Document:

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                                                                    EXHIBIT 10.2

                              DRUGSTORE.COM, INC.
                              -------------------

                      PREFERRED STOCK PURCHASE AGREEMENT
                      ----------------------------------

     This Preferred Stock Purchase Agreement (this "Agreement") is made as of
                                                    ---------
July 30, 2000 by and among drugstore.com, inc., a Delaware corporation (the

"Company"), and the investors listed on Schedule I attached hereto (each a
--------
"Purchaser" and together the "Purchasers").
----------                    ----------

     The parties hereby agree as follows:

     1.   Purchase and Sale of Preferred Stock.
          ------------------------------------

          1.1  Sale and Issuance of Preferred Stock.
               ------------------------------------

               (a) Subject to the terms and conditions of this Agreement, each
of the Purchasers agrees to purchase and the Company agrees to sell and issue to
such Purchaser that number of shares of Series 1 Preferred Stock, par value
$0.0001, of the Company (the "Preferred Stock"), determined by dividing the
                              ---------------
Purchase Commitment listed opposite such Purchaser's name on Schedule 1 by
$493.75. The Company shall have the right to amend Schedule I hereto to add
additional Purchasers at any time prior to the Closing, and any such Purchasers
shall become parties to this Agreement.

               (b) The Preferred Stock shall have the rights and restrictions as
set forth in the Certificate of Designation of Series 1 Preferred Stock of
drugstore.com, inc. (the "Certificate of Designation") attached hereto as
                          --------------------------
Exhibit A.
---------

               (c) The parties hereto acknowledge that, concurrently herewith,
the Company is entering into a Common Stock Purchase Agreement with the several
purchasers listed on Schedule I thereto (the "Common Stock Purchase Agreement"),
                                              -------------------------------
pursuant to which such purchasers have agreed to purchase, subject to the terms
and conditions of the Common Stock Purchase Agreement, at least 8,101,265 shares
of Common Stock, par value $0.0001 per share, of the Company (the "Common
                                                                   ------
Stock"), having the rights and restrictions set forth in the Amended and
-----
Restated Certificate of Incorporation of drugstore.com, inc. attached hereto as
Exhibit B (the "Restated Certificate."). The Common Stock to be issued pursuant
---------       --------------------
to the Common Stock Purchase Agreement shall hereinafter be referred to as the

"Stock".
------

          1.2  Closing; Delivery.
               -----------------

               (a) The purchase and sale of the Preferred Stock shall take place
at the offices of Simpson Thacher & Bartlett (or such other location mutually
agreeable to the parties hereto) no later than 5 business days after the
satisfaction or (subject to applicable law) waiver of the conditions set forth
in Sections 4 and 5 (excluding conditions that, by their terms, cannot be
satisfied until the Closing) (which time and place are designated as the
"Closing").
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               (b) At the Closing, the Company shall deliver to each Purchaser a
certificate or certificates for the number of shares of the Preferred Stock to
be purchased by such Purchaser pursuant to this Agreement against delivery of
the consideration therefor, by wire transfer of immediately available funds to
the Company's bank account.

     2.   Representations and Warranties of the Company.  The Company hereby
          ---------------------------------------------
represents and warrants to each Purchaser that:

          2.1  Good Standing.  Each of Company and its Subsidiaries (i) is a
               -------------
corporation duly organized, validly existing and in good standing under the laws
of its state of incorporation; (ii) has the power and authority to own, lease
and operate its properties and carry on its business as now conducted; and (iii)
is duly qualified, licensed to do business and in good standing as a foreign
corporation in each jurisdiction where the failure to be so qualified could
reasonably be expected to have a material adverse effect on the business,
assets, operations or financial condition of the Company ("Material Adverse
                                                           ----------------
Effect").
------

          2.2  Capitalization.
               --------------

               (a) The authorized capital of the Company consists of 250,000,000
shares of Common Stock and 10,000,000 shares of Preferred Stock, $0.0001 per
share (the "Preferred Stock"). The Common Stock has the rights, preferences and
            ---------------
privileges set forth in the Company's Restated Certificate, and the Preferred
Stock has the rights, preferences and privileges set forth in the Certificate of
Designations

               (b) As of the date of this Agreement, 52,962,714 shares of Common
Stock and no shares of Preferred Stock are issued and outstanding. All of the
outstanding shares of Common Stock have been, and when issued and paid for in
accordance with the terms of the Common Stock Purchase Agreement the Stock will
be, validly issued, duly authorized, fully paid and nonassessable, and issued in
compliance with all applicable federal and state securities laws (based in part
upon the representations of the purchasers thereof contained in the Common Stock
Purchase Agreement). All of the shares of Series 1 Preferred Stock, when issued
and paid for in accordance with the terms of this Agreement, will be validly
issued, duly authorized, fully paid and nonassessable, and issued in compliance
with all applicable federal and state securities laws (based in part upon the
representations of the Purchasers contained in Sections 3.4, 3.5, 3.6, 3.7 and
3.8).

               (c) As of the date of this Agreement (i) 17,509,148 shares of
Common Stock are reserved for issuance under the Company's 1998 Stock Plan (of
which 8,000 shares have been issued pursuant to restricted stock agreements,
890,839 shares are issuable under outstanding options that are currently
exercisable, 10,367,423 shares are issuable under other outstanding options that
are not currently exercisable and 6,250,886 shares remain available for future
grants), (ii) 32,404 shares of Common Stock are reserved for issuance under the
Company's Beauty.com Inc. Stock Plan (of which 9,606 shares are issuable under
outstanding options, all of which are currently exercisable and 22,798 remain
available for future grants) and (iii) 1,000,000 shares of Common Stock are
reserved for issuance under the Company's 1999 Employee Stock Purchase Plan (of
which 87,719 have been issued to date).

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               (d) Except for the conversion privileges of the Preferred Stock
and except as set forth in (i) the warrant to purchase 500,000 shares of Common
Stock issued on June 26, 2000 to Tel-Drug, Inc. (the "Tel-Drug Warrant") and
                                                      ----------------
(ii) the warrant to purchase 2,500,000 shares of Common Stock issued on July 30,
2000 to Amazon.com, Inc. (the "Amazon Warrant"), as of the date of this
                               --------------
Agreement there are no outstanding options, warrants, rights (including
conversion or preemptive rights and rights of first refusal or similar rights)
or agreements, oral or in writing, for the purchase or acquisition from the
Company of any shares of its capital stock.

               (e) The Company's only subsidiaries are DS Pharmacy, Inc., DS
Non-Pharmaceutical Sales, Inc., DS Distribution, Inc., DSGC Idaho, Inc.,
Beauty.com, Inc. and Beauty.com Sales, Inc. (each a "Subsidiary" and together,
the "Subsidiaries").

          2.3  Authorization.  All corporate action on the part of the Company,
               -------------
its officers, directors and stockholders necessary for the authorization,
execution and delivery of this Agreement and the Common Stock Purchase Agreement
(collectively, the "Agreements") and the performance of all obligations of the
                    ----------
Company hereunder and thereunder and the authorization, issuance and delivery of
the Stock and the Preferred Stock has been taken or will be taken prior to the
Closing (subject, in the case of the conversion of the Preferred Stock into
Common Stock, to the receipt of the Stockholder Approval (as defined herein)),
and the Agreements, when executed and delivered by the Company, will constitute
valid and legally binding obligations of the Company, enforceable against the
Company in accordance with their terms except as limited by applicable
bankruptcy, insolvency, reorganization, moratorium, fraudulent conveyance, and
other laws of general application affecting enforcement of creditors' rights
generally, as limited by laws relating to the availability of specific
performance, injunctive relief, or other equitable remedies, and except as may
be limited by Section 6.2(c).

          2.4  Valid Issuance of Preferred Stock.  The Preferred Stock that will
               ---------------------------------
be issued to the Purchasers at Closing will have been duly and validly reserved
for issuance and, when issued and delivered in accordance with the terms hereof,
will be duly authorized, validly issued, fully paid and nonassessable and free
of restrictions on transfer other than restrictions on transfer under this
Agreement and applicable state and federal securities laws.  Based in part upon
the representations of the Purchasers in this Agreement, the Preferred Stock
will be issued in compliance with all applicable federal and state securities
laws.  The Common Stock issuable upon conversion of the Preferred Stock has been
duly and validly reserved for issuance, and upon issuance in accordance with the
terms of the Certificate of Designations, will be duly authorized, validly
issued, fully paid and nonassessable and free of restrictions on transfer other
than restrictions on transfer under this Agreement and applicable federal and
state securities laws and will be issued in compliance with all applicable
federal and state securities laws.

          2.5  Litigation.  There is no action, suit, proceeding or
               ----------
investigation pending or, to the Company's knowledge, currently threatened
against the Company or any of its subsidiaries that (i) questions the validity
of the Agreements or the right of the Company or any of its subsidiaries, as
applicable, to enter into them, or to consummate the transactions

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contemplated hereby or thereby nor is the Company aware that there is any basis
for the foregoing or (ii) if adversely determined would have a Material Adverse
Effect. Neither the Company nor any of its subsidiaries is a party or subject to
the provisions of any order, writ, injunction, judgment or decree of any court
or government agency or instrumentality that (i) challenges the validity of the
Agreements or the right of the Company or any of its subsidiaries, as
applicable, to enter into this Agreement, or to consummate the transactions
contemplated hereby and thereby or (ii) would have a Material Adverse Effect.

          2.6   Liabilities. The Company and its subsidiaries, on a consolidated
                -----------
basis, have no liabilities and there are no contingent liabilities, required by
generally accepted accounting principles to be disclosed on a balance sheet but
that are not disclosed on the Company's audited balance sheet as of January 2,
2000 and/or on the Company's unaudited balance sheet as of July 2, 2000 except
liabilities that would not have a Material Adverse Effect. Subsequent to July 2,
2000, the Company and its subsidiaries, on a consolidated basis, have not
incurred any liabilities or any contingent liabilities required by generally
accepted accounting principles to be disclosed on the Company's balance sheet
except liabilities that would not have a Material Adverse Effect.

          2.7   Compliance with Other Instruments. The execution, delivery and
                ---------------------------------
performance of the Agreements and the consummation of the transactions
contemplated hereby and thereby will not result in any violation or be in
conflict with or constitute, with or without the passage of time and giving of
notice, either a default under or cause acceleration under any provision of the
Restated Certificate or the bylaws of the Company or any instrument, judgment,
order, writ, decree or contract to which the Company or any of its Subsidiaries
is a party or by which it is bound, or any provision of any federal or state
statute, rule or regulation applicable to the Company or any of its
Subsidiaries, the effect of which would (i) have a Material Adverse Effect, (ii)
materially and adversely affect the ability of the Company and its Subsidiaries
to perform their respective obligations under the Agreements or (iii) result in
the creation of any material lien, charge or encumbrance upon any assets of the
Company or any of its Subsidiaries.

          2.8   Material Agreements.  The Company has filed with the SEC all
                -------------------
agreements in existence as of the date of this Agreement that (a) define or
affect the rights of security holders of the Company in their capacity as
security holders including, but not limited to, such security holders' voting
rights, registration rights or standstill rights or obligations, other than (i)
the Agreement dated June 23, 2000 between the Company and WellPoint Health
Networks Inc., (ii) the Tel-Drug Warrant and (iii) the Amazon Warrant or (b) are
required to be filed under Item 601 of Regulation S-K.

          2.9.  Financial Statements.  The financial statements of Company that
                --------------------
have been delivered to the Investors (including those for the period ended July
2, 2000), (i) are in accordance with the books and records of Company and its
Subsidiaries, which have been maintained in accordance with good business
practice; (ii) have been prepared in conformity with GAAP (except as discussed
therein, the absence of footnotes for all unaudited periods and, in the case of
audited financial statements, as approved by the relevant firm of accountants);
and (iii) fairly present the consolidated financial position of Company as of
the dates presented

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therein and the results of operations, changes in financial positions or cash
flows, as the case may be, for the periods presented therein (except, in the
case of financial statements for the period ended July 2, 2000, for normal year-
end audit adjustments). None of the Company or any of the Company's Subsidiaries
has any contingent obligations, liability for taxes or other outstanding
obligations that are material in the aggregate, except as disclosed in the
unaudited financial statements for the period ended July 2, 2000 (except for
normal year-end audit adjustments). None of the Company or its Subsidiaries has
any contingent obligations or liability for taxes that are material in the
aggregate and that would be required to be reflected or reserved against in the
latest balance sheet of the Company, except as disclosed in the unaudited
financial statements for the period ended July 2, 2000 (except for normal year-
end audit adjustments).

          2.10. Investment Company.  None of Company or its Subsidiaries is
                ------------------
subject to regulation under the Investment Company Act of 1940, or to any
federal or state statute or regulation limiting its ability to incur
indebtedness.

          2.11. SEC Reporting; Information Provided.  As of the date each was
                -----------------------------------
filed, none of the Company's registration statements, reports or other filings
made with the Securities and Exchange Commission, contained any untrue statement
of a material fact or omitted to state a material fact necessary to make the
statements therein, in light of the circumstances under which they were made,
not misleading.  Neither this agreement nor any document, certificate or
instrument furnished to any of the Purchasers by or on behalf of the Company
when taken in conjunction with any supplemental or revised information furnished
to any of the Purchasers in writing prior to the date hereof contains any untrue
statement of a material fact or omits, or will omit, to state a material fact
necessary to make the statements in such documents, certificates, instruments or
other information provided, in light of the circumstances in which they were
made, not misleading, except that with respect to any projected financial
information, the Company only represents that it was prepared in good faith and
the Company reasonably believes that the assumptions made in preparing such
projections were reasonable as of the date of such projections.

          2.12. Absence of Certain Changes.  Since July 2, 2000, no event has
                --------------------------
occurred and no condition exists which would have a Material Adverse Effect,
other than (i) any change in the price of the Common Stock or (ii) changes in
general economic conditions or conditions affecting the Company's industry
generally.

          2.13. Real Property Holding Company.   The Company is not, and has
                -----------------------------
not been, a "United States real property holding corporation" within the meaning
of Section 897(c)(2) of the Internal Revenue Code of 1986, as amended (the

"Code"), during the applicable period described in Section 897(c)(1)(A)(ii) of
 ----
the Code.

          2.14  Form S-3 Eligibility.  The Company and the transactions
                ---------------------
contemplated by Section 6.2 of this Agreement meet the requirements for using
Form S-3 under the Securities Act for resale.

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     3.   Representations and Warranties of the Purchasers.  Each Purchaser
          ------------------------------------------------
hereby represents and warrants to the Company with respect to itself that:

          3.1   Authorization. Such Purchaser has full power and authority to
                -------------
enter into and deliver this Agreement, and this Agreement, when executed and
delivered by the Purchaser, will constitute a valid and legally binding
obligation of the Purchaser, enforceable against the Purchaser in accordance
with its terms except as limited by applicable bankruptcy, insolvency,
reorganization, moratorium, fraudulent conveyance, and other laws of general
application affecting enforcement of creditors' rights generally, as limited by
laws relating to the availability of specific performance, injunctive relief, or
other equitable remedies, and except as may be limited by Section 6.2(c)..

          3.2   Litigation.  There is no action, suit, proceeding or
                ----------
investigation pending or, to the Purchaser's knowledge, currently threatened
against the Purchaser or any of its subsidiaries that questions the validity of
this Agreement or the right of the Purchaser or any of its subsidiaries, as
applicable, to enter into this Agreement, or to consummate the transactions
contemplated hereby nor is the Purchaser aware that there is any basis for the
foregoing.  Neither the Purchaser nor any of its subsidiaries is a party or
subject to the provisions of any order, writ, injunction, judgment or decree of
any court or government agency or instrumentality that challenges the validity
of this Agreement or the right of the Purchaser or any of its subsidiaries, as
applicable, to enter into this Agreement, or to consummate the transactions
contemplated hereby.

          3.3   Compliance with Other Instruments. The execution, delivery and
                ---------------------------------
performance of this Agreement and the consummation of the transactions
contemplated hereby will not result in any violation or be in conflict with or
constitute, with or without the passage of time and giving of notice, either a
default under any provision of the governing documents of the Purchaser or any
instrument, judgment, order, writ, decree or contract to which the Purchaser or
any of its subsidiaries is a party or by which it is bound, or any provision of
any federal or state statute, rule or regulation applicable to the Purchaser or
any of its subsidiaries, the effect of which would have a material adverse
effect on the ability of the Purchaser and its subsidiaries to perform their
respective obligations under this Agreement or result in the creation of any
lien, charge or encumbrance upon any assets of the Purchaser or any of its
subsidiaries.

          3.4   Purchase Entirely for Own Account.  This Agreement is made with
                ---------------------------------
the Purchaser in reliance upon the Purchaser's representation to the Company,
which by the Purchaser's execution of this Agreement, the Purchaser hereby
confirms, that the Preferred Stock to be acquired by the Purchaser will be
acquired for investment for the Purchaser's own account, not as a nominee or
agent, and not with a view to the resale or public distribution of any part
thereof in violation of any requirements of the Securities Act of 1933, as
amended (the "Securities Act") or applicable state securities laws.  The
              --------------
Purchaser has no present intention of selling, granting any participation in, or
otherwise distributing any Preferred Stock purchased hereunder, including,
without limitation, entering into any arrangement that transfers to another, in
whole or in part, any of the economic consequences of ownership of the Stock,
whether any such transaction is to be settled by delivery of Preferred Stock,
Common Stock or

                                                                               6
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other securities, in cash or otherwise. By executing this Agreement, the
Purchaser further represents that the Purchaser does not presently have any
contract, undertaking, agreement or arrangement with any person to sell,
transfer or grant participation to such person or to any third person, with
respect to any of the Preferred Stock or the Common Stock issuable upon
conversion thereof.

          3.5   Disclosure of Information.  The Purchaser (i) has had an
                -------------------------
opportunity to discuss the Company's business, management, financial affairs and
the terms and conditions of the offering of the Preferred Stock with the
Company's management and (ii) has had an opportunity to review the Company's
facilities.  The Purchaser understands that such discussions and reviews, as
well as any written information delivered by the Company to the Purchaser, were
intended to describe the aspects of the Company's business that it believes to
be material.

          3.6   Restricted Securities.  The Purchaser understands that the
                ---------------------
Preferred Stock has not been, and will not be, registered under the Securities
Act, by reason of a specific exemption from the registration provisions of the
Securities Act that depends upon, among other things, the bona fide nature of
the investment intent and the accuracy of the Purchaser's representations as
expressed herein.  The Purchaser understands that the shares of Preferred Stock
are "restricted securities" under applicable U.S. federal and state securities
laws and that, pursuant to these laws, the Purchaser must hold the shares of
Preferred Stock indefinitely unless they are registered with the Securities and
Exchange Commission and qualified by state authorities, or an exemption from
such registration and qualification requirements is available.  The Purchaser
acknowledges that the Company has no obligation to register or qualify the
Preferred Stock for resale except with regards to the Common Stock issuable upon
conversion of the Preferred Stock as set forth in Section 6.2 hereof.  The
Purchaser further acknowledges that if an exemption from registration or
qualification is available, it may be conditioned on various requirements
including, but not limited to, the time and manner of sale, the holding period
for the Preferred Stock, and on requirements relating to the Company that are
outside of the Purchaser's control, and that the Company is under no obligation,
and may not be able, to satisfy.

          3.7   Legends. The Purchaser understands that the Preferred Stock, and
                -------
any securities issued in respect thereof, may bear one or all of the following
legends:

               (a) "THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AND HAVE BEEN ACQUIRED FOR
INVESTMENT AND NOT WITH A VIEW TO, OR IN CONNECTION WITH, THE SALE OR
DISTRIBUTION THEREOF.  NO SUCH SALE OR DISTRIBUTION MAY BE EFFECTED WITHOUT AN
EFFECTIVE REGISTRATION STATEMENT RELATED THERETO OR AN OPINION OF COUNSEL IN A
FORM SATISFACTORY TO THE COMPANY THAT SUCH REGISTRATION IS NOT REQUIRED UNDER
THE SECURITIES ACT OF 1933."

               (b) Any legend required by the "Blue Sky" laws of any state to
the extent such laws are applicable to the shares represented by the certificate
so legended.

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          3.8   Accredited Investor.  The Purchaser is an accredited investor as
                -------------------
defined in Rule 501(a) of Regulation D promulgated under the Securities Act.

     4.   Conditions of the Purchasers' Obligations at Closing.  The obligations
          ----------------------------------------------------
of the Purchasers to the Company under this Agreement are subject to the
fulfillment, on or before the Closing, of each of the following conditions,
unless otherwise waived by each Purchaser:

          4.1   Representations and Warranties.  The representations and
                ------------------------------
warranties of the Company shall be true and correct on and as of the date of the
Closing with the same effect as though such representations and warranties had
been made on and as of the date of the Closing (except with respect to the
representations and warranties contained in Section 2.2(b), 2.2(c) and the first
sentence of Section 2.2(e), which shall be true and correct in all material
respects as of the date of the Closing).

          4.2   Performance.  The Company shall have performed and complied with
                -----------
all covenants, agreements, obligations and conditions contained in this
Agreement that are required to be performed or complied with by it on or before
the Closing and the Company shall have obtained any and all consents, permits
and waivers necessary or appropriate for consummation of the transactions
contemplated by the Agreements.

          4.3   Reservation of Shares.  The Preferred Stock issuable pursuant to
                ---------------------
this Agreement shall have been duly authorized and reserved for issuance at the
Closing.  The Common Stock issuable upon conversion of the Preferred Stock
pursuant to the Certificate of Designations shall have been duly authorized and
reserved for issuance at the Closing.

          4.4   Compliance Certificate.  The President of the Company shall
                ----------------------
deliver to the Purchasers at the Closing a certificate certifying that the
conditions specified in Sections 4.1, 4.2 and 4.3 have been fulfilled.

          4.5   Qualifications.  All authorizations, approvals or permits, if
                --------------
any, of any governmental authority or regulatory body of the United States or of
any state that are required in connection with the lawful issuance and sale of
the Preferred Stock pursuant to this Agreement shall be obtained and effective
as of the Closing including, without limitation, the expiration or termination
of all waiting periods under the Hart-Scott-Rodino Antitrust Improvement Act of
1976, as amended (the "HSR Act").
                       -------

          4.6   Opinion of Company Counsel.  The Purchasers at the Closing shall
                --------------------------
have received from Simpson Thacher & Bartlett, counsel for the Company, an
opinion dated as of the Closing covering the matters set forth on Exhibit C.
                                                                  ---------

          4.7   Common Stock Purchase Agreement.  The Company and the
                -------------------------------
purchasers parties thereto shall have executed and delivered the Common Stock
Purchase Agreement covering the purchase of at least 8,101,265 shares of Common
Stock.

          4.8   Delivery of Voting Agreements.  Each person listed on Exhibit
                -----------------------------                         -------
D hereto shall have executed and delivered to the Purchasers a voting agreement
-
in the form attached hereto an Exhibit E (each, a "Voting Agreement") to the
                               ---------           ----------------
effect that such person will

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<PAGE>

vote its shares of Common Stock at the Stockholder
Meeting (as defined) in favor of the approval of the issuance of the Common
Stock issuable upon conversion of the Preferred Stock.  The persons delivering
Voting Agreements shall represent a majority of the Common Stock.

          4.9.  Minimum Investment at Closing.  At the Closing, Purchasers
                -----------------------------
investing at least $62,682,825 in the aggregate in the Company under the
Agreements shall have wired their respective investments in the Company into an
escrow account maintained by Brobeck, Phleger & Harrison or an escrow agent
mutually agreeable to the Company and purchasers of the majority of the
Preferred Stock for delivery to the Company, or shall be otherwise legally
obligated to wire such amounts to the Company, before any Purchaser is obligated
to close.

          4.10. Opinion of General Counsel to the Company.   The Purchasers at
                -----------------------------------------
the Closing shall have received from the General Counsel of the Company an
opinion dated as of the Closing covering the matters set forth on Exhibit F.
                                                                  ---------

     5.   Conditions of the Company's Obligations at Closing.  The obligations
          --------------------------------------------------
of the Company to the Purchasers under this Agreement are subject to the
fulfillment, on or before the Closing, of each of the following conditions,
unless otherwise waived:

          5.1   Representations and Warranties.  The representations and
                ------------------------------
warranties of the Purchasers contained in Section 3 shall be true and correct in
all material respects on and as of the date of the Closing with the same effect
as though such representations and warranties had been made on and as of the
date of the Closing (except to the extent such representations and warranties
speak as of the date of this Agreement, in which case they shall be true and
correct in all material respects on and as of the date of this Agreement).

          5.2   Performance.  All covenants, agreements and conditions contained
                -----------
in this Agreement to be performed by the Purchasers on or prior to the Closing
shall have been performed or complied with in all material respects.

          5.3   Compliance Certificate.  A senior executive officer of each of
                ----------------------
the Purchasers shall deliver to the Company at the Closing a certificate
certifying that the conditions specified in Sections 5.1 and 5.2 have been
fulfilled.

          5.4   Qualifications.  All authorizations, approvals or permits, if
                --------------
any, of any governmental authority or regulatory body of the United States or of
any state that are required in connection with the lawful issuance and sale of
the Preferred Stock pursuant to this Agreement shall be obtained and effective
as of the Closing including, without limitation, the expiration or termination
of all waiting periods under the HSR Act.

          5.5   Common Stock Purchase Agreement.  The Company and the purchasers
                -------------------------------
parties thereto shall have executed and delivered the Common Stock Purchase
Agreement covering the purchase of at least 8,101,265 shares of Common Stock.

                                                                               9
<PAGE>

          5.6   Delivery of Voting Agreements.  Each person listed on Exhibit D
                -----------------------------                         ---------
hereto shall have executed and delivered to the Purchasers a Voting Agreement.
The persons delivering Voting Agreements shall represent a majority of the
Common Stock.

     6.   Covenants.
          ---------

          6.1   HSR Act Filings.  As soon as practicable after the execution of
                ---------------
this Agreement, the Company and each relevant Purchaser will separately file
with the Antitrust Division of the United States Department of Justice and the
United States Federal Trade Commission pursuant to the HSR Act all requisite
documents and notifications in order to provide for the issuance and sale of the
Preferred Stock pursuant to this Agreement.  The parties will cooperate and
coordinate with one another in exchanging information and providing reasonable
assistance as the other party may request in connection with the foregoing.

          6.2   Registration Rights. (a) The Company hereby agrees: (i) to use
                -------------------
its best efforts to file a resale shelf registration statement (the
"Registration Statement") under the Securities Act as soon as reasonably
 ----------------------
practicable covering resales of the Common Stock to be issued upon conversion of
the Preferred Stock (such shares of Common Stock, the "Conversion Stock") by the
                                                       ----------------
Purchasers and the Stock to be issued pursuant to the Common Stock Purchase
Agreement, (ii) to use its best efforts to cause the Registration Statement to
be declared effective as soon as reasonably practicable but in any event within
60 days of Closing and (iii) to maintain the effectiveness of the Registration
Statement until the earlier of (x) the eighteen month anniversary of the
effective date of the Registration Statement and (y) the date on which all
shares of Conversion Stock have been resold by the Purchasers.  At any time when
the Registration Statement is effective, the Board of Directors of the Company
may determine, as indicated in a certificate signed by any Director of the
Company, the Chief Financial Officer of the Company or the Secretary of the
Company, to suspend offers and sales by Purchasers under the Registration
Statement if an event has occurred or is reasonably likely to occur that would
require additional disclosure by the Company and that the Company has a bona
fide business purpose for keeping confidential, and the nondisclosure of which
would reasonably be expected to cause the Registration Statement to fail to
comply with applicable disclosure requirements.  The Company shall give the
Purchasers written notice of the Board of Directors' determination and the
Purchasers agree to suspend offers and sales under the Registration Statement
until the Company has delivered a subsequent notice to the Purchasers revoking
its prior notice; provided, however, that the eighteen month period during which
                  --------  -------
the Registration Statement is required to be effective shall be extended by the
number of days of such suspensions.  The Company may not revoke the ability of
Purchasers to make offers and sales under the Registration Statement more than
three times or for more than 90 days in the aggregate.

     (b)  For the period during which the Registration Statement is effective,
the Company shall:

          (i)   furnish to the Purchaser with respect to the Conversion Stock
     registered under the Registration Statement (and to each underwriter, if
     any, of such Conversion  Stock) such reasonable number of copies of
     prospectuses in order to facilitate the

                                                                              10
<PAGE>

     public sale or other disposition of all or any of the Conversion Stock by
     the Purchaser; provided, however, that the obligation of the Company to
                    --------  -------
     deliver copies of prospectuses to the Purchaser shall be subject to the
     receipt by the Company of reasonable assurances from the Purchaser that the
     Purchaser will comply with the applicable provisions of the Securities Act
     and of such other securities or blue sky laws as may be applicable in
     connection with any use of such prospectuses;

          (ii)  during the period when such prospectuses are required to be
      delivered under the Securities Act or the Securities Exchange Act of 1934,
      as amended (the "Exchange Act"), file all documents required to be filed
                       ------------
      with the Commission pursuant to Section 13, 14 or 15 of the Exchange Act
      within the time periods required by the Exchange Act and the rules and
      regulations promulgated thereunder;

          (iii) file documents required of the Company for normal blue sky
      clearance in states specified in writing by the Purchaser; provided,
                                                                 --------
      however, that the Company shall not be required to qualify to do business
      -------
      or consent to service of process in any jurisdiction in which it is not
      now so qualified or has not so consented;

          (iv)  authorize for listing on the Nasdaq National Market the shares
      of Conversion Stock by filing with the Nasdaq National Market a
      Notification of Listing of Additional Shares (or such other form, if any,
      as may be required by the Nasdaq National Market) as soon as reasonably
      practicable after the filing of the Registration Statement or otherwise in
      accordance with the rules and regulations of the Nasdaq National Market;
      and

          (v)   bear all expenses in connection with the procedures in this
      Section 6.2 and the registration of the Conversion Stock pursuant to the
      Registration Statement, other than fees and expenses, if any, of counsel
      or other advisers to the Purchaser or underwriting discounts, brokerage
      fees and commissions incurred by the Purchaser, if any.

     (c)  For purposes of this Section 6.2(c), the term "Registration Statement"
                                                         ----------------------
shall include any preliminary or final prospectus, exhibit, supplement or
amendment included in or relating to the Registration Statement referred to in
Section 6.2(a).

          (i)   The Company agrees to indemnify and hold harmless each of the
     Purchasers and each of their respective directors, officers, members and
     partners, and each person, if any, who controls any Purchaser within the
     meaning of the Securities Act, against any losses, claims, damages,
     liabilities or expenses, joint or several, to which such Purchasers and
     each of their respective directors, officers, members and partners, or such
     controlling person may become subject, under the Securities Act, the
     Exchange Act, or any other federal or state statutory law or regulation, or
     at common law or otherwise (including in settlement of any litigation, if
     such settlement is effected with the written consent of the Company),
     insofar as such losses, claims, damages, liabilities or expenses (or
     actions in respect thereof as contemplated below) arise out of or are based
     upon any untrue statement or alleged untrue statement of any material fact
     contained in or incorporated by reference in the Registration Statement,
     including the

                                                                              11
<PAGE>

     prospectus, financial statements and schedules, and all other documents
     filed as a part thereof, as amended at the time of effectiveness of the
     Registration Statement, including the preliminary or final prospectus any
     information deemed to be a part thereof as of the time of effectiveness
     pursuant to paragraph (b) of Rule 430A, or pursuant to Rule 434, of the
     rules and regulations of the Commission under the Securities Act
     (the "Regulations"), or the prospectus, in the form first filed with
           -----------
     the Commission pursuant to Rule 424(b) of the Regulations, or filed as part
     of the Registration Statement at the time of effectiveness if no Rule
     424(b) filing is required (the "Prospectus"), or any amendment or
                                     ----------
     supplement thereto, or arise out of or are based upon the omission or
     alleged omission to state in any of them a material fact required to be
     stated therein or necessary to make the statements in any of them, in light
     of the circumstances under which they were made, not misleading, or arise
     out of or are based in whole or in part on any failure of the Company to
     perform its obligations under or a violation of the Securities Act, the
     Exchange Act or any state securities law, and will reimburse each Purchaser
     and each of their respective directors, officers, members and partners, and
     each such controlling person for any legal and other expenses as such
     expenses are reasonably incurred by such Purchaser or such controlling
     person in connection with investigating, defending, settling, compromising
     or paying any such loss, claim, damage, liability, expense or action;

     provided, however, that the Company will not be liable in any such case to
     --------  -------
     the extent that any such loss, claim, damage, liability or expense arises
     out of or is based upon (i) an untrue statement or alleged untrue statement
     or omission or alleged omission made in the Registration Statement, the
     Prospectus or any amendment or supplement thereto in reliance upon and in
     conformity with written information furnished to the Company by or on
     behalf of the Purchaser expressly for use therein, or (ii) the failure of
     such Purchaser to comply with the covenants and agreements contained in
     this Section 6.2 respecting the sale of the Stock, or (iii) any statement
     or omission in any Prospectus that is corrected in any subsequent
     Prospectus that was delivered to the Purchaser prior to the pertinent sale
     or sales by the Purchaser.

          (ii)  Each Purchaser will severally indemnify and hold harmless the
     Company, each of its directors, each of its officers who signed the
     Registration Statement and each person, if any, who controls the Company
     within the meaning of the Securities Act, against any losses, claims,
     damages, liabilities or expenses to which the Company, each of its
     directors, each of its officers who signed the Registration Statement or
     controlling person may become subject, under the Securities Act, the
     Exchange Act, or any other federal or state statutory law or regulation, or
     at common law or otherwise (including in settlement of any litigation, if
     such settlement is effected with the written consent of such Purchaser)
     insofar as such losses, claims, damages, liabilities or expenses (or
     actions in respect thereof as contemplated below) arise out of or are based
     upon any untrue or alleged untrue statement of any material fact contained
     in the Registration Statement, including the prospectus, financial
     statements and schedules, and all other documents filed as a part thereof,
     as amended at the time of effectiveness of the Registration Statement,
     including any information deemed to be a part thereof as of the time of
     effectiveness pursuant to paragraph (b) of Rule 430A, or pursuant to Rule
     434, of the Regulations, or the Prospectus, or any amendment or

                                                                              12
<PAGE>

     supplement thereto, or arise out of or are based upon the omission or
     alleged omission to state therein a material fact required to be stated
     therein or necessary to make the statements in any of them, in light of the
     circumstances under which they were made, not misleading, or arise out of
     or are based in whole or in part on any failure of such Purchaser to
     perform its obligations under the Securities Act, the Exchange Act or any
     state securities law, and will reimburse the Company, each of its
     directors, each of its officers who signed the Registration Statement and
     each such controlling person for any legal and other expenses as such
     expenses are reasonably incurred by such Purchaser or such controlling
     person in connection with investigating, defending, settling, compromising
     or paying any such loss, claim, damage, liability, expense or action, in
     each case to the extent, but only to the extent, that such untrue statement
     or alleged untrue statement or omission or alleged omission was made in the
     Registration Statement, the Prospectus, or any amendment or supplement
     thereto, in reliance upon and in conformity with written information
     furnished to the Company by or on behalf of any Purchaser expressly for use
     therein.

          (iii) Promptly after receipt by an indemnified party under this
     Section 6.2(c) of notice of the threat or commencement of any action, such
     indemnified party will, if a claim in respect thereof is to be made against
     an indemnifying party under this Section 6.2(c) promptly notify the
     indemnifying party in writing 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 for contribution or otherwise than under the
     indemnity agreement contained in this Section 6.2(c) or to the extent it is
     not prejudiced as a result of such failure.  In case any such action is
     brought against any indemnified party and such indemnified party seeks or
     intends to seek indemnity from an indemnifying party, the indemnifying
     party will be entitled to participate in, and, to the extent that it may
     wish, jointly with all other indemnifying parties similarly notified, to
     assume the defense thereof with counsel reasonably satisfactory to such
     indemnified party; provided, however, if the defendants in any such action
     include both the indemnified party and the indemnifying party and the
     indemnified party shall have reasonably concluded that there may be a
     conflict between the positions of the indemnifying party and the
     indemnified party in conducting the defense of any such action or that
     there may be legal defenses available to it and/or other indemnified
     parties which are different from or additional to those available to the
     indemnifying party, the indemnified party or parties shall have the right
     to select separate counsel to assume such legal defenses and to otherwise
     participate in the defense of such action on behalf of such indemnified
     party or parties.  Upon receipt of notice from the indemnifying party to
     such indemnified party of its election so to assume the defense of such
     action and approval by the indemnified party of counsel, the indemnifying
     party will not be liable to such indemnified party under this Section
     6.2(c) for any legal or other expenses subsequently incurred by such
     indemnified party in connection with the defense thereof unless (i) the
     indemnified party shall have employed such counsel in connection with the
     assumption of legal defenses in accordance with the proviso to the
     preceding sentence (it being understood, however, that the indemnifying
     party shall not be liable for the expenses of more than one separate
     counsel, approved by such indemnifying party, representing all of the
     indemnified parties who are parties to such action) or (ii) the
     indemnifying party

                                                                              13
<PAGE>

     shall not have employed counsel reasonably satisfactory to the indemnified
     party to represent the indemnified party within a reasonable time after
     notice of commencement of action, in each of which cases the reasonable
     fees and expenses of counsel shall be at the expense of the indemnifying
     party.

          (iv)  If the indemnification provided for in this Section 6.2 is
     required by its terms but is for any reason held to be unavailable to or
     otherwise insufficient to hold harmless an indemnified party under
     paragraphs (i), (ii) or (iii) of this Section 6.2(c) in respect to any
     losses, claims, damages, liabilities or expenses referred to herein, then
     each applicable indemnifying party shall contribute to the amount paid or
     payable by such indemnified party as a result of any losses, claims,
     damages, liabilities or expenses referred to herein in such proportion as
     is appropriate to reflect the relative fault of the indemnifying party on
     the one hand and the indemnified party on the other in connection with the
     statements or omissions that resulted in such loss, claim, damage,
     liability or expense as well as any other relevant equitable
     considerations.  The relative fault of the Company and such Purchaser shall
     be determined by reference to, among other things, whether the untrue or
     alleged statement of a material fact or the omission or alleged omission to
     state a material fact relates to information supplied by the Company or by
     such Purchaser and the parties' relative intent, knowledge, access to
     information and opportunity to correct or prevent such statement or
     omission.  The amount paid or payable by a party as a result of the losses,
     claims, damages, liabilities and expenses referred to above shall be deemed
     to include, subject to the limitations set forth in paragraph (iii) of this
     Section 6.2(c), any legal or other fees or expenses reasonably incurred by
     such party in connection with investigating or defending any action or
     claim.  The provisions set forth in paragraph (iii) of this Section 6.2(c)
     with respect to the notice of the threat or commencement of any threat or
     action shall apply if a claim for contribution is to be made under this
     paragraph (iv); provided, however, that no additional notice shall be
                     -------- --------
     required with respect to any threat or action for which notice has been
     given under paragraph (iii) for purposes of indemnification.
     Notwithstanding the provisions of this Section 6.2(c)(iv), no Purchaser
     shall be required to contribute any amount in excess of the net proceeds of
     the offering received by such Purchaser, except in the case of willful
     fraud by such Purchaser.  No person guilty of fraudulent misrepresentation
     (within the meaning of Section 11(f) of the Securities Act) shall be
     entitled to contribution from any person who was not guilty of such
     fraudulent misrepresentation.  The Purchasers' obligations to contribute
     pursuant to this Section 6.2(c)(iv) are several and not joint.

          6.3   Stockholder Meeting.  The Company shall cause (i) a special
                -------------------
meeting of its common stockholders (the "Stockholder Meeting") to be held as
                                         -------------------
soon as practicable but in no event later than three months from the Closing,
for the purpose of approving the conversion of the Preferred Stock issued
pursuant to this Agreement into Common Stock or (ii) the holders of the
requisite number of shares of Common Stock to deliver written consents approving
the conversion of the Preferred Stock into Common Stock (the action called for
in (i) and (ii), the "Stockholder Approval").
                      --------------------

                                                                              14
<PAGE>

     7.   Miscellaneous.
          -------------

          7.1   Survival of Warranties.  The warranties and representations of
                ----------------------
the Company and the Purchasers contained herein shall terminate on the second
anniversary of the Closing.

          7.2   Transfer; No Third Party Beneficiaries.  This Agreement and each
                --------------------------------------
party's rights and obligations hereunder shall not be assigned without the prior
written consent of the other party; provided, that a Purchaser may transfer its
                                    --------
rights hereunder to an affiliate, so long as such affiliate agrees in writing to
be bound by all obligations under this Agreement.  Nothing in this Agreement,
express or implied, is intended to confer upon any party other than the parties
hereto or their respective successors and assigns any rights, remedies,
obligations, or liabilities under or by reason of this Agreement.

          7.3   Governing Law.  This Agreement and all acts and transactions
                -------------
pursuant hereto and the rights and obligations of the parties hereto shall be
governed by and construed in accordance with the laws of the State of Delaware,
without giving effect to principles of conflicts of laws.

          7.4   Counterparts.  This Agreement may be executed in two or more
                ------------
counterparts, each of which shall be deemed an original and all of which
together shall constitute one instrument.

          7.5   Titles and Subtitles.  The titles and subtitles used in this
                --------------------
Agreement are used for convenience only and are not to be considered in
construing or interpreting this Agreement.

          7.6   Notices.  Any notice required or permitted by this Agreement
                -------
shall be in writing and shall be deemed sufficient upon delivery, when delivered
personally or by overnight courier or sent by telegram or fax, or forty-eight
(48) hours after being deposited in the U.S. mail, as certified or registered
mail, with postage prepaid, addressed to the party to be notified at such
party's address as set forth on the signature page hereto, or as subsequently
modified by written notice, and if to the Company, with copies to the General
Counsel of the Company at the address of the Company set forth below and Simpson
Thacher & Bartlett, 3373 Hillview Avenue, Suite 250, Palo Alto, CA 94304,
Attention: William H. Hinman, telecopy no: (650)-251-5002).

          7.7   Finder's Fee.  Each party represents that it neither is nor will
                ------------
be obligated for any finder's fee or commission in connection with this
transaction.  Each Purchaser agrees to indemnify and to hold harmless the
Company from any liability for any commission or compensation in the nature of a
finder's fee (and the costs and expenses of defending against such liability or
asserted liability) for which such Purchaser or any of its officers, employees,
or representatives is responsible.  The Company agrees to indemnify and hold
harmless each Purchaser from any liability for any commission or compensation in
the nature of a finder's fee (and the costs and expenses of defending against
such liability or asserted liability) for which the Company or any of its
officers, employees or representatives is responsible.

                                                                              15
<PAGE>

         7.8   Fees and Expenses.  Except as otherwise specifically provided
               -----------------
herein, the Company and the Purchasers shall pay their respective fees and other
expenses in connection with the negotiation, execution, delivery and performance
of the Agreements.

         7.9   Attorney's Fees.  If any action at law or in equity (including
               ---------------
arbitration) is necessary to enforce or interpret the terms of any of the
Agreements, the prevailing party shall be entitled to reasonable attorney's
fees, costs and necessary disbursements in addition to any other relief to which
such party may be entitled.

         7.10  Amendments and Waivers.  Any term of this Agreement may be
               ----------------------
amended or waived only with the written consent of the Company and each of the
Purchasers.  Any amendment or waiver effected in accordance with this Section
7.10 shall be binding upon each Purchaser and each transferee of the Preferred
Stock, each future holder of all such Preferred Stock, each transferee and
future holder of Common Stock issued upon conversion of Preferred Stock and the
Company.

         7.11  Severability.  If one or more provisions of this Agreement are
               ------------
held to be unenforceable under applicable law, the parties agree to renegotiate
such provision in good faith.  In the event that the parties cannot reach a
mutually agreeable and enforceable replacement for such provision, then (a) such
provision shall be excluded from this Agreement, (b) the balance of the
Agreement shall be interpreted as if such provision were so excluded and (c) the
balance of the Agreement shall be enforceable in accordance with its terms.

         7.12  Delays or Omissions.  No delay or omission to exercise any right,
               -------------------
power or remedy accruing to any party under this Agreement, upon any breach or
default of any other party under this Agreement, shall impair any such right,
power or remedy of such non-breaching or non-defaulting party nor shall it be
construed to be a waiver of any such breach or default, or an acquiescence
therein, or of or in any similar breach or default thereafter occurring; nor
shall any waiver of any single breach or default be deemed a waiver of any other
breach or default theretofore or thereafter occurring.  Any waiver, permit,
consent or approval of any kind or character on the part of any party of any
breach or default under this Agreement, or any waiver on the part of any party
of any provisions or conditions of this Agreement, must be in writing and shall
be effective only to the extent specifically set forth in such writing.  All
remedies, either under this Agreement or by law or otherwise afforded to any
party, shall be cumulative and not alternative.

         7.13  Entire Agreement.  This Agreement, and the documents referred to
               ----------------
herein, constitute the entire agreement between the parties hereto pertaining to
the subject matter hereof, and any and all other written or oral agreements
relating to the subject matter hereof existing between the parties hereto are
expressly canceled.

         7.14  Confidentiality.  Except as provided below, each party hereto
               ---------------
agrees that, except with the prior written permission of the other party, it
shall at all times keep confidential and not divulge, furnish or make accessible
to anyone any confidential information, knowledge or data concerning or relating
to the business or financial affairs of the other party to which such party has
been or shall become privy by reason of the Agreements, discussions or
negotiations relating to the Agreements, the performance of its obligations

                                                                              16
<PAGE>

thereunder or the ownership of Stock purchased hereunder. The provisions of this
Section 7.14 shall be in addition to, and not in substitution for, the
provisions of any separate nondisclosure agreement executed by the parties
hereto with respect to the transactions contemplated by the Agreements.
Notwithstanding the foregoing, nothing herein shall prevent any party from
disclosing (i) such information that has been publicly disclosed, (ii) such
information that becomes available to the party on a non-confidential basis from
a source other than the other party hereto, provided that such source is not
bound by a confidentiality agreement with such other party, (iii) information
required to be disclosed pursuant to subpoena or other court process or
otherwise required to be disclosed by law or the regulations of any securities
exchange (provided that, to the extent practicable, advance notice is given to
the party whose confidential information is to be disclosed so that such party
can attempt to obtain a protective order) and (iv) such information that was
known to the party prior to its first receipt from the other party.

         7.15  Publicity.  After the execution of this Agreement, any of the
               ---------
parties may issue a press release disclosing that the Purchasers have agreed to
invest in the Company and the terms of the future relationship between the
parties in a form approved by the other party, which approval will not be
unreasonably withheld, conditioned or delayed.  In addition, any party may
disclose such information regarding the Purchasers' investment and the
relationship between the parties as required by law or the regulations of any
securities exchange.

         7.16  Termination.  This Agreement may be terminated and the
               -----------
transactions contemplated hereby may be abandoned at any time prior to the
Closing:

         (i)   at any time by mutual written consent of the Company and each of
      the Purchasers; or

         (ii)  by any party hereto if the Closing does not occur on or prior to
      October 31, 2000; (provided, that if on October 31, 2000 any
      authorization, approval or permit of any governmental authority or
      regulatory body of the United States or of any state that is required in
      connection with the lawful issuance and sale of the Stock pursuant to this
      Agreement has not been obtained, then no party shall be entitled to
      terminate this Agreement pursuant to this clause (ii) until December 15,
      2000 and then only if the Closing has not occurred on or prior to such
      date).

     Upon any such termination, this Agreement shall become void and of no
further effect, except for Sections 7.3, 7.7, 7.8, 7.9, 7.14 and this Section
7.16 which shall survive such termination.

                           [Signature Pages Follow]

                                                                              17
<PAGE>

     The parties have executed this Preferred Stock Purchase Agreement as of the
date first written above.

                                       COMPANY:

                                       DRUGSTORE.COM, INC.

                                       By:/s/ David Rostov
                                          --------------------------------------
                                       Name:  David Rostov
                                       Title: Chief Financial Officer

                                       Address: 13920 SE Eastgate Way, Suite 300
                                                Bellevue, WA 98005

           Signature Page to the Preferred Stock Purchase Agreement
<PAGE>

                                     PURCHASERS:

                                     KPCB VIII L.P.

                                     By:     /s/ Brook H. Byers
                                            ____________________________________
                                     Name:  Brook H. Byers
                                            ____________________________________
                                     Title: General Partner
                                            ____________________________________
                                     Address: 2750 Sand Hill Rd.
                                              __________________________________
                                              Menlo Park, CA 94025
                                              __________________________________

           Signature Page to the Preferred Stock Purchase Agreement
<PAGE>

                                     KPCB VIII FOUNDERS FUND, L.P.

                                     By:    /s/ Brook H. Byers
                                            ____________________________________
                                     Name:  Brook H. Byers
                                            ____________________________________
                                     Title: General Partner
                                            ____________________________________
                                     Address: 2750 Sand Hill Rd.
                                              __________________________________
                                              Menlo Park, CA 94025
                                              __________________________________

           Signature Page to the Preferred Stock Purchase Agreement
<PAGE>

                                     VULCAN VENTURES INCORPORATED

                                     By:     /s/ William D. Savoy
                                            ------------------------------------
                                     Name:       William D. Savoy
                                            ------------------------------------
                                     Title:      President
                                            ------------------------------------
                                     Address:  110-110th Ave. NE, Ste. 550
                                              ----------------------------------
                                               Bellevue, WA 98004
                                              ----------------------------------

           Signature Page to the Preferred Stock Purchase Agreement
<PAGE>

                                     [Other Purchasers].

                                     By:     L. John Doerr by
                                            ------------------------------------
                                     Name:   Barbara S. Hager
                                            ------------------------------------
                                     Title:  his attorney in fact
                                            ------------------------------------

                                     Address:  2995 Woodside Road
                                              ----------------------------------
                                               No. 400-402
                                              ----------------------------------
                                               Woodside, CA 94062

           Signature Page to the Preferred Stock Purchase Agreement

<PAGE>

                                  SCHEDULE I
                                  ----------

Purchaser                                     Purchase Commitment
---------                                     -------------------

KPCB VIII L.P.                                   $  14,178,000
KPCB Founders Fund, L.P.                         $     822,000
L. John Doerr                                    $   5,000,000
Vulcan Ventures Incorporated                     $2,682,825.00

Total
-----
<PAGE>

                                   EXHIBITS
                                   --------

Exhibit A- Certificate of Designation of Series 1 Preferred Stock
Exhibit B- Amended and Restated Certificate of Incorporation of the Company
Exhibit C- Matters to be covered in legal opinion of Simpson Thacher & Bartlett
Exhibit D- Persons to deliver Voting Agreements
Exhibit E- Form of Voting Agreement
Exhibit F- Matters to be covered in legal opinion of the General Counsel of the
           Company
<PAGE>

                                   EXHIBIT A
                                   ---------

            CERTIFICATE OF DESIGNATIONS OF SERIES 1 PREFERRED STOCK
<PAGE>

                                   EXHIBIT B
                                   ---------

                       AMENDED AND RESTATED CERTIFICATE
                        OF INCORPORATION OF THE COMPANY

<PAGE>

                                   EXHIBIT C
                                   ---------

                   MATTERS TO BE COVERED BY LEGAL OPINION OF
                          SIMPSON THACHER & BARTLETT
<PAGE>

                                   EXHIBIT D
                                   ---------

                     PERSONS TO DELIVER VOTING AGREEMENTS

Kleiner Perkins Caufield & Byers VIII, L.P.

KPCB Life Sciences Zaibatsu Fund II, L.P.

KPCB VIII Founders Fund, L.P.

Amazon.com, Inc.

Maveron Equity Partners, L.P.

Vulcan Ventures Incorporated

Rite Investments Corp.

General Nutrition Investment Company

Peter Neupert

Peter Neupert and Sheryl Neupert, Tenants in Common

Kal Raman

Mark L. Silverman

David Rostov

David Rostov, as custodian

Judith H. McGarry

Drugstore.com Foundation

Hearst Communications, Inc.

Integral Capital Partners IV, L.P.

Integral Capital Partners IV MS Side Fund, L.P.

Integral Capital Partners V, L.P.

Integral Capital Partners V Side Fund, L.P.

Baron Asset Fund

Baron Capital Funds Trust

L. John Doerr
<PAGE>

                                   EXHIBIT E
                                   ---------

                           FORM OF VOTING AGREEMENT
<PAGE>

                                   EXHIBIT F
                                   ---------

                   MATTERS TO BE COVERED BY LEGAL OPINION OF

                        GENERAL COUNSEL OF THE COMPANY<PAGE>

                            CONFIDENTIAL TREATMENT

                                                                    Exhibit 10.3

                         AMENDMENT NO. 1 TO AGREEMENT

     This Amendment No. 1 to Agreement (this "Amendment") dated as of July 29,
2000, is made and entered into by and between Amazon.com Commerce Services, Inc.
("ACI"), an indirect wholly owned subsidiary of Amazon.com, Inc. ("Amazon.com")
and drugstore.com, Inc. ("drugstore.com") with respect to that certain Agreement
between the Parties dated as of January 24, 2000 (the "Agreement").  All
capitalized terms used in this Amendment and not otherwise defined shall have
the meaning attributed to them in the Agreement.  References to section numbers
below are references to sections of the Agreement.

     ACI and drugstore.com agree as follows:

     1.    A new definition of "Qualifying New Customer" is hereby added Section
1, reading as follows:

     "Qualifying New Customer" means, with respect to any Year after Year 1, any
person or entity who becomes a New Customer after the [Confidential Treatment]
New Customer in such Year (i.e., New Customers [Confidential Treatment] in any
Year after Year 1).

     2.    A new definition of "New Customer" is hereby added to Section 1,
reading as follows:

     "New Customer" means a person or entity who at any time during the Term
purchases a product through the Amazon.com Health and Beauty Section; provided,
that such person or entity had not previously purchased a product from
drugstore.com.

     3.    A new definition of "Specified Amazon.com Site Functionalities" is
hereby added to Section 1, reading as follows:

     "Specified Amazon.com Site Functionalities" means the following specific
Amazon.com Site Functionalities: (a) payment and transaction functionality
available to users of the Amazon.com Site for purchasing products (including
without limitation, Shared Cart Functionality and Shared Checkout
Functionality); (b) Amazon.com Site-wide search functionality; and (c) only with
respect to the Home Page of the Amazon.com Health and Beauty Section (and no
other page of the Amazon.com Health and Beauty Section), the Amazon.com Site
Functionality associated with the "tab" structure (or any successor top-level
global site navigation tool) as it appears on the Amazon.com Site generally.

     4.    A new definition of "Shared Cart Functionality" is hereby added to
Section 1, reading as follows:

     "Shared Cart Functionality" means the Amazon.com Site Functionality
available to users of the Amazon.com Site and its Product Sections that
incorporates item or promotional displays (e.g., discounts, tax, shipping,
hazardous materials shipping restrictions and other order-related displays that
are used by drugstore.com and other third parties who sell products through
Amazon.com Site Product Sections) relating to products that a user has selected
for possible purchase.

<PAGE>

                            CONFIDENITAL TREATMENT

     5.    A new definition of "Shared Checkout Functionality" is hereby added
to Section 1, reading as follows:

     "Shared Checkout Functionality" means the Amazon.com Site Functionality
available to users of the Amazon.com Site and its Products Sections that allows
the user in a single transaction to purchase all items in the user's shopping
cart.

     6.    Section 2.2 is hereby amended in its entirety to read as follows:

     "2.2  Phase Two - Catalog Integration and Single Checkout.

           2.2.1  Following the implementation of Phase One, ACI in consultation
with drugstore.com will, as set forth below in this Section 2.2, determine the
design and development schedule for implementation of certain of the Amazon.com
Site Functionalities to enable Amazon.com customers to shop and pay for non-
prescription products available on the drugstore.com Site (along with shopping
and paying for all other products available on the Amazon.com Site) while
shopping on the Amazon.com Site and otherwise to further integrate aspects or
portions of the drugstore.com Site into the Amazon.com Site and Amazon.com Site
Functionality (such further integration, "Phase Two").

           2.2.2  The implementation of the Specified Amazon.com Site
Functionalities within the Amazon.com Health and Beauty Section in Phase Two
will be determined by Amazon.com in consultation with drugstore.com (including,
without limitation, as to the appearance and positioning of Amazon.com Site
features that implement the Specified Amazon.com Site Functionalities).  Subject
to the foregoing sentence, the general shopping experience within the Amazon.com
Health and Beauty Section will be generally the same as the shopping experience
on the drugstore.com Site and the coloring, graphics, logos, editorial,
merchandising, features and services and other "look and feel" aspects of the
Amazon.com Health and Beauty Section will remain generally the same as on the
drugstore.com Site (except with respect to the implementation of the Specified
Amazon.com Site Functionalities) or as otherwise agreed to by drugstore.com,
given the technical and production issues associated with the implementation of
Phase Two.  drugstore.com acknowledges that in Phase Two, it will be one
participant in an e-commerce "platform" being developed by Amazon.com, and that
therefore, the nature, timing and scope of integration efforts to be undertaken
as part of Phase Two will be determined by Amazon.com (in consultation with
drugstore.com), subject to the specific requirements as to appearance and
functionality set forth in this Section 2.2.2; provided, however, that: (a)
Amazon.com acknowledges that the primary intent of Phase Two is to maximize user
conversion rates and enhance the shopping experience on the Amazon.com Health
and Beauty Section and the rest of Amazon.com's e-commerce platform; (b) with
respect to any functionalities other than the Specified Amazon.com Site
Functionalities, if drugstore.com and Amazon.com cannot agree upon the
appropriate implementation of such functionalities, such functionalities shall
not be implemented for the Amazon.com Health and Beauty Section; provided
further that with respect to any Shared Checkout Functionality, drugstore.com
will use reasonable best efforts to implement the same.  To the extent that
Phase Two involves the integration of portions or aspects of the drugstore.com
Site into the Amazon.com Site, drugstore.com shall not be required to comply
with those requirements of Section 2.4 relating to the maintenance and
appearance of the drugstore.com Site that are obviated by reason of Amazon.com's
integration of such portions or aspects of the drugstore.com Site into the
Amazon.com Site (drugstore.com agreeing, however, it shall nonetheless continue
to comply, without limitation, with the provisions of Section 2.4 (b), (c) and
(d)).

           2.2.3  Amazon.com shall notify drugstore.com in advance of the date
of commencement of Phase Two. Amazon.com shall not unduly delay the commencement
of Phase Two

<PAGE>

                            CONFIDENTIAL TREATMENT

relative to similar integration efforts for other Amazon.com Product Sections
through which third parties offer products, it being understood, however, that
Amazon.com shall not be required to necessarily give the implementation of all
aspects of Phase Two first priority among all such integration efforts). In
furtherance of Phase Two, after Amazon.com gives drugstore.com notice of the
general nature, scope and scheduling of any content, functionality or other
items to be implemented as part of Phase Two: (a) drugstore.com will perform any
activities necessary to implement any Specified Amazon.com Site Functionalities
for the Amazon.com Health and Beauty Section within a commercially reasonable
time frame after Amazon.com makes the same available (provided, however, that
with respect to any Shared Checkout Functionality, drugstore.com shall only be
required to use its reasonable best efforts to implement the same); (b)
drugstore.com will use its commercially reasonable efforts to assist Amazon.com
in implementing any other content, functionality and other items required in
connection with the implementation of Phase Two within thirty (30) days after
Amazon.com makes the same available; and (c) Amazon.com will cooperate with
drugstore.com to implement any Specified Amazon.com Site Functionalities in such
manner and on such schedules as Amazon.com may specify, and to implement any
other content, functionality and other items that the Parties agree will be
implemented in Phase Two in such manner and on such schedules as the Parties may
agree upon. drugstore.com agrees, for the avoidance of doubt, that any Specified
Amazon.com Site Functionalities and related Technology are developed for use
across the Amazon.com Site and the e-commerce platform to be used generally with
respect to Amazon.com Product Sections through which third parties may offer
products, and not specifically for the purpose of linking to or communicating
between the Amazon.com Site and drugstore.com Site.

           2.2.4  Customers who purchase products through the Amazon.com Health
and Beauty Section are customers of ACI, Amazon.com and drugstore.com.
drugstore.com will be solely responsible for all order fulfillment and customer
service for orders of products purchased from drugstore.com through the
Amazon.com Health and Beauty Section.  The Parties will agree upon a means, that
complies with all applicable laws, regulations and orders of any governmental
authority of competent jurisdiction, whereby drugstore.com will be provided with
or otherwise enabled to receive all order-related and customer-related data
necessary for drugstore.com to fulfill its order fulfillment and customer
service responsibilities as well as to recognize and transact with an Amazon.com
Heath and Beauty Section customer as a repeat customer on the drugstore.com
Site.  Such information may include products ordered, name, address, email
address and credit card information of the purchaser and other necessary
information.  drugstore.com shall be free to use such data and communicate with
such customers as it uses such data for, and as it communicates with, its other
customers, subject to Section 2.7.  All revenues from sales of products or
services in the Amazon.com Health and Beauty Section, other than cross-promoted
products from other Amazon.com Product Sections, shall be drugstore.com revenues
and Amazon.com and ACI shall have no right to any revenue share or other fees,
except as set forth in Section 5.3.  The Parties shall implement Phase Two in a
manner that does not subject ACI, Amazon.com and their Affiliates to federal,
state or local regulations involving pharmacists, over the counter drugs or
homeopathic drugs and does not subject drugstore.com to any additional
regulation of such kind, and further does not create any jurisdiction or
authority for any governmental authority to impose material additional
obligations to collect sales tax, use tax or similar tax in connection with any
sales of products by ACI, Amazon.com, drugstore.com or their Affiliates.  The
Parties will agree to pursue in good faith ways to permit customers to order
prescription products through the Amazon.com Health and Beauty Section in Phase
Two, and cross-promote products from other Amazon.com Product Sections."

     7.    Section 2.7 is hereby amended in its entirety to read as follows:

<PAGE>

                            CONFIDENTIAL TREATMENT

     "2.7  Customer Contacts and Referral Information.  drugstore.com will not
disclose any personally identifying information regarding New Customers to any
third party, or use any such information for any purpose other than as provided
below in this Section 2.7.  Without limiting the generality of the foregoing,
drugstore.com shall not during the Term solicit, contact or communicate in any
manner with any New Customer except to the extent necessary in connection with
the fulfillment of sale transactions conducted on the Amazon.com Health and
Beauty Section or to the extent that a communication is requested or expected by
the New Customer.  "Requested or expected" includes ordinary course newsletters,
refill and replenishment reminders, EmedAlert and other similar communications
that drugstore.com provides to its customers as part of its services that the
New Customer has reason to expect will be delivered; provided, however, that
drugstore.com may deliver one (1) promotional communication per calendar quarter
during the Term to each New Customer, so long as no such promotional
communication contains any link or reference to, or otherwise seeks to direct
any person to, any page of any Web Site other than a page of the Amazon.com
Health and Beauty Section (including the drugstore.com Site).  No promotional
communication by drugstore.com with any New Customer shall contain any offer
from or reference to any competitor of ACI, Amazon.com or their Affiliates
(including, without limitation, in the packaging of any shipment or other
communication made in connection with the fulfillment of a sale transaction).
Subject to the foregoing, drugstore.com may use non-personal statistical
information regarding New Customers in the aggregate for any purpose, so long as
no New Customer can be specifically identified from such information.
drugstore.com acknowledges that Amazon.com may from time to time send
questionnaires or other inquiries ("Surveys") to persons who have purchased
products through the Amazon.com Health and Beauty Section asking for feedback
regarding their experience on the Amazon.com Health and Beauty Section.  To the
extent Amazon.com does not possess e-mail addresses or other contact information
necessary for the dissemination of such Surveys, drugstore.com shall assist in
disseminating the materials, which may include providing Amazon.com with the e-
mail addresses or other contact information, but is subject to compliance with
all parties' privacy polices.  To the extent that significant numbers of
customer responses are critical or negative in regard to their experience on the
Amazon.com Health and Beauty Section, drugstore.com will upon Amazon.com's
request use commercially reasonable efforts to address the issues raised in such
responses as promptly as possible."

     8.    A new Section 2.8 is hereby added to the Agreement, reading as
follows:

     "2.8  No Vendor Discrimination.  Neither Party will encourage, request or
require any third party not to, or enter into any agreement encouraging or
requiring any third party not to, provide or license any products (including
intangibles) or services to the other Party or its Affiliates; provided,
however, that the foregoing shall not prohibit either Party from entering into
exclusive licensing or distribution agreements with any third parties, so long
as such agreements do not specifically reference the other Party or its
Affiliates or subject the other Party or its Affiliates to prohibitions or
restrictions as to such products to which similarly-situated third parties are
not generally subjected."

     9.    Section 4.4 is hereby amended in its entirety to read as follows:

     "4.4  Traffic Data.  Throughout the Term as is reasonably available, on a
monthly basis, each Party will provide the other Party all relevant data
requested from time to time by the such Party concerning behavior on the
drugstore.com Site and the Amazon.com Health and Beauty Section, as the case may
be; provided, however, that notwithstanding any other provision of this
Agreement, neither Party shall be required to deliver to the other Party any
purchase-level data (i.e., data uniquely identified with a user that is provided
or generated in the course of a purchase transaction), except for delivery of e-
mail addresses as required to deliver Surveys pursuant to Section 4.4 (each
Party acknowledging, however, that the foregoing does not alter the Parties'
intent as set forth in Section 2.2

<PAGE>

                            CONFIDENTIAL TREATMENT

and 4.2 to cooperate in good faith and use commercially reasonable efforts to
maximize conversion rates and sales from or through the Amazon.com Health and
Beauty Section, and does not affect drugstore.com's right to retain New
Customers after the Term). The Parties will hold such data in confidence and
will not use it except in connection with their marketing efforts, or otherwise
in accordance with such reasonable guidelines as the Parties may agree upon.
Notwithstanding anything contained in this Section 4.4 or any other provision of
this Agreement: (a) neither Party will be required to deliver to the other Party
any user data in violation of its then-existing, generally applicable policies
regarding the protection of user information with respect to the drugstore.com
Site or the Amazon.com Site or in contravention of any applicable law,
regulation, judgment or order of any governmental authority of competent
jurisdiction; and (b) Amazon.com shall have the right from time to time to
review drugstore.com's policies and practices relating to the protection of user
data (and drugstore.com shall provide to Amazon.com reasonable cooperation as
requested by Amazon.com in connection therewith), and, if Amazon.com reasonably
determines that such policies and practices do not provide at least the same
level of protection for such data as Amazon.com itself provides with respect to
such data, Amazon.com shall notify drugstore.com of its concerns in reasonable
detail (and provide drugstore.com with such evidence as drugstore.com may
reasonably request to verify Amazon.com's provision of such level of protection
itself), and shall thereafter not be required to provide any such data to
drugstore.com unless and until drugstore.com addresses such concerns to
Amazon.com's reasonable satisfaction. Amazon.com will upon drugstore.com's
reasonable request provide drugstore.com with reasonable evidence regarding its
policies and practices relating to the protection of user data to permit
drugstore.com to substantiate that the same are commercially reasonable (and, if
the same are not commercially reasonable, Amazon.com will provide reasonable
cooperation to institute policies and practices that are commercially
reasonable)."

     10.  Section 5.3 is hereby amended in its entirety to read as follows:

     "5.3  Annual Fees and New Customer Bounties; Payments Processing Fees.

           5.3.1  During the Term, drugstore.com will pay ACI annual fees in the
amounts set forth below ("Annual Fees"):

           Year 1:  $27,000,000.00

           Year 2:  $15,000,000.00

           Year 3:  $15,000,000.00

           Subject to Section 10.5.2, drugstore.com will pay each of the Annual
Fees set forth above in four (4) equal installments due at the end of each
consecutive three month period of the Term following the Launch Date ("Quarterly
Payments")."

           5.3.2  In addition to the Annual Fees, drugstore.com will pay ACI a
bounty of [Confidential Treatment] for each Qualifying New Customer delivered in
each Year other than Year 1 (each, a "Qualifying New Customer Bounty").
Qualifying New Customer Bounties shall be paid in arrears on a quarterly basis
after drugstore.com begins receiving Qualifying New Customers, as follows:
within thirty (30) days after the end of any consecutive three month period of
the Term following the end of Year 1 (each a "Quarter"), drugstore.com shall
remit to Amazon.com the aggregate Qualifying New Customer Bounties payable for
Qualifying New Customers delivered in the preceding Quarter, together with a
report specifying in reasonable detail the number of Qualifying New Customers
delivered during the preceding Quarter and in the aggregate during the Year and
drugstore.com's calculation of the Qualifying New Customers delivered for the
preceding Quarter.
<PAGE>

                            CONFIDENTIAL TREATMENT

           5.3.3  In addition to the Annual Fees and Qualifying New Customer
Bounties called for by this Section 5.3, drugstore.com shall pay or reimburse
Amazon.com for any reasonable costs, fees and expenses incurred by Amazon.com or
its Affiliates in connection with processing payments for products purchased
through the Amazon.com Health and Beauty Section during Phase Two.  Unless the
Parties agree upon another means of payment, Amazon.com shall invoice
drugstore.com for such costs on a monthly basis, and drugstore.com shall pay
properly invoiced amounts within thirty (30) days after its receipt of any such
invoice.

     11.   Section 5.7 is hereby amended in its entirety to read as follows:

     "5.7  Allocation of Payments.  The Parties acknowledge and agree that the
Annual Fees and Qualifying New Customer Bounties shall be allocated as
consideration for advertising services and intangible rights granted by ACI to
drugstore.com hereunder, including the proprietary rights granted to
drugstore.com under Section 6, as set forth on Exhibit C."

     12.   Section 9.1.1 is hereby amended in its entirety to read as follows:

           "9.1.1  ACI and Amazon.com New Product Sections.  During the Term,
neither ACI nor Amazon.com will create or maintain a new Amazon.com Product
Section that offers, markets and sells Drugstore Products or Beauty Products,
provided, however that ACI or Amazon.com may offer and permit third parties to
offer other Beauty Products and Drugstore Products (excluding, with respect to
any third party, prescription products) in existing or new ACI Product Sections
as long as the annual gross revenue derived from such products does not exceed
15% of the combined annual gross revenue derived from sales of all products and
services offered by the ACI Product Sections offering such products (excluding
the Amazon.com Health and Beauty Section)."

     13.  Section 9.4 is hereby amended in its entirety to read as follows:

     "9.4  Records; Audit.   Each Party will, during the Term and for a period
of one (1) year thereafter, maintain complete and accurate books and records
sufficient to verify its compliance or non-compliance with the provisions of
this Section 9 (and, in the case of drugstore.com, Section 5.3.2).  Each Party
(the "Audited Party") will, upon at least thirty (30) days' prior written
request by the other Party (the "Auditing Party"), allow an independent
certified public accounting firm selected by the Auditing Party and reasonably
acceptable to the Audited Party to audit such books and records at the Audited
Party's premises to the extent necessary to verify the Audited Party's
compliance or non-compliance with the provisions of this Section 9 (or, in the
case of drugstore.com, Section 5.3.2); provided, that: (a) any such audit is
conducted during normal business hours and in a manner designed to not
unreasonably interfere with the Audited Party's ordinary business operations;
(b) audits may not occur more frequently than once every twelve (12) months; and
(c) each such audit may only cover the period commencing after the period
covered by the last audit conducted pursuant to this Section, if any.  The
Auditing Party agrees that any information learned or disclosed by its auditor
in connection with such audit is Confidential Information of the Audited Party.
If any such audit reveals any material non-compliance with the provisions of
this Section 9 by the Audited Party (or, in the case of drugstore.com, Section
5.3.2), the Audited Party shall, within ten (10) days of its receipt of an
invoice therefor, reimburse the Auditing Party for all reasonable out-of-pocket
fees and expenses incurred by the Auditing Party in connection with the
applicable audit."

     14.  Exhibit C is hereby amended in its entirety to read as Exhibit C
          ---------                                              ---------
attached hereto.
<PAGE>

                            CONFIDENTIAL TREATMENT

     15.  This Amendment supersedes any previous or contemporaneous oral or
written agreements regarding the subject matter set forth above.  For the
avoidance of doubt, the Parties acknowledge and agree that the provisions of
Section 3.1 and Section 11.2 of the Agreement shall apply to this Amendment and
the transactions contemplated hereby.  Except as expressly amended by this
Amendment, the Agreement remains in full force and effect in accordance with its
terms.

     IN WITNESS WHEREOF, the Parties have executed this Amendment as of the date
first written above.

ACI                                         drugstore.com:
---                                         -------------

Amazon.com Commerce Services, Inc.          drugstore.com, inc.

By: /s/ Mark Britto                         By:  /s/ Peter M. Neupert
   --------------------------------            --------------------------------

Title:  Sr. V.P.                            Title:  CEO
      -----------------------------               -----------------------------

Notice Address:                             Notice Address:

ACI                                         drugstore.com, inc.
1200 12th Avenue South, Suite 1200          13920 S.E. Eastgate Way, Suite 300
Seattle, WA 98144                           Bellevue, WA  98005
Facsimile:  206-266-7010                    Facsimile:  425.372.3808

<PAGE>

                            CONFIDENTIAL TREATMENT

                                   EXHIBIT C

                             ALLOCATION OF PAYMENTS
<TABLE>
<CAPTION>
-------------------------------------------------------------------------------
      Year           Advertising Services            Intangible Assets
-------------------------------------------------------------------------------
<S>                  <C>                             <C>
        1                      3%                            97%
-------------------------------------------------------------------------------
        2                      3%                            97%
-------------------------------------------------------------------------------
        3                      3%                            97%
-------------------------------------------------------------------------------
</TABLE>

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