GUARANTOR SECURITY AGREEMENT

GUARANTOR SECURITY AGREEMENT

THIS GUARANTOR SECURITY AGREEMENT (this “ Security Agreement ”) is made as of September 5, 2008, by and between OptimizeRx Corporation, a Michigan corporation (“ Debtor ”), and Vicis Capital Master Fund   (“ Vicis ”), a sub-trust of Vicis Capital Series Master Trust, a unit trust organized and existing under the laws of the Cayman Islands.

WHEREAS, Debtor is a wholly owned subsidiary of OptimizeRx, a Nevada corporation (“ Issuer ”).

WHEREAS, pursuant to a Securities Purchase Agreement of even date herewith by and between Vicis and Issuer (as amended or modified from time to time, the “ Purchase Agreement ”), Issuer has issued $3,500,000 in shares of the Issuer’s Series A Convertible Preferred Stock, par value $.001 per share (the “ Preferred Shares ”), to Vicis

WHEREAS, it is a condition precedent to Vicis’s acquisition of the Preferred Shares that the Debtor execute and deliver to Vicis a security agreement in the form hereof to secure its obligations, covenants and agreements contained in its Guaranty, dated of even date herewith, in favor of Vicis.

WHEREAS, this is the Guarantor Security Agreement referred to in the Purchase Agreement.

NOW, THEREFORE, in consideration of the recitals and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, Guarantor hereby agrees with Vicis as follows:

ARTICLE I

DEFINITIONS

Capitalized terms not defined herein shall have the meaning given to them in the Purchase Agreement.  Capitalized terms not otherwise defined herein and defined in the UCC shall have, unless the context otherwise requires, the meanings set forth in the UCC as in effect on the date hereof (except that the term “ document ” shall only have the meaning set forth in the UCC for purposes of clause (d) of the definition of Collateral), the recitals and as follows:

1.1       Accounts .  “Accounts” shall mean all accounts, including without limitation all rights to payment for goods sold or services rendered that are not evidenced by instruments or chattel paper, whether or not earned by performance, and any associated rights thereto.

1.2       Collateral .  “Collateral” shall mean, subject to any limitations or qualifications set forth in this definition or in Section 2.1 hereof, all personal properties and assets of Debtor, wherever located, whether tangible or intangible, and whether now owned or hereafter acquired or arising, including without limitation:

(a)      all Inventory and documents relating to Inventory;

(b)      all Accounts and documents relating to Accounts;

(c)      all equipment, fixtures and other goods, including without limitation machinery, furniture and trade fixtures;

(d)      all general intangibles (including without limitation, software, customer lists, sales records and other business records, and licenses, permits, franchises, patents, copyrights, trademarks, and goodwill of the business in which the trademark is used, trade names, or rights to any of the foregoing), promissory notes, chattel paper, documents, letter-of-credit rights and instruments;

(e)      all motor vehicles;

(f)      (i) all deposit accounts and (ii) all cash and cash equivalents deposited with or delivered to Vicis from time to time and pledged as additional security for the Obligations;

(g)      all investment property;

(h)      all commercial tort claims; and

(i)      all additions and accessions to, all spare and repair parts, special tools, equipment and replacements for, and all supporting obligations, proceeds and products of, any and all of the foregoing assets described in Sections (a) through (h), inclusive, above.

1.3       Event of Default.  “Event of Default” shall have the meaning specified in the Purchase Agreement.

1.4       Inventory .  “Inventory” shall mean all inventory, including without limitation all goods held for sale, lease or demonstration or to be furnished under contracts of service, goods leased to others, trade-ins and repossessions, raw materials, work in process and materials used or consumed in Debtor’s business, including, without limitation, goods in transit, wheresoever located, whether now owned or hereafter acquired by Debtor, and shall include such property the sale or other disposition of which has given rise to Accounts and which has been returned to or repossessed or stopped in transit by Debtor.

1.5       Obligations .  “Obligations” shall mean all debts, liabilities, obligations, covenants and agreements of Debtor contained in the Guaranty, dated of even date herewith, by Debtor in favor of Vicis.

1.6       Person .  “Person” shall mean and include an individual, partnership, corporation, trust, unincorporated association and any unit, department or agency of government.

1.7       Security Agreement .  “Security Agreement” shall mean this Guarantor Security Agreement, together with the schedules attached hereto, as the same may be amended, supplemented or otherwise modified from time to time in accordance with the terms hereof.

1.8       Security Interest .  “Security Interest” shall mean the security interest of Vicis in the Collateral granted by Debtor pursuant to this Security Agreement.

1.9       UCC .  “UCC” shall mean the Uniform Commercial Code as adopted in Michigan and in effect from time to time.

ARTICLE II

THE SECURITY INTEREST; REPRESENTATIONS AND WARRANTIES

2.1       The Security Interest .

(a)      To secure the full and complete payment and performance when due (whether at stated maturity, by acceleration, or otherwise) of each of the Obligations, Debtor hereby grants to Vicis, subject to Section 2.1(b) hereof, a second-priority, subordinated security interest in all of Debtor’s right, title and interest in and to the Collateral.

(b)      Notwithstanding Section 2.1(a) above, Vicis hereby agrees that, in the event that Debtor and/or any of its subsidiaries should incur any Permitted Senior Indebtedness in accordance with the terms of the Securities Purchase Agreement, Vicis, at the option or discretion of the lender extending the financing facility underlying the Permitted Senior Indebtedness, promptly will release or expressly subordinate to such lender Vicis’ Security Interest, if any, in Accounts, security interests in client assets, loan documents, reserve accounts and the proceeds thereof, in each case to the extent that any of the foregoing secures Debtor’s or any of its subsidiaries’ obligations under any Permitted Senior Indebtedness.

2.2       Representations and Warranties .  Debtor hereby represents and warrants to Vicis that:

(a)      The records of Debtor with respect to the Collateral are presently located only at the address(es) listed on Schedule 1 attached to this Security Agreement.

(b)      The Collateral is presently located only at the location(s) listed on Schedule 1 attached to this Security Agreement.

(c)      The chief executive office and chief place(s) of business of Debtor are presently located at the address(es) listed on Schedule 1 to this Security Agreement.

(d)      Debtor is a Michigan corporation, and its exact legal name is set forth in the definition of “Debtor” in the introductory paragraph of this Security Agreement.  The organization identification number of Debtor is listed on Schedule 1 to this Security Agreement.

(e)      All of Debtor’s present patents and trademarks, if any, including those that have been registered with, or for which an application for registration has been filed in, the United States Patent and Trademark Office are listed on Schedule 2 attached to this Security Agreement.  All of Debtor’s present copyrights registered with, or for which an application for registration has been filed in, the United States Copyright Office or any similar office or agency of any state or any other country are listed on Schedule 2 attached to this Security Agreement.

(f)      Debtor has good title to, or valid leasehold interest in, all of the Collateral, and there are no Liens on any of the Collateral except Permitted Liens.

2.3       Authorization to File Financing Statements .  Debtor hereby   irrevocably authorizes Vicis at any time and from time to time to file in any UCC jurisdiction any initial financing statements and amendments thereto that contain any information required by part 5 of Article 9 of the UCC for the sufficiency of filing office acceptance of any financing statement or amendment, including whether Debtor is an organization, the type of organization and any state or federal organization identification number issued to Debtor.  Debtor agrees to furnish any such information to Vicis promptly upon written request.

ARTICLE III

AGREEMENTS OF DEBTOR

From and after the date of this Security Agreement, and until all of the Obligations are paid in full, Debtor shall:

3.1       Sale of Collateral .  Not sell, lease, transfer or otherwise dispose of Collateral or any interest therein, except as provided for in the Securities Purchase Agreement and for sales of Inventory in the ordinary course of business.

3.2       Maintenance of Security Interest .

(a)      At the expense of Debtor, defend the Security Interest against any and all claims of any Person adverse to Vicis (but only to the extent the claim of such adverse Person is subordinate or junior to the interest of Vicis) and take such action and execute such financing statements and other documents as Vicis may from time to time reasonably request in writing to maintain the perfected status of the Security Interest.  Debtor shall not further encumber or grant a security interest in any of the Collateral except as provided for in the Securities Purchase Agreement.