Exhibit 4.5 CERTIFICATE OF DESIGNATION OF CONVERTIBLE PREFERRED STOCK, SERIES E OF XOMA CORPORATION (Pursuant to Section 151 of the Delaware General Corporation Law) XOMA CORPORATION, a corporation organized and existing under the General Corporation Law of the State of Delaware (the "Corporation"), does hereby certify that, pursuant to authority conferred upon the Board of Directors of the Corporation by the Restated Certificate of Incorporation of the Corporation, as amended, and pursuant to the provisions of Section 151 of the General Corporation Law of the State of Delaware, said Board of Directors duly adopted the following resolution on April 18, 1996, which resolution remains in full force and effect as of the date hereof: RESOLVED, that pursuant to the authority granted to and vested in the Board of Directors of the Corporation in accordance with the provisions of its Amended and Restated Certificate of Incorporation, the Board of Directors hereby creates a series of Preferred Stock, par value $.05 per share, of the Corporation and hereby states the designation and number of shares, and fixes the relative powers, preferences, rights, qualifications, limitations and restrictions thereof (in addition to the provisions set forth in the Restated Certificate of Incorporation of the Corporation, as amended, which are applicable to the Preferred Stock of all classes and series), as follows: Convertible Preferred Stock, Series E: Section A. Designation and Amount. Seven Thousand Five Hundred (7,500) shares of Preferred Stock, $.05 par value, are designated "Convertible Preferred Stock, Series E" with the powers, preferences, rights, qualifications, limitations and restrictions specified herein (the "Series E Preferred Stock"). Such number of shares may be increased or decreased by resolution of the Board of Directors; provided, that no decrease shall reduce the number of shares of Series E Preferred Stock to a number less than the number of shares then outstanding plus the number of shares reserved for issuance upon the exercise of outstanding options, rights or warrants or upon the conversion of any outstanding securities (including indebtedness) issued by the Corporation convertible into Series E Preferred Stock. Section B. Dividends. The Corporation shall not be required to pay, and the holders of the Series E Preferred Stock shall not be entitled to receive, any dividends on shares of the Series E Preferred Stock. Section C. Liquidation, Dissolution or Winding Up. Upon any liquidation, dissolution or winding up of the Corporation, whether voluntary or involuntary, before any payment or distribution shall be made to the holders of shares of the common stock of the Corporation, the holders of shares of Series E Preferred Stock shall be entitled to receive $10,000.00 per share of Series E Preferred Stock then held by such holders, plus an amount equal to declared and unpaid dividends and distributions thereon. After payment of the full liquidation preference of the Series E Preferred Stock set forth in the preceding sentence, the holders of the Series E Preferred Stock shall not be entitled to any further payments or distribution from the assets of the Corporation. Section D. Voting Rights. The holders of shares of Series E Preferred Stock shall not have any voting rights, except as required under the General Corporation Law of the State of Delaware. Section E. Redemption. 1. General. The Corporation at its option, in accordance with the terms and provisions of this Section 5, may, at any time and from time to time, redeem any or all shares of Series E Preferred Stock at a redemption price per share equal to a cash amount determined by multiplying the Conversion Price (as defined below) by the number of shares of Common Stock into which each such share of Series E Preferred Stock would be convertible pursuant to the provisions of Section 6 hereof. If fewer than all the outstanding shares of Series E Preferred Stock are to be redeemed, the shares to be redeemed shall be selected pro rata as nearly as practicable or by lot, or by such other method as the Board of Directors of the Corporation may determine to be fair and appropriate. 2. Notice of Redemption. The Corporation will provide notice of any redemption of shares of Series E Preferred Stock to the holders of record of the Series E Preferred Stock to be redeemed not less than five (5) nor more than sixty (60) days prior to the date fixed for such redemption. Such notice shall be provided by first-class mail, postage prepaid, to each holder of record of the Series E Preferred Stock to be redeemed, at such holder's address as it appears on the stock transfer books of the Corporation. Each such notice shall state, as appropriate, the following: a. the redemption date; b. the number of shares of Series E Preferred Stock to be redeemed and, if fewer than all the shares held by any holder are to be redeemed, the number of such shares to be redeemed from such holder; -2- c. the redemption price; d. the place or places where certificates for such shares are to be surrendered for redemption; e. the then effective Conversion Price (as determined under Section 6); and f. that the right of holders to convert shares of Series E Preferred Stock to be redeemed will terminate at the close of business on the business day next preceding the date fixed for redemption (unless the Corporation shall default in the payment of the redemption price). Any notice that is mailed as set forth above shall be conclusively presumed to have been duly given, whether or not the holder of shares of Series E Preferred Stock receives such notice, and failure to give such notice by mail, or any defect in such notice, to the holders of any shares designated for redemption shall not affect the validity of the proceedings for the redemption of any other shares of Series E Preferred Stock. 3. Mechanics of Redemption. Upon surrender in accordance with the aforesaid notice of the certificate for any shares so redeemed (duly endorsed or accompanied by appropriate instruments of transfer), the holders of record of such shares shall be entitled to receive the redemption price, without interest. In case fewer than all the shares represented by such certificate are redeemed, a new certificate representing the unredeemed shares shall be issued without cost to the holder thereof. Upon surrender of any shares so redeemed in accordance with this Section 5(C), the Corporation shall pay the full redemption amounts with respect to shares as provided herein. 4. Rights After Redemption. Notwithstanding that any certificates for shares to be redeemed have not been surrendered in accordance with Section 5(C), from and after the date of redemption designated in the notice of redemption (i) the shares represented thereby shall be deemed to be no longer outstanding, and (ii) all rights of the holders of such shares of Series E Preferred Stock shall cease and terminate, except only the right to receive the full redemption amounts as provided herein without interest. Section F. Conversion. 1. Right to Convert. Each share of Series E Preferred Stock shall be convertible, at the option of the holder thereof, into that number of shares of the Common Stock, par value $.0005 per share, of the Corporation (herein, the "Common Stock") as determined by dividing $10,000.00 by the Conversion Price (determined as provided below). The "Conversion Price" for any shares of Series E Preferred Stock issued in connection with a conversion pursuant to Section 4(a) of the Convertible Subordinated Note Agreement, dated as of April 22, 1996, between the Corporation and Genentech, Inc. (the "Note Agreement") shall be an amount per share equal to the Current Market Price (as defined below) of the Common Stock determined as of the first occurring Conversion Date (as such term is defined in Section 4(a) of the Note Agreement) (herein, the "Initial Issue Date"). The "Conversion Price" for any shares of Series E Preferred Stock issued in connection with a prepayment pursuant to Section -3- 3(d) of the Note Agreement shall be an amount per share equal to the Current Market Price of the Common Stock determined as of the date of the issuance of such shares (herein, the "Prepayment Issue Date"). The number of shares of Common Stock into which a share of Series E Preferred Stock is convertible is hereinafter referred to as the "Conversion Rate" of such series. The Conversion Price shall be subject to adjustment from time to time after the Initial Issue Date or applicable Prepayment Issue Date, as the case may be, as set forth in this Section 6. For purposes of this Section 6(A), "Current Market Price" shall mean the average daily Closing Prices (as defined below) per share of Common Stock for the fifteen (15) consecutive trading days immediately prior to the Initial Issue Date or applicable Prepayment Issue Date, as the case may be. "Closing Price" with respect to any securities on any day shall mean the closing sale price regular way on such day or, in case no such sale takes place on such day, the average of the reported closing bid and asked prices, regular way, in each case on the New York Stock Exchange, or, if such security is not listed or admitted to trading on such Exchange, on the principal national security exchange or quotation system on which such security is quoted or listed or admitted to trading, or, if not quoted or listed or admitted to trading on any national securities exchange or quotation system, the average of the closing bid and asked prices of such security on the over-the-counter market on the day in question as reported by the National Quotation Bureau Incorporated, or a similar generally accepted reporting service, or, if not so available, in such manner as furnished by any New York Stock Exchange member firm selected from time to time by the Board of Directors of the Corporation for that purpose, or a price determined in good faith by the Board of Directors of the Corporation or, to the extent permitted by applicable law, a duly authorized committee thereof, whose determination shall be conclusive. If any shares of Series E Preferred Stock shall be called for redemption, the right to convert the shares designated for redemption shall terminate at the close of business on the business day next preceding the date fixed for redemption unless the Corporation defaults in the payment of the redemption price. In the event of a default in the payment of the redemption price, the right to convert the shares designated for redemption shall terminate at the close of business on the business day next preceding the date that such default is cured. The shares of Common Stock issuable upon conversion of the shares of Series E Preferred Stock, when the same shall be issued in accordance with the terms hereof, are hereby declared to be and shall be fully paid and non-assessable shares of Common Stock in the hands of the holders thereof. 2. Automatic Conversion. Each share of Series E Preferred Stock shall automatically be converted into shares of Common Stock at its then effective Conversion Rate immediately upon the transfer of ownership by the initial holder to any third party which is not an Affiliate (as such term is defined below) of such holder. For purposes of this Certificate, the term "Affiliate" means, when used with respect to any specified person, any other person directly or indirectly controlling or controlled by or under direct or indirect common control with such specified person. For the purposes of this definition, "control," when used with respect to any person, means the power to direct the management and policies of such person, directly or indirectly, whether through the -4- ownership of voting securities, by contract or otherwise, and the terms "affiliated," "controlling" and "controlled" have meanings correlative to the foregoing. 3. Mechanics of Conversion. Each holder of Series E Preferred Stock who desires to convert the same into shares of Common Stock pursuant to this Section 6 shall surrender the certificate or certificates therefor, duly endorsed, at the office of the Corporation or any transfer agent for the Series E Preferred Stock, and shall give written notice to the Corporation at such office that such holder elects to convert the same. Such notice shall state the number of shares of Series E Preferred Stock being converted. Thereupon, the Corporation shall promptly issue and deliver at such office to such holder a certificate or certificates for the number of shares of Common Stock to which such holder is entitled and shall promptly pay in cash or, to the extent sufficient funds are not then legally available therefor, in Common Stock (at the fair market value of the Common Stock as of the date of such conversion as determined by the Board of Directors of this Corporation), any declared and unpaid dividends on the shares of Series E Preferred Stock being converted. Such conversion shall be deemed to have been made at the close of business on the date of such surrender of the certificates representing the shares of Series E Preferred Stock to be converted, and the person entitled to receive the shares of Common Stock issuable upon such conversion shall be treated for all purposes as the record holder of such shares of Common Stock on such date. 4. Adjustment for Subdivisions and Combinations. If the Corporation shall at any time or from time to time after the Initial Issue Date or applicable Prepayment Issue Date, as the case may be, effect a subdivision of the outstanding Common Stock, the Conversion Price in effect immediately before that subdivision shall be proportionately decreased. Conversely, if the Corporation shall at any time or from time to time after the Initial Issue Date or applicable Prepayment Issue Date, as the case may be, combine the outstanding shares of Common Stock into a smaller number of shares, the Conversion Price in effect immediately before the combination shall be proportionately increased. Any adjustment under this Section 6(D) shall become effective at the close of business on the date the subdivision or combination becomes effective. 5. Adjustment for Certain Dividends and Distributions. If the Corporation at any time or from time to time after the Initial Issue Date or applicable Prepayment Issue Date, as the case may be, makes, or fixes a record date for the determination of holders of Common Stock entitled to receive, a dividend or other distribution payable in additional shares of Common Stock, in each such event (without duplication for related events) the Conversion Price that is then in effect shall be decreased as of the time of such issuance or, in the event such record date is fixed, as of the close of business on such record date, by multiplying the Conversion Price then in effect by a fraction (1) the numerator of which is the total number of shares of Common Stock issued and outstanding immediately prior to the time of such issuance or the close of business on such record date, and (2) the denominator of which is the total number of shares of Common Stock issued and outstanding immediately prior to the time of such issuance or the close of business on such record date plus the number of shares of Common Stock issuable in payment of such dividend or distribution; provided, however, that if such record date is fixed and such dividend is not fully paid or if such distribution is not fully made on the date fixed therefor, the Conversion Price shall be recomputed accordingly as of the close of business on such record date and thereafter the -5- Conversion Price shall be adjusted pursuant to this Section 6(E) to reflect the actual payment of such dividend or distribution. 6. Adjustment for Other Dividends and Distributions. If the Corporation at any time or from time to time after the Initial Issue Date or applicable Prepayment Issue Date, as the case may be, makes, or fixes a record date for the determination of holders of Common Stock entitled to receive, a dividend or other distribution payable in securities of the Corporation other than shares of Common Stock, in each such event provision shall be made so that the holders of the Series E Preferred Stock shall receive upon conversion thereof, in addition to the number of shares of Common Stock receivable thereupon, the amount of other securities of the Corporation which they would have received had their Series E Preferred Stock been converted into Common Stock on the date of such event and had they thereafter, during the period from the date of such event to and including the conversion date, retained such securities receivable by them as aforesaid during such period, subject to all other adjustments called for during such period under this Section 6 with respect to the rights of the holders of the Series E Preferred Stock or with respect to such other securities by their terms. 7. Adjustment for Recapitalizations, etc. If at any time or from time to time after the Initial Issue Date or applicable Prepayment Issue Date, as the case may be, the Common Stock issuable upon the conversion of the Series E Preferred Stock is changed into the same or a different number of shares of any class or classes of stock, whether by recapitalization, reclassification or otherwise (other than a subdivision or combination of shares or stock dividend or a reorganization, merger, consolidation or sale of assets provided for elsewhere in this Section 6 or in Section 3), in any such event each holder of Series E Preferred Stock shall have the right thereafter to convert such stock into the kind and amount of stock and other securities and property receivable upon such recapitalization, reclassification or other change by holders of the maximum number of shares of Common Stock into which such shares of Series E Preferred Stock could have been converted immediately prior to such recapitalization, reclassification or change, all subject to further adjustment as provided herein or with respect to such other securities or property by the terms thereof. 8. Compliance with Laws. Notwithstanding any provision of this Section 6 to the contrary, no conversion of any share of Series E Preferred Stock shall be effective unless such conversion is permitted under then applicable laws. Section G. Reacquired Shares. Any shares of Series E Preferred Stock purchased or otherwise acquired by the Corporation in any manner whatsoever shall be retired and canceled promptly after the acquisition thereof. All such shares shall upon their cancellation become authorized but unissued shares of Preferred Stock and may be reissued as part of a new series of Preferred Stock subject to the conditions and restrictions on issuance set forth herein, in the Amended and Restated Certificate of Incorporation, or in any other Certificate of Designation creating a series of Preferred Stock or any similar stock or as otherwise required by law. Section H. Exclusion of Other Rights. Except as may otherwise be required by the General Corporation Law of the State of Delaware, shares of the Series E Preferred Stock shall not have any preferences or relative, participating, optional or other -6- special rights, other than those specifically set forth in this Certificate of Designation (as such Certificate of Designation may be amended from time to time) and in the Corporation's Amended and Restated Certificate of Incorporation, as amended. No shares of Series E Preferred Stock shall have any preemptive or subscription rights whatsoever as to any securities of the Corporation. Section I. Notice. All notices and other communications provided for or permitted to be given to the Corporation hereunder shall be made by hand delivery, next day air courier or certified first-class mail to the Corporation at its principal executive office (currently located on the date of the adoption of these resolutions at 2910 Seventh Street, Berkeley, California 94710, Attention: General Counsel). Section J. Transferability; Registration; Rights of Transferees. 1. Transferability. The Series E Preferred Stock may not be sold, assigned, conveyed, transferred, pledged, hypothecated or otherwise disposed of other than as set forth in, and in accordance with, that certain Common Stock and Convertible Note Purchase Agreement, dated as of April 22, 1996, between the Corporation and Genentech, Inc. 2. Transfer Mechanics; Registration. The Series E Preferred Stock certificate representing shares of Series E Preferred Stock to be transferred shall be duly endorsed by the transferring holder or by his duly authorized attorney or representative, or accompanied by proper evidence of succession, assignment or authority to transfer. In all cases of a transfer by an attorney, the original power of attorney, duly approved, or a copy thereof, duly certified, shall be deposited and remain with the Corporation. In case of a transfer by executors, administrators, guardians or other legal representatives, duly authenticated evidence of their authority shall be produced, and may be required to be deposited and to remain with the Corporation in its discretion. Upon any registration of a transfer, the Corporation shall deliver new Series E Preferred Stock certificates to the persons entitled to the shares of Series E Preferred Stock represented thereby. The Series E Preferred Stock certificates may be exchanged at the option of the holder thereof, when surrendered at the offices of the Corporation, for other Series E Preferred Stock certificates of different denominations, of like tenor and representing in the aggregate a like number of shares of Series E Preferred Stock. Any Series E Preferred Stock certificate so surrendered shall be promptly canceled by the Corporation and retired. Each Series E Preferred Stock certificate issued in exchange as provided above shall be substantially in the form of the Series E Preferred Stock certificate being exchanged and shall be subject to all of the terms and provisions hereof. 3. Required Legend(s). Each of the Series E Preferred Stock certificates shall contain the legend(s) required by that certain Common Stock and Convertible Note Purchase Agreement, dated as of April 22, 1996, between the Corporation and Genentech, Inc. Section K. Amendments. The Certificate of Designation filed pursuant hereto may be amended without notice to or the consent of any holder of Series E Preferred Stock to cure any ambiguity, defect or inconsistency, provided that such amendment does not adversely affect the rights of any holder of Series E Preferred Stock. Any provisions -7- of the Certificate of Designation filed pursuant hereto may be amended by the Corporation with the written consent of holders of Series E Preferred Stock representing a majority of the outstanding shares of Series E Preferred Stock. -8- IN WITNESS WHEREOF, the undersigned have executed this certificate as of April 22, 1996. ---------------------------------- Clarence L. Dellio Senior Vice President, Operations ---------------------------------- Christopher J. Margolin Vice President, General Counsel and Secretary -9-