Form of Warrant



 Exhibit 4.1 
 THESE SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933 OR THE LAWS OF ANY STATE. THEY MAY NOT BE SOLD OR OTHERWISE TRANSFERRED UNLESS THEY ARE REGISTERED UNDER SUCH ACT AND APPLICABLE STATE
SECURITIES LAWS OR AN EXEMPTION FROM REGISTRATION IS AVAILABLE. 
              Warrants 
 drugstore.com, inc. 
 WARRANT CERTIFICATE 
 Warrant No. W-     
 This warrant certificate (“Warrant
Certificate”) certifies that for value received                          or registered assigns (the
“Holder”) is the owner of the number of warrants (“Warrants”) specified above, each of which entitles the Holder thereof to purchase, at any time on or before the Expiration Date (hereinafter defined) one fully paid and
non-assessable share of Common Stock, $0.0001 par value (“Common Stock”), of drugstore.com, inc., a Delaware corporation (the “Company”), at a purchase price of $2.50 per share of Common Stock in lawful money of the United States
of America in cash or by certified or cashier’s check or a combination of cash and certified or cashier’s check, subject to adjustment as hereinafter provided. 
  

	 	1	Warrant; Purchase Price 

 Each Warrant shall entitle
the Holder to purchase one share of Common Stock of the Company and the purchase price payable upon exercise of the Warrants shall initially be $2.50 per share of Common Stock, subject to adjustment as hereinafter provided (the “Purchase
Price”). The Purchase Price and number of shares of Common Stock issuable upon exercise of each Warrant are subject to adjustment as provided in Article 6. 
  

	 	2	Exercise; Expiration Date 

 2.1 The Warrants are
exercisable, at the option of the Holder, at any time after issuance and on or before the Expiration Date, upon surrender of this Warrant Certificate to the Company together with a duly completed Notice of Exercise, in the form attached hereto as
Exhibit A, and payment of an amount equal to the Purchase Price times the number of Warrants to be exercised. In the case of exercise of less than all the Warrants represented by this Warrant Certificate, the Company shall cancel the Warrant
Certificate upon the surrender thereof and shall execute and deliver a new Warrant Certificate for the balance of such Warrants. 
  

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 2.2 The term “Expiration Date” shall mean 5:00 p.m. New York time on June 5, 2017 or if
such date shall in the State of New York be a holiday or a day on which banks are authorized to close, then 5:00 p.m. New York time the next following date that in the State of New York is not a holiday or a day on which banks are authorized to
close. 
  

	 	3	Registration and Transfer on Company Books 

 3.1 The
Company shall maintain books for the registration and transfer of the Warrants and the registration and transfer of the shares of Common Stock issued upon exercise of the Warrants. 
 3.2 Prior to due presentment for registration of transfer of this Warrant Certificate, or the shares of Common Stock issued upon exercise of the
Warrants, the Company may deem and treat the registered Holder as the absolute owner thereof. 
 3.3 Neither this Warrant nor the shares of
Common Stock issuable upon exercise hereof have been registered under the Securities Act of 1933, as amended (the “Act”). The Holder will not transfer this Warrant or issue or transfer the shares of Common Stock issuable upon exercise
hereof unless (i) there is an effective registration covering such Warrant or such shares, as the case may be, under the Act and applicable states securities laws, (ii) it first receives a letter from an attorney, acceptable to the
Company’s board of directors or its agents, stating that in the opinion of the attorney the proposed issue or transfer is exempt from registration under the Act and under all applicable state securities laws, or (iii) the transfer is made
pursuant to Rule 144 under the Act. Subject to the foregoing, this Warrant Certificate, the Warrants represented hereby, and the shares of Common Stock issued upon exercise of the Warrants, may be sold, assigned or otherwise transferred voluntarily
by the Holder to officers or directors of the Holder, to members of such persons’ immediate families, or to the Holder’s parent or subsidiary corporations. The Company shall register upon its books any permitted transfer of a Warrant
Certificate, upon surrender of same to the Company with a written instrument of transfer duly executed by the registered Holder or by a duly authorized attorney. Upon any such registration of transfer, new Warrant Certificate(s) shall be issued to
the transferee(s) and the surrendered Warrant Certificate shall be canceled by the Company. A Warrant Certificate may also be exchanged, at the option of the Holder, for new Warrant Certificates representing in the aggregate the number of Warrants
evidenced by the Warrant Certificate surrendered. 
 3.4 The Warrant and the Common Stock issuable upon exercise of the Warrant will be
acquired for investment and not with a view to the sale or distribution of any part thereof, and the Holder has no present intention of selling or engaging in any public distribution of the same except pursuant to a registration or exemption
pursuant to the 1933 Act. 
 3.5 The Holder has such knowledge and experience in financial and business matters as to be capable of
evaluating the merits and risks of its investment, and has the ability to bear the economic risks of its investment. 
  

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 3.6 Holder is an “accredited investor” within the meaning of Rule 501 of
Regulation D under the 1933 Act, as presently in effect. 
  

	 	4	Reservation of Shares 

 The Company covenants that
it will at all times reserve and keep available out of its authorized Common Stock, solely for the purpose of issuance upon exercise of the Warrants, such number of shares of Common Stock as shall then be issuable upon the exercise of all
outstanding Warrants. The Company covenants that all shares of Common Stock that shall be issuable upon exercise of the Warrants shall be duly and validly issued and, upon payment for such shares as set forth herein, fully paid and non-assessable
and free from all taxes, liens and charges with respect to the issue thereof, and that upon issuance such shares shall be listed on each national securities exchange, if any, on which the other shares of outstanding Common Stock of the Company are
then listed. 
  

	 	5	Loss or Mutilation 

 Upon receipt by the Company of
reasonable evidence of the ownership of and the loss, theft, destruction or mutilation of any Warrant Certificate and, in the case of loss, theft or destruction, of indemnity reasonably satisfactory to the Company, or, in the case of mutilation,
upon surrender and cancellation of the mutilated Warrant Certificate, the Company shall execute and deliver in lieu thereof a new Warrant Certificate representing an equal number of Warrants. 
  

	 	6	Adjustment of Purchase Price and Number of Shares Deliverable 

 6.1 The number of shares of Common Stock purchasable upon the exercise of each Warrant (such shares being referred to in this Section 6 as the “Warrant Shares”) and the Purchase Price with respect to
the Warrant Shares shall be subject to adjustment as follows: 
 (a) In case the Company shall (i) declare a dividend or make a
distribution on its Common Stock payable in shares of its capital stock, (ii) subdivide its outstanding shares of Common Stock through stock split or otherwise, (iii) combine its outstanding shares of Common Stock into a smaller number of
shares of Common Stock, or (iv) issue by reclassification of its Common Stock (including any such reclassification in connection with a consolidation or merger in which the Company is the continuing corporation) other securities of the Company,
the number and/or nature of Warrant Shares purchasable upon exercise of each Warrant immediately prior thereto shall be adjusted so that the Holder shall be entitled to receive the kind and number of Warrant Shares or other securities of the Company
which he would have owned or have been entitled to receive after the happening of any of the events described above, had such Warrant been exercised immediately prior to the happening of such event or any record date with respect thereto. An
adjustment made pursuant to this paragraph (a) shall become effective retroactively as of the record date of such event. 
 (b) In case
the Company shall issue rights, options or warrants or securities convertible into Common Stock to the holders of its shares of Common Stock generally, entitling 

  

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them (for a period expiring within forty-five (45) days after the record date referred below in this paragraph (b)) to subscribe for or purchase shares
of Common Stock at a price per share which (together with the value of the consideration, if any, paid for such rights, options, warrants or convertible securities) is lower on the record date referred to below than the then Market Price Per Share
of Common Stock (as determined pursuant to Section 9.2) the number of Warrant Shares thereafter purchasable upon the exercise of each Warrant shall be determined by multiplying the number of Warrant Shares immediately theretofore purchasable
upon exercise of each Warrant by a fraction, of which the numerator shall be the number of shares of Common Stock outstanding on such record date plus the number of additional shares of Common Stock offered for subscription or purchase, and of which
the denominator shall be the number of shares of Common Stock outstanding on such record date plus the number of shares which the aggregate offering price of the total number of shares of Common Stock so offered would purchase at the then Market
Price Per Share of Common Stock. Such adjustment shall be made whenever such rights, options, warrants or convertible securities are issued, and shall become effective retroactively as of the record date for the determination of shareholders
entitled to receive such rights, options, warrants or convertible securities. 
 (c) In case the Company shall distribute to all holders of
its shares of Common Stock, or all holders of Common Stock shall otherwise become entitled to receive, shares of capital stock of the Company (other than dividends or distributions on its Common Stock referred to in paragraph (a) above),
evidences of its indebtedness or rights, options, warrants or convertible securities providing the right to subscribe for or purchase any shares of the Company’s capital stock or evidences of its indebtedness (other than any rights, options,
warrants or convertible securities referred to in paragraph (b) above), then in each case the number of Warrant Shares thereafter purchasable upon the exercise of each Warrant shall be determined by multiplying the number of Warrant Shares
theretofore purchasable upon the exercise of each Warrant, by a fraction, of which the numerator shall be the then Market Price Per Share of Common Stock (as determined pursuant to Section 9.2) on the record date mentioned below in this
paragraph (c), and of which the denominator shall be the then Market Price Per Share of Common Stock on such record date, less the then fair value per share (as determined by the Board of Directors of the Company, in good faith) of the portion of
the shares of the Company’s capital stock other than Common Stock, evidences of indebtedness, or of such rights, options, warrants or convertible securities, distributable with respect to each share of Common Stock. Such adjustment shall be
made whenever any such distribution is made, and shall become effective retroactively as of the record date for the determination of shareholders entitled to receive such distribution. 
 (d) In the event of any capital reorganization or any reclassification of the capital stock of the Company or in case of the consolidation or merger of
the Company with another corporation (other than a consolidation or merger in which the outstanding shares of the Company’s Common Stock are not converted into or exchanged for other rights or interests), or in the case of any sale, transfer or
other disposition to another corporation of all or substantially all the properties and assets of the Company, the Holder of each Warrant shall thereafter be entitled to purchase (and it shall be a condition to the consummation of any such
reorganization, reclassification, consolidation, merger, sale, transfer or other disposition that appropriate 

  

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provisions shall be made so that such Holder shall thereafter be entitled to purchase) the kind and amount of shares of stock and other securities and
property (including cash) which the Holder would have been entitled to receive had such Warrants been exercised immediately prior to the effective date of such reorganization, reclassification, consolidation, merger, sale, transfer or other
disposition; and in any such case appropriate adjustments shall be made in the application of the provisions of this Article 6 with respect to rights and interest thereafter of the Holder of the Warrants to the end that the provisions of this
Article 6 shall thereafter be applicable, as near as reasonably may be, in relation to any shares or other property thereafter purchasable upon the exercise of the Warrants. The provisions of this Section 6.1(d) shall similarly apply to
successive reorganizations, reclassifications, consolidations, mergers, sales, transfers or other dispositions. 
 (e) Whenever the number of
Warrant Shares purchasable upon the exercise of each Warrant is adjusted, as provided in this Section 6.1, the Purchase Price with respect to the Warrant Shares shall be adjusted by multiplying such Purchase Price immediately prior to such
adjustment by a fraction, of which the numerator shall be the number of Warrant Shares purchasable upon the exercise of each Warrant immediately prior to such adjustment, and of which the denominator shall be the number of Warrant Shares so
purchasable immediately thereafter. 
 6.2 In the event the Company shall declare a dividend, or make a distribution to the holders of its
Common Stock generally, whether in cash, property or assets of any kind, including any dividend payable in stock or securities of any other issuer owned by the Company (excluding regularly payable cash dividends declared from time to time by the
Company’s Board of Directors or any dividend or distribution referred to in Section 6.1(a) or (c) above), the Purchase Price of each Warrant shall be reduced, without any further action by the parties hereto, by the Per Share Value
(as hereinafter defined) of the dividend. For purposes of this Section 6.2, the “Per Share Value” of a cash dividend or other distribution shall be the dollar amount of the distribution on each share of Common Stock and the “Per
Share Value” of any dividend or distribution other than cash shall be equal to the fair market value of such non-cash distribution on each share of Common Stock as determined in good faith by the Board of Directors of the Company. 

6.3 In case the Company shall at any time or from time to time after issuance issue any shares of Common Stock or rights to acquire Common Stock
(other than shares issued in any transactions covered by paragraph (a) of Section 6.1 hereof), for a consideration per share less than the Purchase Price with respect to the Warrant Shares in effect on the date of such issue, then,
forthwith upon such issue, the Purchase Price with respect to the Warrant Shares shall be reduced to a price determined by dividing (a) the sum of (i) the number of shares of Common Stock of the Company outstanding immediately prior to
such issue multiplied by the Purchase Price of the Warrant Shares in effect immediately prior to such issue, plus (ii) the consideration, if any, received by the Company upon such issue, by (b) the number of shares of Common Stock of the
Company outstanding immediately after such issue. In addition to such adjustment to the Purchase Price, the number of Warrant Shares purchasable under each Warrant shall be increased to a number determined by dividing (x) the number of Warrant
Shares purchasable under such Warrant immediately prior to such issue, multiplied by the Purchase Price in effect immediately 

  

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prior to such issuance, by (y) the Purchase Price of the Warrant Shares in effect immediately after the foregoing adjustment. For the purpose of the
above determination, the follow provisions shall be applicable: 
 (a) In case the Company shall in any manner issue any options, warrants or
other rights to subscribe for or to purchase shares of Common Stock, then, for the purposes of this Section 6.3, (i) all shares which the holders of such rights shall be entitled thereby to subscribe for or purchase shall be deemed to be
issued as of the date of issue of such rights, and (ii) the minimum aggregate consideration payable pursuant to such rights for the shares covered thereby, plus the consideration, if any, received by the Company for such rights, shall be deemed
to be the consideration actually received by the Company (as of the date of the issue of such rights) for the issue of the total number of shares underlying such rights. 
 (b) In case the Company shall in any manner issue any securities or obligations directly or indirectly convertible into or exchangeable for shares of Common Stock, then, for the purposes of this Section 6.3,
(i) all shares to which holders of such securities or obligations shall thereby be entitled upon conversion or exchange shall be deemed to be issued as of the date of issue of such securities or obligations, and (ii) the aggregate amount
received or receivable by the Company in consideration for the issue of such securities or obligations, plus the minimum aggregate amount of additional consideration, if any, payable upon conversion or exchange of such securities or obligations,
shall be deemed to be the consideration actually received (as of the date of the issue of such securities or obligations) for the issue of the total number of shares issuable upon conversion or exchange of such securities or obligations. 

(c) The consideration received by the Company for any shares of Common Stock, or rights to acquire Common Stock, shall be deemed to be the proceeds
received for such shares or rights, excluding cash received on account of accrued interest or accrued dividends and after deducting therefrom any and all commissions and expenses paid or incurred by the Company for any underwriting of, or otherwise
in connection with, the issue of such shares or rights. 
 (d) No adjustment of the Purchase Price of the Warrant Shares shall be made as a
result of or in connection with the issuance of (i) any shares of Common Stock issuable upon the exercise or conversion of any options, convertible securities or other rights outstanding on the date of original issuance of this Warrant
Certificate or (ii) any shares of Common Stock or options to purchase Common Stock hereafter issued in connection with any duly authorized employee stock option plan, stock purchase plan or restricted stock award plan of the Company.

 (e) For the purposes of this Section 6.3, (i) the term “issue” of shares or securities by the Company shall be deemed
to include any issuance, sale or other disposition of shares or securities of the Company, including shares held in the treasury of the Company, (ii) the term “Common Stock” shall include any capital stock of the Company other than
preferred stock with a fixed limit on dividends and a fixed amount payable in the event of any liquidation, and (iii) in no event shall the Purchase Price with respect to the Warrant Shares be increased, or the number of Warrant Shares
purchasable under any Warrant be decreased, as a result of the provisions of this Section 6.3. 
  

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 6.4 No adjustment in the number of Warrant Shares purchasable under the Warrants, or in the Purchase
Price with respect to the Warrant Shares, shall be required unless such adjustment would require an increase or decrease of at least 1% in the number of Warrant Shares issuable upon the exercise of such Warrant, or in the Purchase Price thereof;
provided, however, that any adjustments which by reason of this Section 6.4 are not required to be made shall be carried forward and taken into account in any subsequent adjustment. All final results of adjustments to the number of Warrant
Shares and the Purchase Price thereof shall be rounded to the nearest one thousandth of a share or the nearest cent, as the case may be. Anything in this Section 6 to the contrary notwithstanding, the Company shall be entitled, but shall not be
required, to make such changes in the number of Warrant Shares purchasable upon the exercise of each Warrant, or in the Purchase Price thereof, in addition to those required by such Section, as it in its discretion shall determine to be advisable in
order that any dividend or distribution in shares of Common Stock, subdivision, reclassification or combination of shares of Common Stock, issuance of rights, warrants or options to purchase Common Stock, or distribution of shares of stock other
than Common Stock, evidences of indebtedness or assets (other than distributions of cash out of retained earnings) or convertible or exchangeable securities hereafter made by the Company to the holders of its Common Stock shall not result in any tax
to the holders of its Common Stock or securities convertible into Common Stock. 
 6.5 Whenever the number of Warrant Shares purchasable upon
the exercise of each Warrant or the Purchase Price of such Warrant Shares is adjusted, as herein provided, the Company shall mail to the Holder, at the address of the Holder shown on the books of the Company, a notice of such adjustment or
adjustments, prepared and signed by the Chief Financial Officer or Secretary of the Company, which sets forth the number of Warrant Shares purchasable upon the exercise of each Warrant and the Purchase Price of such Warrant Shares after such
adjustment, a brief statement of the facts requiring such adjustment and the computation by which such adjustment was made. 
 6.6 In the
event that at any time prior to the expiration of the Warrants and prior to their exercise: 
 (a) the Company shall declare any distribution
(other than a cash dividend or a dividend payable in securities of the Company with respect to the Common Stock); or 
 (b) the Company shall
offer for subscription to the holders of the Common Stock any additional shares of stock of any class or any other securities convertible into Common Stock or any rights to subscribe thereto; or 
 (c) the Company shall declare any stock split, stock dividend, subdivision, combination, or similar distribution with respect to the Common Stock,
regardless of the effect of any such event on the outstanding number of shares of Common Stock; or 
  

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 (d) the Company shall declare a dividend, other than a dividend payable in shares of the Company’s
own Common Stock; or 
 (e) there shall be any capital change in the Company as set forth in Section 6.1(d); or 
 (f) there shall be a voluntary or involuntary dissolution, liquidation, or winding up of the Company (other than in connection with a consolidation,
merger, or sale of all or substantially all of its property, assets and business as an entity); 
 (each such event hereinafter being referred to as a
“Notification Event”), the Company shall cause to be mailed to the Holder, not less than twenty (20) days prior to the record date, if any, in connection with such Notification Event (provided, however, that if there is no record
date, or if twenty (20) days prior notice is impracticable, as soon as practicable) written notice specifying the nature of such event and the effective date of, or the date on which the books of the Company shall close or a record shall be
taken with respect to, such event. Such notice shall also set forth facts indicating the effect of such action (to the extent such effect may be known at the date of such notice) on the Purchase Price and the kind and amount of the shares of stock
or other securities or property deliverable upon exercise of the Warrants. For purposes here of, a business day shall mean any day other than a Saturday, Sunday or any other day in which commercial banks are authorized by law to be closed in New
York, New York. 
 6.7 The form of Warrant Certificate need not be changed because of any change in the Purchase Price, the number of Warrant
Shares issuable upon the exercise of a Warrant or the number of Warrants outstanding pursuant to this Section 6, and Warrant Certificates issued before or after such change may state the same Purchase Price, the same number of Warrants, and the
same number of Warrant Shares issuable upon exercise of Warrants as are stated in the Warrant Certificates theretofore issued pursuant to this Agreement. The Company may, however, at any time, in its sole discretion, make any change in the form of
Warrant Certificate that it may deem appropriate and that does not affect the substance thereof, and any Warrant Certificates thereafter issued or countersigned, whether in exchange or substitution for an outstanding Warrant Certificate or
otherwise, may be in the form as so changed. 
  

	 	7	Conversion Rights 

 7.1 In lieu of exercise of any
portion of the Warrants as provided in Section 2.1 hereof, the Warrants represented by this Warrant Certificate (or any portion thereof) may, at the election of the Holder, be converted into the nearest whole number of shares of Common Stock
equal to: (1) the product of (a) the number of Warrants to be so converted, (b) the number of shares of Common Stock then issuable upon the exercise of each Warrant and (c) the excess, if any, of (i) the Market Price Per
Share (as determined pursuant to Section 9.2) with respect to the date of conversion over (ii) the Purchase Price in effect on the business day next preceding the date of conversion, divided by (2) the Market Price Per Share with
respect to the date of conversion. 
  

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 7.2 The conversion rights provided under this Section 7 may be exercised in whole or in part and at
any time and from time to time while any Warrants remain outstanding. In order to exercise the conversion privilege, the Holder shall surrender to the Company, at its offices, this Warrant Certificate accompanied by a duly completed Notice of
Conversion in the form attached hereto as Exhibit B. The Warrants (or so much thereof as shall have been surrendered for conversion) shall be deemed to have been converted immediately prior to the close of business on the day of surrender of such
Warrant Certificate for conversion in accordance with the foregoing provisions. As promptly as practicable on or after the conversion date, the Company shall issue and shall deliver to the Holder (i) a certificate or certificates representing
the number of shares of Common Stock to which the Holder shall be entitled as a result of the conversion, and (ii) if the Warrant Certificate is being converted in part only, a new certificate in principal amount equal to the unconverted
portion of the Warrant Certificate. 
  

	 	8	Voluntary Adjustment by the Company 

 The Company
may, at its option, at any time during the term of the Warrants, reduce the then current Purchase Price to any amount deemed appropriate by the Board of Directors of the Company and/or extend the date of the expiration of the Warrants. 

 

	 	9	Fractional Shares and Warrants; Determination of Market Price Per Share 

 9.1 Anything contained herein to the contrary notwithstanding, the Company shall not be required to issue any fraction of a share of Common Stock in connection with the exercise of Warrants. Warrants may not be
exercised in such number as would result (except for the provisions of this paragraph) in the issuance of a fraction of a share of Common Stock unless the Holder is exercising all Warrants then owned by the Holder. In such event, the Company shall,
upon the exercise of all of such Warrants, issue to the Holder the largest aggregate whole number of shares of Common Stock called for thereby upon receipt of the Purchase Price for all of such Warrants and pay a sum in cash equal to the remaining
fraction of a share of Common Stock, multiplied by its Market Price Per Share (as determined pursuant to Section 9.2 below) as of the last business day preceding the date on which the Warrants are presented for exercise. 
 9.2 As used herein, the “Market Price Per Share” with respect to any date shall mean the closing price per share of Company’s Common Stock
for the trading day immediately preceding such date. The closing price for each such day shall be the last sale price regular way or, in case no such sale takes place on such day, the average of the closing bid and asked prices regular way, in
either case on the principal securities exchange on which the shares of Common Stock of the Company are listed or admitted to trading, the last sale price, or in case no sale takes place on such day, the average of the closing bid and asked prices
of the Common Stock on NASDAQ or any comparable system, or if the Common Stock is not reported on NASDAQ, or a comparable system, the average of the closing bid and asked prices as furnished by two members of the National Association of Securities
Dealers, Inc. selected from time to time by the Company for that purpose. If such bid and asked prices are not available, then “Market Price Per Share” shall be equal to the fair market value of the Company’s Common Stock as
determined in good faith by the Board of Directors of the Company. 
  

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	 	10	Registration Rights 

 10.1 No sale, transfer,
assignment, hypothecation or other disposition of the Warrant Shares shall be made unless any such transfer, assignment or other disposition will comply with the rules and statutes administered by the Securities and Exchange Commission and
(i) a registration statement under the Act, including such shares is currently in effect, or (ii) in the opinion of counsel satisfactory to the Company a current registration statement is not required for such disposition of the shares.

 10.2 The Company agrees that the Holder shall have the one-time right, beginning on the date which is six months following the
Company’s initial public offering under the Act, upon written notice to the Company, to require that the Company prepare and promptly file a registration statement, as may be required under the Act, in connection with the public offering, on a
time-to-time basis or otherwise, of not less than 50% of the then outstanding Warrant Shares. In connection therewith, the Company shall be obligated to prepare and file such registration statement within 45 days of receipt of any such initial
notice and shall be further obligated to use its reasonable best efforts, including the filing of any amendments or supplements thereto, to have any such registration statement declared effective under the Act and the rules and regulations
promulgated thereunder as soon as practicable after the filing date thereof. The Company shall also use its reasonable best efforts to keep any such registration statement, and the accompanying prospectus, effective and current under the Act at its
expense for such period of time as is not otherwise burdensome to the Company, in no event to be less than 90 days. Notwithstanding anything to the contrary in this Warrant Certificate, the Company shall not be required to register any Warrant
Shares pursuant to a request under Section 10 hereof if within twenty (20) days after its receipt of a request therefor, counsel for the Company delivers an opinion to the requesting Holder, in form and substance reasonably satisfactory to
counsel for such Holder, that the proposed sale of Warrant Shares requested to be so registered may be effected in its entirety within a ninety (90) day following such request without registration and without any further holding period pursuant
to SEC Rules 144 or 145(d) (if available). 
 10.3 In addition to the rights of the Holder pursuant to Section 10.2, the Company agrees
that, at any time or times hereafter, as and when it intends to register any of its securities under the Act other than pursuant to a registration requested pursuant to Section 10.2 hereof, whether for its own account and/or on behalf of
selling stockholders (except in connection with an offering on Form S-8 or an offering solely related to an acquisition or exchange on a Form S-4 or any subsequent similar form) the Company will notify the Holder of such intention (a
“Registration Notice”) and, upon request from the Holder, will use its reasonable best efforts to cause the Warrant Shares designated by the Holder to be registered under the Act. The number of Warrant Shares to be included in such
offering may be reduced if and to the extent that the underwriter of securities included in the registration statement and offered by the Company shall be of the opinion that such inclusion would adversely affect the marketing of the securities to
be sold by the Company therein; provided, however, that the 

  

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percentage of the reduction of such Warrant Shares shall be no greater than the percentage reduction of securities of other selling stockholders, as such
percentage reductions are determined in the good faith judgment of the Company. The Company will use its reasonable best efforts to keep each such registration statement current for such period of time as is not otherwise burdensome to the Company,
in no event to be less than 90 days. 
 10.4 Any registration statement referred to in subsection 10.2 or 10.3 hereof shall be prepared and
processed in accordance with the following terms and conditions: 
 (i) the Holder will cooperate in furnishing promptly to the Company in
writing any information requested by the Company in connection with the preparation, filing and processing of such registration statement. 
 (ii) To the extent requested by an underwriter of securities included in a registration statement referred to in Subsection 10.3 hereof and offered by the Company, the Holder will defer the sale of Warrant Shares for a period commencing
twenty (20) days prior and terminating one hundred twenty (120) days after the effective date of the registration statement, provided that any principal shareholders of the Company who also have shares included in the registration
statement will also defer their sales for a similar period. 
 (iii) The Company will furnish to the Holder such number of prospectuses or
other documents incident to such registration as may from time to time be reasonably requested, and cause its shares to be qualified under the blue-sky laws of those states reasonably requested by the Holder. 
 (iv) The Company will indemnify the Holder (and any officer, director or controlling person of the Holder) and any underwriters acting on behalf of the
Holder against all claims, losses, expenses, damages and liabilities (or actions in respect thereof) to which they may become subject under the Act or otherwise, arising out of or based upon any untrue or alleged untrue statement of any material
facts contained in any registration statement filed pursuant hereto, or any document relating thereto, including all amendments and supplements, or arising out of or based upon the omission or alleged omission to state therein a material fact
required to be stated therein or necessary to make the statements therein contained not misleading, and will reimburse the Holder (or such other aforementioned parties) or such underwriters for any legal and all other expenses reasonably incurred in
accordance with investigating or defending any such claim, loss, damage, liability or action; provided, however, that the Company will not be liable where the untrue or alleged untrue statement or omission or alleged omission is based upon
information furnished in writing to the Company by the Holder or any underwriter obtained by the Holder expressly for use therein, or as a result of the Holder’s or any such underwriter’s failure to furnish to the Company information duly
requested in writing by counsel for the Company specifically for use therein. This indemnity agreement shall be in addition to any other liability the Company may have. The indemnity agreement of the Company contained in this paragraph
(iv) shall remain operative and in full force and effect regardless of any investigation made by or on behalf of any indemnified party and shall survive the delivery of and payment for the Warrant Shares. 
  

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 (v) The Holder will indemnify the Company (and any officer, director or controlling person of the
Company) and any underwriters acting on behalf of the Company against all claims, losses, expenses, damages and liabilities (or actions in respect thereof) to which they may become subject under the Act or otherwise, arising out of or based upon any
untrue or alleged untrue statement filed pursuant hereto, or any document relating thereto, including all amendments, and supplements, or arising out of or based upon the omission or alleged omission to state therein a material fact required to be
stated therein or necessary to make the statements therein contained not misleading, and, will reimburse the Company (or such other aforementioned parties) or such underwriters for any legal and other expenses reasonably incurred in connection with
investigating or defending any such claim, loss, damage, liability, or action; provided, however, that the Holder will be liable as aforesaid only to the extent that such untrue or alleged untrue statement or omission or alleged omission is based
upon information furnished in writing to the Company by the Holder or any underwriter obtained by the Holder expressly for use therein, or as a result of its or such underwriter’s failure to furnish the Company with information duly requested
in writing by counsel for the Company specifically for use therein. This indemnity agreement contained in this paragraph (v) shall remain operative and in full force and effect regardless of any investigation made by or on behalf of any
indemnified party and shall survive the delivery of and payment for the Warrant Shares. 
 (vi) Promptly after receipt by an indemnified
party under this subsection 10.4 of notice of the commencement of any action, such indemnified party will, if a claim in respect thereof is to be made against the indemnifying party, promptly notify the indemnifying party of the commencement
thereof, but the omission so to notify the indemnifying party will not relieve it from any liability which it may have to any indemnified party otherwise than under this subsection 10.4. In case any such action is brought against any indemnified
party, and it notifies the indemnifying party of the commencement thereof, the indemnifying party will be entitled to participate in, and, to the extent that it may wish jointly with any other indemnifying party similarly notified, to assume the
defense thereof, with counsel reasonably satisfactory to such indemnified party, and after notice from the indemnifying party of its election so to assume the defense thereof, the indemnifying party will not be liable to such indemnified party under
this subsection 10.4 for any legal or other expenses subsequently incurred by such indemnified party in connection with the defense thereof, other than reasonable costs of investigation or out-of-pocket expenses or losses or cost incurred in
collaborating in the defense. 
 (vii) Except as set forth in subsection 10.4(viii), the Company shall bear all costs and expenses incident
to any registration pursuant to this Section 10. 
 (viii) The Holder shall pay any and all underwriters’ discounts, commissions,
brokerage fees and transfer taxes incident to the sale of any securities sold by such Holder pursuant to this Section 10, and shall pay the fees and expenses of any attorneys or accountants or other advisors retained by it. 
 10.5 Notwithstanding the foregoing, with respect to any demand made pursuant to Section 10.2, if the Company shall furnish to the Holder requesting
to exercise the demand 

  

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right set forth in Section 10.2 above a certificate signed by the president of the Company stating that in the good faith judgment of the Board of
Directors it would be seriously detrimental to the Company and its stockholders for such registration statement to be filed at the date filing would be required, and it is therefore essential to delay the filing of such registration statement, the
Company shall have an additional period of not more than ninety (90) days within which to file such registration statement; provided, however, that the Company may exercise its delay right under this paragraph no more than one (1) time.

  

	 	11	No Voting or Dividend Rights; Limitation of Liability 

 Nothing contained in this Warrant shall be construed as conferring on the Holder hereof the right to vote, to consent or to receive notice as a stockholder of the Company or any other matters or any rights whatsoever as a stockholder of the
Company. No dividends or interest shall be payable or accrued in respect of this Warrant or the interest represented hereby or the shares purchasable hereunder until, and only to the extent that, this Warrant is exercised. No provisions hereof, in
the absence of affirmative action by the Holder to purchase shares of Common Stock, and no mere enumeration herein of the rights or privileges of the Holder, shall give rise to any liability of such Holder for the Exercise Price or as a stockholder
of the Company, whether such liability is asserted by the Company or by its creditors. 
  

	 	12	Governing Law 

 This Warrant Certificate shall be
governed by and construed in accordance with the laws of the State of Delaware. 
  

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 IN WITNESS WHEREOF, the Company has caused this Warrant Certificate to be duly executed by its officers
thereunto duly authorized and its corporate seal to be affixed hereon, as of this              day of June, 2007. 
  

			
	drugstore.com, inc.
		
	 By:
	 	  

	 Name:
	 	  

	 Title:
	 	  



 [SEAL] 
  

			
	Attest:
	
	  

	 Name:
	 	  

	 Title:
	 	  


  

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 EXHIBIT A 
 NOTICE OF EXERCISE 
 The undersigned hereby irrevocably elects to exercise, pursuant to Section 2 of
the Warrant Certificate accompanying this Notice of Exercise,                      Warrants of the total number of Warrants owned by the
undersigned pursuant to the accompanying Warrant Certificate, and herewith makes payment of the Purchase Price of such shares in full. 
  

	
	  
 Name of Holder

	
	  
 Signature

	
	Address:
	  
  
  



  

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 EXHIBIT B 
 NOTICE OF CONVERSION 
 The undersigned hereby irrevocably elects to convert, pursuant to Section 7 of the Warrant
Certificate accompanying this Notice of Conversion,                      Warrants of the total number of Warrants owned by the undersigned
pursuant to the accompanying Warrant Certificate into shares of the Common Stock of the Company (the “Shares”). 
 The number of Shares to be
received by the undersigned shall be calculated in accordance with the provisions of Section 7.1 of the accompanying Warrant Certificate. 
  

	
	  
 Name of Holder

	
	  
 Signature

	
	Address:
	  
  
  



  

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