMed or any NitroMed Subsidiary in connection with the Contemplated Transactions.

        (b)   NitroMed has delivered or made available to Deerfield accurate and complete (except for applicable redactions thereto) copies of all material written NitroMed Contracts, including all amendments thereto. Each NitroMed Contract is valid and in full force and effect, is enforceable by NitroMed or the applicable NitroMed Subsidiary in accordance with its terms, subject to applicable bankruptcy, insolvency, reorganization, moratorium or other laws relating to or affecting the rights and remedies of creditors generally and to general principles of equity (regardless of whether considered in a proceeding in equity or at law), except to the extent that (i) they have previously expired in accordance with their terms or (ii) the failure to be in full force and effect, individually or in the aggregate, would not reasonably be expected to have an NitroMed Material Adverse Effect.

        (c)   Neither NitroMed nor any NitroMed Subsidiary has materially violated or breached, or committed any material default under, any NitroMed Contract, and, to the Knowledge of NitroMed, no other Person has violated or breached, or committed any default under, any NitroMed Contract which would reasonably expected to have a NitroMed Material Adverse Effect.

        (d)   Neither NitroMed nor any NitroMed Subsidiary has received any written notice or other communication regarding any actual or possible violation or breach of, or default under, any NitroMed Contract.

        (e)   Part 2.11(e) of the Disclosure Schedule identifies and provides a brief description of each proposed Contract as to which any bid, offer, award, written proposal, term sheet or similar document has been submitted or received by NitroMed (other than term sheets provided by NitroMed or to NitroMed by any third party related to the subject matter of this transaction).

        (f)    Part 2.11(f) of the Disclosure Schedule provides an accurate and complete list of all Consents required under any NitroMed Contract to consummate the Merger and the other Contemplated Transactions.

        2.12     Tax Matters .    

        (a)   All Tax Returns required to be filed by or on behalf of NitroMed or any NitroMed Subsidiary with any Governmental Body with respect to any taxable period ending on or before the Closing Date (the " NitroMed Returns ") (i) have been or will be filed on or before the applicable due date (including any extensions of such due date), and (ii) have been, or will be when filed, accurate and complete in all material respects. All Taxes due on or before the Closing Date have been or will be paid on or before the Closing Date. NitroMed has delivered or made available to Deerfield accurate and complete copies of all NitroMed Returns filed for the last three years or which have been requested by Deerfield. NitroMed shall establish in its books and records, in the

16

Ordinary Course of Business, and shall take into account in the determination of Net Cash, reserves adequate for the payment of all unpaid Taxes by NitroMed or any NitroMed Subsidiary for the period from January 1, 2008 through the Measurement Date.

        (b)   The audited consolidated balance sheets of NitroMed as of December 31, 2005, 2006 and 2007 and the unaudited balance sheet of NitroMed as of September 30, 2008 fully accrue all liabilities for unpaid Taxes of NitroMed and each NitroMed Subsidiary with respect to all periods through the dates thereof in accordance with GAAP.

        (c)   No NitroMed Return has been examined or audited by any Governmental Body within the past ten (10) years and no examination or audit of any NitroMed Return is currently in progress or, to the Knowledge of NitroMed, threatened or contemplated. NitroMed has delivered or made available to Deerfield accurate and complete copies of all audit reports, private letter rulings, revenue agent reports, information document requests, notices of proposed deficiencies, deficiency notices, protests, petitions, closing agreements, settlement agreements, pending ruling requests and any similar documents submitted by, received by, or agreed to by or on behalf of NitroMed or any NitroMed Subsidiary relating to NitroMed Returns within the past ten (10) years. Within the past ten (10) years, no extension or waiver of the limitation period applicable to any of the NitroMed Returns has been granted (by NitroMed, any NitroMed Subsidiary or any other Person), and no such extension or waiver has been requested from NitroMed or any NitroMed Subsidiary. All Taxes that NitroMed or any NitroMed Subsidiary was required by law to withhold or collect at any time within the ten-year period ending with the Closing Date have been or will be duly withheld or collected and, to the extent required, have been or will be properly paid to the appropriate Governmental Body. Neither NitroMed nor any NitroMed Subsidiary has executed or filed any power of attorney with any taxing authority within the past ten (10) years.

        (d)   No claim or Legal Proceeding is pending or, to the Knowledge of NitroMed, has been threatened against or with respect to NitroMed or any NitroMed Subsidiary in respect of any Tax Return (including any claim that a Tax Return was required to be filed) or any Tax. There are no unsatisfied liabilities for Taxes with respect to any notice of deficiency or similar document received by NitroMed or any NitroMed Subsidiary with respect to any Tax (other than liabilities for Taxes asserted under any such notice of deficiency or similar document which are being contested in good faith by NitroMed or the applicable NitroMed Subsidiary and with respect to which adequate reserves for payment have been taken into account in the determination of Net Cash). There are no liens for Taxes upon any of the assets of NitroMed or any NitroMed Subsidiary except liens for current Taxes not yet due and payable. Neither NitroMed nor any NitroMed Subsidiary has entered into or become bound by any agreement or consent pursuant to Section 341(f) of the Code. NitroMed has not been, and NitroMed will not be, required to include any adjustment in taxable income for any tax period (or portion thereof) pursuant to Section 481 or 263A of the Code or any comparable provision under state or foreign Tax laws as a result of transactions or events occurring, or accounting methods employed, prior to the Closing Date.

        (e)   Neither NitroMed nor any NitroMed Subsidiary has (i) ever been a member of an affiliated group (within the meaning of Section 1504(a) of the Code) filing (or which it has been required to file) a consolidated federal income Tax Return or a combined state or local Tax Return (in each case, other than a group of which only NitroMed and the current NitroMed Subsidiaries were members), (ii) any liability for the Taxes of any person under Section 1.1502-6 of the Treasury Regulations (or any similar provision of state, local or foreign law), as a transferee or successor, or otherwise, and (iii) ever been a party to any joint venture, collaboration, partnership or other agreement that could be treated as a partnership for Tax purposes. Neither NitroMed nor any NitroMed Subsidiary is or has ever been, a party to or bound by any Tax indemnity agreement, Tax-sharing agreement, Tax allocation agreement or similar Contract. Neither NitroMed nor any NitroMed Subsidiary has been either a "distributing corporation" or a "controlled corporation" in

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a distribution of stock intended to qualify for tax-free treatment under Section 355 of the Code (y) in the two years prior to the date of this Agreement or (z) which could otherwise constitute part of a "plan" or "series of related transactions" (within the meaning of Section 355(e) of the Code) in conjunction with the Merger.

        (f)    None of the assets of NitroMed or any NitroMed Subsidiary (i) is property that is required to be treated as being owned by any other Person pursuant to the provisions of former Section 168(f)(8) of the Internal Revenue Code of 1954, (ii) is "tax-exempt use property" within the meaning of Section 168(h) of the Code, (iii) directly or indirectly secures any debt the interest on which is tax exempt under Section 103(a) of the Code, or (iv) is subject to a lease under Section 7701(h) of the Code or under any predecessor section.

        (g)   Neither NitroMed nor any NitroMed Subsidiary has ever participated in an international boycott as defined in Section 999 of the Code.

        (h)   No NitroMed Subsidiary is or has been a passive foreign investment company ("PFIC") within the meaning of Sections 1291-1297 of the Code or a "controlled foreign corporation" ("CFC") within the meaning of Section 957 of the Code, and neither NitroMed nor any NitroMed Subsidiary is a shareholder of a PFIC or a CFC.

        (i)    Neither NitroMed nor any NitroMed Subsidiary has incurred (or been allocated) an "overall foreign loss" as defined in Section 904(f)(2) of the Code which has not been previously recaptured in full as provided in Sections 904(f)(1) and/or 904(f)(3) of the Code.

        (j)    Neither NitroMed nor any NitroMed Subsidiary is a party to a gain recognition agreement under Section 367 of the Code.

        (k)   Neither NitroMed nor any NitroMed Subsidiary will be required to include any item of income in, or exclude any item of deduction from, taxable income for any period (or any portion thereof) ending after the Closing Date as a result of any (i) deferred intercompany gain or any excess loss account described in Treasury Regulations under Section 1502 of the Code (or any corresponding provision of state, local or foreign Tax law), (ii) closing agreement as described in Section 7121 of the Code (or any corresponding or similar provision of state, local or foreign Tax law) executed on or prior to the Closing Date, (iii) installment sale or other open transaction disposition made on or prior to the Closing Date, or (iv) prepaid amount received on or prior to the Closing Date.

        (l)    Neither NitroMed nor any NitroMed Subsidiary is or ever has been a party to a transaction or agreement that is in conflict with the Tax rules on transfer pricing in any relevant jurisdiction.

        (m)  Part 2.12(m) of the Disclosure Schedule sets forth a complete and accurate list of any NitroMed Subsidiaries for which a "check-the-box" election under Section 7701 has been made.

        (n)   Neither NitroMed nor any NitroMed Subsidiary has engaged in any "listed transaction" for purposes of Treasury Regulation sections 1.6011-4(b)(2) or 301.6111-2(b)(2) or any analogous provision of state or local law.

        (o)   Neither NitroMed nor any NitroMed Subsidiary is or has been at any time during the 5-year period ending with the Effective Time, a "United States real property holding corporation" within the meaning of Section 897(c)(2) of the Code.

        2.13     Employee and Labor Matters; Benefit Plans .    

        (a)   Part 2.13(a) of the Disclosure Schedule accurately sets forth, with respect to each employee of NitroMed or any NitroMed Subsidiary (including any employee of NitroMed or any

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NitroMed Subsidiary who is on a leave of absence) with an annual base salary in excess of $200,000:

          (i)  the name of such employee and the date as of which such employee was originally hired by NitroMed or any NitroMed Subsidiary;

         (ii)  such employee's title;

        (iii)  the aggregate dollar amount of the wages, salary, and bonuses received by such employee from NitroMed or any NitroMed Subsidiary with respect to services performed in 2008;

        (iv)  any Governmental Authorization that is held by such employee and that relates to or is useful in connection with NitroMed's business or any NitroMed Subsidiary's business;

         (v)  to the Knowledge of NitroMed, such employee's citizenship status (whether such employee is a U.S. citizen or otherwise) and, with respect to non-U.S. citizens, identifies the visa or other similar Permit under which such employee is working for NitroMed or any NitroMed Subsidiary and the dates of issuance and expiration of such visa or other Permits; and

        (vi)  such employee's primary office location.

        (b)   Except as required by COBRA, Part 2.13(b) of the Disclosure Schedule accurately identifies each former employee of NitroMed or any NitroMed Subsidiary who is receiving or is scheduled to receive (or whose spouse or other dependent is receiving or is scheduled to receive) any benefits (from NitroMed or any NitroMed Subsidiary) relating to such former employee's employment with NitroMed or any NitroMed Subsidiary; and Part 2.13(b) of the Disclosure Schedule accurately describes such benefits.

        (c)   The employment of NitroMed's and each NitroMed Subsidiary's employees is terminable by NitroMed or the applicable NitroMed Subsidiary at will. NitroMed has delivered or made available to Deerfield accurate and complete copies of all employee manuals and handbooks, disclosure materials, policy statements and other materials governing the terms and conditions of the employment of the employees of NitroMed or any NitroMed Subsidiary.

        (d)   To the Knowledge of NitroMed:

          (i)  no Key Employee of NitroMed or any NitroMed Subsidiary intends to terminate his employment with NitroMed or the applicable NitroMed Subsidiary;

         (ii)  no Key Employee of NitroMed or any NitroMed Subsidiary has received an offer that remains outstanding to join a business that may be competitive with NitroMed's or any NitroMed Subsidiary's business; and

        (iii)  no employee of NitroMed or any NitroMed Subsidiary is a party to or is bound by any confidentiality agreement, noncompetition agreement or other Contract (with any Person) that may have an adverse effect on: (A) the performance by such employee of any of his duties or responsibilities as an employee of NitroMed or the applicable NitroMed Subsidiary; or (B) NitroMed's or any NitroMed Subsidiary's business or operations.

        (e)   Neither NitroMed nor any NitroMed Subsidiary is a party to or bound by, and neither NitroMed nor any NitroMed Subsidiary has ever been a party to or bound by any union contract, collective bargaining agreement or similar Contract.

        (f)    To the Knowledge of NitroMed, neither NitroMed nor any NitroMed Subsidiary is engaged in any unfair labor practice, and there has not been any slowdown, work stoppage, labor dispute or union organizing activity, or any similar activity or dispute, affecting NitroMed or any

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NitroMed Subsidiary, since January 1, 2005. To the Knowledge of NitroMed, there are no actions, suits, claims, labor disputes or grievances pending relating to any labor, safety, wage/hour or discrimination matters involving any employee of NitroMed or any NitroMed Subsidiary, including, without limitation, charges of unfair labor practices or discrimination complaints. To the Knowledge of NitroMed, the consummation of the Merger or any of the other Contemplated Transactions will not have a material adverse effect on NitroMed or any NitroMed Subsidiary's labor relations.

        (g)   Part 2.13(g) of the Disclosure Schedule lists any independent contractors who have provided services to NitroMed or any NitroMed Subsidiary for a period of six consecutive months or longer since January 1, 2005.

        (h)   Part 2.13(h) of the Disclosure Schedule identifies each NitroMed Plan sponsored, maintained, contributed to or required to be contributed to by NitroMed or any NitroMed Subsidiary for the benefit of any current or former employee of NitroMed or any NitroMed Subsidiary. Except to the extent required to comply with Legal Requirements, neither NitroMed nor any NitroMed Subsidiary intends or has committed to establish or enter into any new NitroMed Plan, or to modify any NitroMed Plan.

        (i)    NitroMed has delivered or made available to Deerfield: (i) correct and complete copies of all documents setting forth the terms of each NitroMed Plan, including all amendments thereto and all related trust documents; (ii) the three most recent annual reports (Form Series 5500 and all schedules and financial statements attached thereto), if any, required under ERISA or the Code in connection with each NitroMed Plan; (iii) if the NitroMed Plan is subject to the minimum funding standards of Section 302 of ERISA or Section 412 of the Code, the most recent annual actuarial and funding report for such NitroMed Plan; (iv) the most recent summary plan description together with the summaries of material modifications thereto, if any, required under ERISA with respect to each NitroMed Plan; (v) all material written Contracts relating to each NitroMed Plan, including administrative service agreements and group insurance contracts; (vi) all written materials provided to any employee of NitroMed or any NitroMed Subsidiary relating to any NitroMed Plan and any proposed NitroMed Plans, in each case, relating to any amendments, terminations, establishments, increases or decreases in benefits, acceleration of payments or vesting schedules or other events that would result in any liability to NitroMed or any NitroMed Subsidiary; (vii) all material correspondence to or from any Governmental Body relating to any NitroMed Plan; (viii) the form of all COBRA forms and related notices; (ix) all insurance policies in the possession of NitroMed or any NitroMed Subsidiary pertaining to fiduciary liability insurance covering the fiduciaries for each NitroMed Plan; (x) all discrimination tests required under the Code for each NitroMed Plan intended to be qualified under Section 401(a) of the Code for the three most recent plan years; and (xi) the most recent Internal Revenue Service determination or opinion letter issued with respect to each NitroMed Plan intended to be qualified under Section 401(a) of the Code.

        (j)    NitroMed and each NitroMed Subsidiary has performed all material obligations required to be performed by it under each NitroMed Plan and is not in default under or violation of, and NitroMed has no Knowledge of any default under or violation by any other party of, the terms of any NitroMed Plan. Each NitroMed Plan has been established and maintained substantially in accordance with its terms and in substantial compliance with all applicable Legal Requirements, including ERISA and the Code. Any NitroMed Plan intended to be qualified under Section 401(a) of the Code has obtained a favorable determination letter (or opinion letter, if applicable) as to its qualified status under the Code and nothing has occurred since the issuance of such that would reasonably be expected to cause the loss of such qualified status. No "prohibited transaction," within the meaning of Section 4975 of the Code or Sections 406 and 407 of ERISA, and not otherwise exempt under Section 408 of ERISA, has occurred with respect to any NitroMed Plan

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subject to ERISA or Section 4975 of the Code that would reasonably be expected to result in material liability to NitroMed or any NitroMed Subsidiary. There are no claims or Legal Proceedings pending, or, to the Knowledge of NitroMed, threatened or reasonably anticipated (other than routine claims for benefits), against any NitroMed Plan or against the assets of any NitroMed Plan. Each NitroMed Plan (other than any NitroMed Plan to be terminated prior to