WARRANT TO PURCHASE COMMON STOCK OF CUMBERLAND PHARMACEUTICALS, INC.

EXHIBIT 4.4

THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED. SUCH SECURITIES HAVE BEEN ACQUIRED FOR INVESTMENT AND MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED, PLEDGED OR HYPOTHECATED IN THE ABSENCE OF AN EFFECTIVE REGISTRATION STATEMENT COVERING SUCH SECURITIES UNDER THE SECURITIES ACT OR AN OPINION OF COUNSEL SATISFACTORY TO THE COMPANY THAT SUCH REGISTRATION IS NOT REQUIRED.

WARRANT TO PURCHASE
COMMON STOCK OF
CUMBERLAND PHARMACEUTICALS, INC.
(Void after April 6, 2016)

     THIS WARRANT TO PURCHASE COMMON STOCK OF CUMBERLAND PHARMACEUTICALS, INC. (the " Warrant ") is issued as of this 6th day of April, 2006, by CUMBERLAND PHARMACEUTICALS, INC., a Tennessee corporation, having a place of business at 2525 West End Avenue, Suite 950, Nashville, Tennessee 37203 (the " Company "), to BANK OF AMERICA, N.A., a national banking association (Bank of America, N.A. and any subsequent assignee or transferee hereof are hereinafter referred to collectively as the " Holder ").

AGREEMENT:

     For and in consideration of the Holder making available to the Company (i) a revolving credit facility in the maximum principal amount of Four Million and No/100ths Dollars ($4,000,000.00) (the " Line of Credit ") and (ii) a term loan facility in the original principal amount of Five Million Five Hundred Thousand and No/100ths Dollars ($5,500,000) (the " Term Loan " and together with the " Line of Credit ", the " Loans ") pursuant to the terms of (i) a Fourth Amended and Restated Promissory Note (Revolving) of even date herewith in the maximum principal amount of Four Million and No/100ths Dollars ($4,000,000) (together with any and all extensions, modifications, replacements and renewals thereof, the " Line of Credit Note "), (ii) Secured Term Promissory Note of even date herewith in the original principal amount of Five Million Five Hundred Thousand and No/100ths Dollars ($5,500,000) (together with any and all extensions, modifications, replacements and renewals thereof, the " Term Note "; and together with the Line of Credit Note, the " Notes ") and (iii) a Second Amended and Restated Loan Agreement of even date herewith (as amended, supplemented or otherwise modified from time to time, the " Loan Agreement "; any capitalized terms used but not otherwise defined herein shall have the same meanings as in the Loan Agreement), and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Company hereby grants to the Holder the right to purchase from the Company at a per share price equal to $18.00 (the " Exercise Price "), 1,979 shares of the Company’s common stock, $0 par value per share (the " Common Stock "), at any time or from time to time, from April 6, 2006 up to and including 5:00 p.m. (Central time) on April 6, 2016 (the " Expiration Date "), upon surrender to the Company at its principal office (or at such other location as the Company may advise the Holder in writing) of this Warrant properly endorsed with the Notice of Exercise attached hereto as Exhibit A , duly

completed and signed and, if applicable, upon payment in cash or by check acceptable to the Company of the aggregate Exercise Price for the number of shares for which this Warrant is being exercised determined in accordance with the provisions hereof. The Exercise Price and the number of shares purchasable hereunder are subject to adjustment as provided in Section 3 of this Warrant.

     This Warrant is subject to the following terms and conditions:

      1. Exercise; Issuance of Certificates; Payment for Shares.

           1.1 General. This Warrant is exercisable at the option of the Holder, at any time or from time to time, from the date of the issuance of this Warrant up to the Expiration Date, for all or any part of the shares of Common Stock (but not for a fraction of a share) that maybe purchased hereunder. The Company agrees that the shares of Common Stock purchased under this Warrant shall be and are deemed to be issued to the Holder as the record owner of such shares as of the close of business on the date on which this Warrant shall have been surrendered to the Company, properly endorsed, the completed, executed Form of Subscription shall have been delivered and any required payment made for such shares. Certificates for the shares of Common Stock so purchased, together with any other securities or property to which the Holder is entitled upon such exercise, shall be delivered to the Holder by the Company at the Company’s expense within a reasonable time after the rights represented by this Warrant have been so exercised. In case of a purchase of less than all of the shares that may be purchased under this Warrant, the Company shall cancel this Warrant and execute and deliver a new Warrant or Warrants of like tenor for the balance of the shares purchasable under the Warrant surrendered upon such purchase to the Holder within a reasonable time. Each stock certificate so delivered shall be in such denominations of Common Stock as may be requested by the Holder and shall be registered in the name of such Holder.

           1.2 Net Issue Exercise. Notwithstanding any provisions herein to the contrary, if the Fair Market Value of one share of the Company’s Common Stock is greater than the Exercise Price (at the date of calculation as set forth below), in lieu of exercising this Warrant for cash, the Holder may elect to receive shares equal to the value (as determined below) of this Warrant (or the portion thereof being canceled) by surrender of this Warrant at the principal office of the Company together with the properly endorsed Form of Subscription and notice of such election in which event the Company shall issue to the Holder a number of shares of Common Stock computed using the following formula:

X=Y(A-B)
        A

     Where X = the number of shares of Common Stock to be issued to the Holder

     Y = the number of shares of Common Stock purchasable under the Warrant or, if only a portion of the Warrant is being exercised, the portion of the Warrant being canceled (at the date of such calculation)

     A = the Fair Market Value of one share of the Company’s Common Stock (at the date of such calculation)

     B = Exercise Price (as adjusted to the date of such calculation)

     The "Fair Market Value" of a share of Common Stock as of a particular date shall mean: (a) if there is an active public market for the Company’s Common Stock at the time of such exercise, the fair market value per share shall be the average of the closing prices of the Common Stock of the Company over the five (5) trading days ending immediately prior to the applicable date of valuation if traded on a securities exchange or the Nasdaq National Market; or, if actively traded over-the-counter, the average of the closing bid prices over the 30-day period ending immediately prior to the applicable date of valuation, whichever is applicable; or (b) if there is no active public market for the Company’s Common Stock at the time of such exercise, the Fair Market Value shall be the value thereof as determined in good faith by the board of directors of the Company (the " Determination "). The board of directors shall provide to the Holder a written notice of the Determination which notice shall set forth supporting data in respect of such calculation (the " Determination Notice "). Holder shall have 10 days following receipt of the Determination Notice within which to deliver to the Company a written notice of an objection, if any, to the Determination. The failure by Holder to deliver such notice within such 10-day period shall constitute the Holder’s acceptance of the Determination as conclusive. In the event of the timely delivery by Holder of its objection notice, the Company and the Holder shall attempt in good faith to arrive at an agreement with respect to the Fair Market Value of a share of Common Stock of the Company, which agreement shall be set forth in writing within 15 days following delivery of such objection notice by Holder. If the Company and the Holder are unable to reach an agreement within such 15-day period, the matter shall be promptly referred for determination to a regionally or nationally recognized investment banking or valuation firm (the " Valuer ") reasonably acceptable to the Company and the Holder. The Company and the Holder will cooperate with each other in good faith to select such Valuer. The Valuer may select the Determination or may select any other number or value. The Valuer’s selection will be furnished to the Company and the Holder in writing and be conclusive and binding upon the parties and shall not be subject to collateral attack. The fees and expenses of the Valuer shall be borne by the Company unless the Valuer’s determination of Fair Market Value per share of the Company’s Common Stock is within 10% of the Determination, in which case the Valuer’s fees and expenses shall be borne by the Holder.

Notwithstanding the foregoing, in the event the Warrant is exercised in connection with the Company’s initial public offering of Common Stock, the fair market value per share shall be the per share offering price to the public of the Company’s initial public offering.

      2. Shares to be Fully Paid; Reservation of Shares. The Company covenants and agrees that all shares of Common Stock that may be issued upon the exercise of the rights represented by this Warrant will, upon issuance, be duly authorized, validly issued, fully paid and nonassessable and free from all preemptive rights of any stockholder and free of all taxes, liens and charges with respect to the issuance thereof. The Company further covenants and agrees that during the period within which the rights represented by this Warrant may be exercised, the Company will at all times have authorized and reserved, for the purpose of issue or transfer upon exercise of the subscription rights evidenced by this Warrant, a sufficient number of shares of authorized but unissued Common Stock, or other securities and property, when and as required to provide for the exercise of the rights represented by this Warrant. The Company will take all such action as may be necessary to assure that such shares of Common Stock may be

issued as provided herein without violation of any applicable law or regulation, or of any requirements of any domestic securities exchange upon which the Common Stock may be listed; provided, however, that the Company shall not be required to effect a registration under federal or state securities laws with resp