QuickLinks -- Click here to rapidly navigate through this document

Exhibit 10.14.1

FIRST AMENDMENT
TO
PREFERRED STOCK AND WARRANT PURCHASE AGREEMENT

    This First Amendment to Preferred Stock and Warrant Purchase Agreement (the
"Amendment") is made as of December 22, 2000 between MedicaLogic/Medscape, Inc.,
an Oregon corporation (the "Company"), and the Investors listed on Schedule A
hereto (the "Investors").

    The Company and the Investors are parties to a Preferred Stock and Warrant
Purchase Agreement dated as of December 22, 2000 (the "Agreement"). The parties
wish to amend the Agreement to reflect the purchase of additional securities by
one of the Investors.

    NOW, THEREFORE, the parties agree as follows:

    1.  All capitalized terms used herein and are defined herein shall have the
meanings assigned to such terms in the Agreement.

    2.  Section 2.5(a) of the Agreement is amended and restated to read in its
entirety as follows:

    "(a) At the Closing the authorized capital stock of the Company shall
consist of 100,000,000 shares of Common Stock, 50,000,000 shares of preferred
stock, of which 5,933,332 shares shall have been designated Series 1 Preferred
Stock. At December 17, 2000, 55,719,682 shares of Common Stock (which includes
shares of restricted Common Stock described below) and no shares of preferred
stock were issued and outstanding. At December 17, 2000, 2,287,844 shares of
Common Stock remained available for issuance under the Company's 1999 Employee
Stock Purchase Plan. At December 17, 2000, the aggregate number of shares of
restricted stock and options to purchase shares of Common Stock available to be
issued or granted pursuant to any stock option plan or stock incentive plan of
the Company or any Subsidiary was 959,779. At December 17, 2000, options to
purchase 9,143,282 shares of Common Stock were outstanding and 2,210,750 shares
of restricted Common Stock had been issued under such plans. Except for the
Series 1 Preferred Stock and the Warrants, shares issuable under the Company's
1999 Employee Stock Purchase Plan and the stock options referred to in the
preceding sentence (as may be updated pursuant to Section 5.16), there are no
options, warrants, conversion privileges, subscription or purchase rights or
other rights presently outstanding to purchase or otherwise acquire (x) any
authorized but unissued, unauthorized or treasury shares of the Company's
capital stock or (y) any securities of the Company convertible into or
exercisable or exchangeable for shares of Common Stock, and there are no
commitments, contracts, agreements, arrangements or understanding by the Company
to issue any such securities."

    3.  Schedule A to the Agreement is amended and restated to read in its
entirety as attached as Schedule A hereto.

    4.  Exhibit A to the Agreement is amended as follows:

(a) the first paragraph of Section D is amended and restated to read in its
entirety as follows:

    "D.  Series 1 Preferred Stock.  This Article II.D sets forth the
designation, relative rights, preferences and limitations of a new series of
Preferred Stock of the Corporation as determined by the Board of Directors of
the Corporation pursuant to its authority under ORS 60.134 and Article II.C.
above. The shares of such series shall be designated Series 1 Convertible
Redeemable Preferred Stock ("Series 1 Preferred Stock") and the number of shares
constituting such series shall be 5,933,332."

(b) Section (D)(7) is amended and restated to read in its entirety as follows:

    "7.  Protective Provisions.  So long as 2,966,666 shares of Series 1
Preferred Stock are outstanding (subject to adjustment for stock dividends,
splits or combinations or other

--------------------------------------------------------------------------------

recapitalizations), the Corporation shall not without first obtaining the
approval, by vote or written consent (which consent need not be unanimous and
may be obtained without a shareholders' meeting), of the holders of at least a
majority of the then outstanding shares of Series 1 Preferred Stock:

    (a) authorize any voluntary liquidation under applicable bankruptcy
legislation, any dissolution, liquidation or winding up of the Corporation or
any deemed dissolution, liquidation or winding up within the meaning of
Section 3(b);

    (b) effect or taking any action to facilitate any transaction or series of
transactions resulting in the disposition of more than 50% of the voting power
of the Corporation;

    (c) authorize any merger, acquisition or consolidation with any other
corporation or joint venture involving consideration (determined in accordance
with Section 3(c)) in excess of $5,000,000;

    (d) declare or pay any dividends or other distributions on the Corporation's
capital stock (other than a dividend payable solely in shares in Common Stock or
a dividend accruing pursuant to Section 2(b) hereof) or redeem, purchase or
otherwise acquire any share or shares of Preferred Stock (except as provided in
Section 4) or Common Stock; provided, however, that this restriction shall apply
neither to the repurchase of shares of Common Stock from employees, officers,
directors, consultants or other persons performing services for the Corporation
or any subsidiary pursuant to agreements under which the Corporation has the
option to repurchase such shares at cost or at cost upon the occurrence of
certain events, such as the termination of employment;

    (e) permit any subsidiary to issue and sell securities having a fair market
value (as determined in accordance with Section 3(c)) in excess of $5,000,000;

    (f)  sell more than $5,000,000 in its assets in a single or series of
related transactions or create or suffer to be imposed any lien, mortgage,
security interest or other charge on or against more than $5,000,000 of assets;

    (g) incur any indebtedness for borrowed money in excess of $5,000,000 in
aggregate principal amount;

    (h) redeem, purchase or otherwise acquire any indebtedness of the
Corporation (unless such indebtedness is otherwise due in accordance with its
terms);

    (i)  authorize any transactions with any affiliates (other than wholly-owned
subsidiaries of the Corporation); or

    (j)  amend or repeal any provision of the Corporation's Articles of
Incorporation or Restated Bylaws if such action would adversely affect the
relative rights, preferences and privileges of the Series 1 Preferred Stock
(including, without limitation, (A) the authorization, creation or issuance of
any Senior Capital Stock or Parity Capital Stock or any obligation or security
convertible into or exchangeable into, or evidencing a right to purchase, shares
of any class or series of Senior Capital Stock or Parity Capital Stock, (B) the
increase of the directors on the Corporation's Board of Directors to a number
greater than 12, or (C) the designation and issuance after the Series 1 Purchase
Date of any additional shares of Series 1 Preferred Stock)."

    5.  The first paragraph of Exhibit C to the Agreement is amended and
restated to read in its entirety as follows:

    "We have acted as counsel to MedicaLogic/Medscape, Inc., an Oregon
corporation (the "Company"), in connection with the sale by the Company to you
of an aggregate of 5,933,332 shares of the Company's Series 1 Convertible
Redeemable Preferred Stock, without par value, and Common Stock Purchase
Warrants (the "Warrants") to purchase an aggregate of 4,537,254 shares

2

--------------------------------------------------------------------------------

of its Common Stock, without par value, pursuant to the Preferred Stock and
Warrant Purchase Agreement dated as of December 22, 2000, as amended (the
"Agreement"). This opinion is delivered to you pursuant to Section 4.8 of the
Agreement. Capitalized terms not otherwise defined in this opinion shall have
the meanings ascribed to them in the Agreement or in the Legal Opinion Accord of
the ABA Section of Business Law (1991) (the "Accord")."

    6.  Recital G of Exhibit D to the Agreement is amended and restated to read
in its entirety as follows:

    G. The Company proposes to sell and issue up to 5,933,332 shares of Series 1
Convertible Redeemable Preferred Stock, without par value (the "Series 1
Preferred Stock"), and warrants to purchase up to 4,537,254 shares of common
stock, without par value (the "Series 1 Warrant Shares") in a closing pursuant
to the Preferred Stock and Warrant Purchase Agreement (the "Series 1 Agreement")
among the Company and certain investors listed on Signature Page I dated as of
December 22, 2000, as amended (the "Series 1 Purchasers")."

    7.  Except as expressly modified by this Amendment, the Agreement remains in
full force and effect as written.

    8.  This Amendment shall be governed by and construed under the laws of the
state of Oregon.

    9.  This Amendment may be executed in two or more counterparts, each of
which shall be deemed an original, but all of which together shall constitute
one and the same instrument.

(Signature page follows.)

3

--------------------------------------------------------------------------------

    IN WITNESS WHEREOF, the parties hereto have executed this Amendment as of
the date and years first written above.

    MEDICALOGIC/MEDSCAPE, INC.
 
 
By:

--------------------------------------------------------------------------------

Name: David Moffenbeier
Title: Chief Executive Officer
 
 
QUANTUM INDUSTRIAL PARTNERS LDC
 
 
By:

--------------------------------------------------------------------------------

Name:
Title:
 
 
SFM DOMESTIC INVESTMENTS LLC
 
 
By:

--------------------------------------------------------------------------------

Name:
Title:
 
 
RAM TRADING, LTD.
 
 
By:

--------------------------------------------------------------------------------

Name:
Title:

4

--------------------------------------------------------------------------------

SCHEDULE A

SCHEDULE OF INVESTORS

Investor

--------------------------------------------------------------------------------

  Number of
Shares of
Series 1
Preferred Stock

--------------------------------------------------------------------------------

  Number of
Warrants
Shares

--------------------------------------------------------------------------------

  Total Purchase
Price

--------------------------------------------------------------------------------

Quantum Industrial Partners LDC   1,666,666   1,274,509   $ 4,999,998.00 SFM
Domestic Investments LLC   1,666,666   1,274,509     4,999,998.00 Halifax Fund
LP   333,333   254,902     999,999.00 Lagunitas Partners LP   500,000   382,353
    1,500,000.00 Gruber & McBaine International   166,667   127,451    
500,001.00 Montrose Investments Ltd.   666,667   509,804     2,000,001.00
Coleman Swenson Hoffman Booth IV, LP   333,333   254,902     999,999.00
Crosslink Crossover Fund III, LP   88,000   67,295     264,000.00 Offshore
Crosslink Crossover Fund III, LP   6,000   4,588     18,000.00 Delta Growth, LP
  6,000   4,588     18,000.00 RAM Trading, Ltd.   333,333   254,902    
999,999.00 Cranshire Capital   166,667   127,451     500,001.00 TOTAL  
5,933,332   4,537,254   $ 17,799,994.00

--------------------------------------------------------------------------------

QuickLinks

FIRST AMENDMENT TO PREFERRED STOCK AND WARRANT PURCHASE AGREEMENT
SCHEDULE A SCHEDULE OF INVESTORS