1018-00001 · Client 1018 · Underwriting Agreement & Ancillary

new-lock-up-agreement-secondary.docx DOCUMENT Capital Markets

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LOCK-UP AGREEMENT

October 12, 2023

This Lock-Up Agreement (this "Agreement") is made and entered into as of October 12, 2023, in connection with the registered selling-stockholder secondary offering of shares of common stock, par value $0.001 per share (the "Common Stock"), of Penterra Pharmaceuticals Corp., a Delaware corporation (the "Company" or "PPC"), as more fully described herein.

PREAMBLE

Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017

Broadmark Capital Inc. 200 Park Avenue New York, NY 10166

As Representatives of the Several Underwriters

Ladies and Gentlemen:

The undersigned understands that Ridgeline Securities LLC ("Ridgeline") and Broadmark Capital Inc. ("Broadmark" and, together with Ridgeline, the "Representatives") are acting as representatives of the several underwriters (the "Underwriters") named in the Underwriting Agreement (as defined below). The Underwriters consist of Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC.

The undersigned further understands that the Representatives and the other Underwriters propose to enter into an Underwriting Agreement dated as of October 12, 2023 (the "Underwriting Agreement") among the Company, the selling stockholders named therein, and the Underwriters, providing for the registered selling-stockholder secondary offering (the "Offering") of an aggregate of 6,250,000 shares of Common Stock at a public offering price of $41.60 per share. In addition, the selling stockholders have granted the Underwriters a 30-day option to purchase up to an additional 937,500 shares of Common Stock solely to cover over-allotments, if any (the "Over-Allotment Option").

The Common Stock of PPC is listed on The Nasdaq Global Select Market under the ticker symbol "PNTR."

The Offering is being made pursuant to a shelf registration statement on Form S-3 (File No. 333-274851) previously filed by the Company with the Securities and Exchange Commission (the "SEC") and declared effective on August 22, 2023, together with a prospectus supplement filed pursuant to Rule 424(b)(5) under the Securities Act of 1933, as amended (the "Securities Act"), relating to the Offering.

The undersigned acknowledges that, in connection with the Company's initial public offering of Common Stock, which closed on April 17, 2023 (the "IPO"), the undersigned entered into a lock-up agreement containing restrictions on the transfer of shares of Common Stock for a period of 180 days following the closing of the IPO (the "IPO Lock-Up Agreement"). The undersigned further acknowledges that Ridgeline Securities LLC, Broadmark Capital Inc., and Morningstar Zanthor & Co., as the joint book-running managers in the IPO, have granted an early release and waiver of the restrictions set forth in the IPO Lock-Up Agreement, effective as of October 12, 2023, solely to permit the undersigned to participate in the Offering and to execute this Agreement in connection therewith.

As a material inducement to the Underwriters to enter into the Underwriting Agreement and to proceed with the Offering, and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the undersigned hereby agrees as follows:

Section 1. Definitions

As used in this Agreement, the following terms shall have the meanings set forth below:

"Closing Date" means October 17, 2023, being the date on which the closing of the Offering is expected to occur (the third business day following the date of pricing of the Offering, in accordance with Rule 15c6-1 under the Securities Exchange Act of 1934, as amended (the "Exchange Act")).

"Company" means Penterra Pharmaceuticals Corp., a Delaware corporation, and its successors and assigns.

"Hedging Transaction" means any swap, hedge, collar, forward sale contract, option, put, call, short sale, or similar arrangement or transaction, whether effected through a securities lending or borrowing arrangement or otherwise, that transfers to another person or entity, in whole or in part, any of the economic consequences of ownership of shares of Common Stock or any securities convertible into, exercisable for, or exchangeable for Common Stock, regardless of whether any such transaction is to be settled by delivery of shares of Common Stock, in cash, or otherwise.

"Lock-Up Period" means the period commencing on the Closing Date (October 17, 2023) and ending at the close of trading on the Nasdaq Global Select Market on the 90th calendar day thereafter (January 15, 2024). For the avoidance of doubt, if the 90th calendar day falls on a day that is not a trading day, the Lock-Up Period shall end at the close of trading on the immediately preceding trading day.

"Lock-Up Securities" means all shares of Common Stock of the Company beneficially owned (as such term is defined in Rule 13d-3 under the Exchange Act) by the undersigned as of the Closing Date (after giving effect to the sale of shares by the undersigned in the Offering, including, if applicable, shares sold pursuant to the Over-Allotment Option), together with any shares of Common Stock or securities convertible into, exercisable for, or exchangeable for Common Stock acquired by the undersigned after the Closing Date and during the Lock-Up Period. Without limiting the generality of the foregoing, Lock-Up Securities shall include:

(a) shares of Common Stock held of record by the undersigned;

(b) shares of Common Stock held through or attributed to the undersigned by reason of beneficial ownership of membership interests in Castellano Family Holdings LLC, a Delaware limited liability company;

(c) shares of Common Stock issuable upon the exercise of stock options, warrants, or other rights to acquire Common Stock, or upon the conversion or exchange of any securities convertible into or exchangeable for Common Stock, in each case held by or issuable to the undersigned; and

(d) any shares of Common Stock or securities described in clauses (a) through (c) above acquired by the undersigned after the date hereof and during the Lock-Up Period, whether by purchase, gift, grant, dividend, distribution, or otherwise.

"Representatives" means Ridgeline Securities LLC and Broadmark Capital Inc., acting as representatives of the several Underwriters.

"Transfer" means any (i) offer, sale, contract or agreement to sell, pledge, hypothecation, grant of any option to purchase, grant of any security interest in, lending, short sale, establishment of an open "put equivalent position" (within the meaning of Rule 16a-1(h) under the Exchange Act), or other disposition, directly or indirectly, of any Lock-Up Securities or any securities convertible into, exercisable for, or exchangeable for Lock-Up Securities, (ii) entry into any Hedging Transaction with respect to Lock-Up Securities, or (iii) filing of, or participation in the filing of, a registration statement with the SEC with respect to any of the foregoing. The term "Transfer" shall also include any transaction, arrangement, or understanding that has the same economic effect as, or is designed to achieve or have substantially similar economic consequences to, any of the transactions described in clauses (i) through (iii) above.

"Underwriters" means, collectively, Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC, and "Underwriter" means any one of them individually.

Section 2. Lock-Up Restrictions

The undersigned hereby agrees that, during the Lock-Up Period, the undersigned will not, and will cause any entity or person controlled by the undersigned not to, without the prior written consent of the Representatives (which consent may be withheld in the Representatives' sole discretion), directly or indirectly, Transfer any Lock-Up Securities, and specifically will not engage in any of the following activities:

(a) offer, sell, contract to sell, or otherwise dispose of, directly or indirectly, any Lock-Up Securities;

(b) pledge, hypothecate, encumber, or grant any security interest in any Lock-Up Securities;

(c) enter into any Hedging Transaction with respect to any Lock-Up Securities, including, without limitation, any short sale (whether or not against the box), any put or call option, any swap, or any other agreement, arrangement, or transaction that transfers to another person or entity, in whole or in part, the economic consequences of ownership of any Lock-Up Securities;

(d) make any demand for, or exercise any right with respect to, the registration under the Securities Act of any Lock-Up Securities or any security convertible into, exercisable for, or exchangeable for Lock-Up Securities, or cause to be filed, or cooperate with or assist in, any registration statement under the Securities Act with respect to any of the foregoing;

(e) engage in any transaction, whether by means of any agreement, arrangement, contract, instruction, or understanding (whether written or oral, formal or informal), that would result in a disposition of Lock-Up Securities; or

(f) publicly announce an intention to do, or publicly disclose the existence of any arrangement or agreement to do, any of the foregoing.

The restrictions set forth in this Section 2 shall apply regardless of whether any Transfer or other transaction described above would be effected or settled by the delivery of shares of Common Stock, in cash, or otherwise. The foregoing restrictions are expressly agreed to preclude the undersigned from engaging in any transaction that might be settled by means other than the delivery of physical shares of Common Stock, including, without limitation, through the use of derivative securities, cash-settled instruments, or other similar instruments.

Section 3. Shares Subject to Lock-Up — Selling Stockholder Detail

The following table sets forth, for each undersigned selling stockholder, the number of shares of Common Stock owned prior to the Offering, the number of base shares sold in the Offering, the number of shares subject to the Over-Allotment Option, and the number of shares retained (and therefore constituting Lock-Up Securities) after giving effect to the base Offering and, separately, after giving effect to the full exercise of the Over-Allotment Option:

For the avoidance of doubt, the Lock-Up Securities include all shares of Common Stock retained by each undersigned selling stockholder following the consummation of the Offering (whether or not the Over-Allotment Option is exercised), as well as any additional shares of Common Stock or securities convertible into, exercisable for, or exchangeable for Common Stock that are acquired by the undersigned during the Lock-Up Period, by any means whatsoever.

Section 4. Permitted Exceptions

Notwithstanding the restrictions set forth in Section 2 above, the undersigned may, without the prior written consent of the Representatives, effect the following transactions, subject in each case to the conditions specified below:

(a) Bona Fide Gifts. The undersigned may Transfer Lock-Up Securities as bona fide gifts to any person or entity; provided that (i) the donee executes and delivers to the Representatives a lock-up agreement in substantially the form hereof, containing restrictions that are no less restrictive than those set forth herein and that remain in effect for the remainder of the Lock-Up Period, and (ii) no public filing or announcement is required by or made voluntarily by the undersigned during the Lock-Up Period in connection with such Transfer, other than a filing on Form 5 made after the expiration of the Lock-Up Period, or if a filing under Section 16(a) of the Exchange Act is required during the Lock-Up Period, such filing shall include a statement that the Transfer was made as a bona fide gift and that the donee's shares remain subject to lock-up restrictions.

(b) Transfers to Immediate Family Members or Trusts. The undersigned may Transfer Lock-Up Securities to any member of the undersigned's immediate family (which, for purposes of this Agreement, shall include any relationship by blood, marriage, domestic partnership, or adoption, not more remote than first cousin) or to a trust, family limited partnership, limited liability company, or other estate planning vehicle for the direct or indirect benefit of the undersigned or the undersigned's immediate family members; provided that (i) the transferee executes and delivers to the Representatives a lock-up agreement in substantially the form hereof for the remainder of the Lock-Up Period, and (ii) no public filing or announcement is required by or made voluntarily by the undersigned during the Lock-Up Period in connection with such Transfer, other than a filing on Form 5 made after the expiration of the Lock-Up Period, or if a filing under Section 16(a) of the Exchange Act is required during the Lock-Up Period, such filing shall include a statement that the Transfer was made for estate planning purposes and that the transferee's shares remain subject to lock-up restrictions.

(c) Transfers to Affiliates or Wholly-Owned Entities. The undersigned may Transfer Lock-Up Securities to any affiliate (as defined in Rule 405 under the Securities Act) of the undersigned or to any entity wholly owned by the undersigned, including, in the case of any individual Castellano family member, transfers to or from Castellano Family Holdings LLC, and in the case of Castellano Family Holdings LLC, transfers to or from any of its members; provided that (i) the transferee executes and delivers to the Representatives a lock-up agreement in substantially the form hereof for the remainder of the Lock-Up Period, and (ii) no public filing or announcement is required by or made voluntarily by the undersigned during the Lock-Up Period in connection with such Transfer, other than a filing on Form 5 made after the expiration of the Lock-Up Period, or if a filing under Section 16(a) of the Exchange Act is required during the Lock-Up Period, such filing shall include a statement that the Transfer was made to an affiliate or wholly-owned entity and that the transferee's shares remain subject to lock-up restrictions.

(d) Transfers by Operation of Law. The undersigned may Transfer Lock-Up Securities by operation of law, including, without limitation, pursuant to an order of a court of competent jurisdiction, a qualified domestic relations order, a divorce settlement, or the laws of descent and distribution upon the death of the undersigned; provided that (i) the transferee agrees in writing to be bound by restrictions no less restrictive than those set forth herein for the remainder of the Lock-Up Period, and (ii) to the extent a filing under Section 16(a) of the Exchange Act is required, such filing shall include a footnote or statement noting that the Transfer was made by operation of law and that the transferee's shares remain subject to lock-up restrictions.

(e) Change of Control Transactions. The undersigned may Transfer Lock-Up Securities in connection with a bona fide third-party tender offer, merger, consolidation, or other similar transaction made to all holders of Common Stock involving a change of control of the Company, provided that such transaction has been approved by the Board of Directors of the Company; provided, however, that in the event that such tender offer, merger, consolidation, or other similar transaction is not consummated, the Lock-Up Securities held by the undersigned shall remain subject to the restrictions set forth in this Agreement for the remainder of the Lock-Up Period.

(f) Establishment of a 10b5-1 Trading Plan. The undersigned may establish a trading plan that is designed to comply in all respects with Rule 10b5-1 under the Exchange Act (a "10b5-1 Plan"); provided that (i) no sales or other dispositions of Lock-Up Securities occur under such 10b5-1 Plan during the Lock-Up Period, (ii) no public announcement or filing under the Exchange Act or otherwise is required to be made, or is voluntarily made, by or on behalf of the undersigned regarding the establishment of such 10b5-1 Plan during the Lock-Up Period, and (iii) the undersigned provides the Representatives with written notice of the establishment of any such 10b5-1 Plan promptly following its adoption.

(g) Exercise of Stock Options — Net/Cashless Basis and Tax Withholding. The undersigned may Transfer Lock-Up Securities to the Company in connection with the exercise of stock options on a net exercise or cashless exercise basis, or for the purpose of satisfying tax withholding obligations of the undersigned arising in connection with such exercise; provided that any shares of Common Stock received by the undersigned upon such exercise shall continue to be Lock-Up Securities and shall remain subject to the restrictions set forth in this Agreement for the remainder of the Lock-Up Period.

(h) Dispositions to Satisfy Tax Obligations. The undersigned may dispose of shares of Common Stock to satisfy tax obligations (including estimated tax obligations) arising in connection with the vesting of restricted stock units, restricted stock, or similar equity awards granted by the Company, including by means of a "sell-to-cover" transaction or by the Company's withholding of shares upon vesting; provided that (i) such disposition is limited to the minimum number of shares reasonably necessary to satisfy such tax obligations, and (ii) any shares of Common Stock remaining after such disposition shall continue to be Lock-Up Securities and shall remain subject to the restrictions set forth in this Agreement for the remainder of the Lock-Up Period.

In each case of clauses (a) through (d) above, no filing under Section 16(a) of the Exchange Act shall be required or shall be voluntarily made during the Lock-Up Period (other than a filing on Form 5 that is made after the expiration of the Lock-Up Period), and in the event any such filing is required to be made during the Lock-Up Period, such filing shall include a statement or footnote indicating that the Transfer was effected pursuant to the applicable exception under this Agreement and that the transferee's shares of Common Stock remain subject to the lock-up restrictions set forth herein.

Section 5. Consent of Representatives to Release

The Representatives may, in their sole and absolute discretion, at any time and from time to time, with or without cause, release all or any portion of the Lock-Up Securities of the undersigned, or any other selling stockholder subject to a lock-up agreement in substantially the form hereof, from all or any of the restrictions set forth in this Agreement, upon such terms and conditions as the Representatives may determine.

In the event the Representatives agree to release any Lock-Up Securities held by any selling stockholder from the restrictions set forth herein, the Representatives shall, to the extent required by the applicable rules, regulations, and interpretive guidance of the Financial Industry Regulatory Authority, Inc. ("FINRA"), including FINRA Rule 5131(d)(2) or any successor rule or regulation, provide the Company and each other selling stockholder subject to a lock-up agreement in substantially the form hereof with at least three (3) business days' advance written notice prior to the effective date of any such release, specifying (i) the identity of the selling stockholder whose Lock-Up Securities are being released, (ii) the number of shares being released, and (iii) the effective date of such release.

Unless otherwise agreed in writing by the Representatives and each affected selling stockholder, any release of Lock-Up Securities pursuant to this Section 5 shall be made on a pro rata basis among all selling stockholders who are subject to lock-up agreements in substantially the form hereof, based on the number of Lock-Up Securities held by each such selling stockholder relative to the total number of Lock-Up Securities held by all such selling stockholders in the aggregate.

Section 6. Representations and Warranties of the Undersigned

The undersigned hereby represents and warrants to the Representatives and to each of the Underwriters as follows:

(a) Power and Authority. The undersigned has full right, power, and authority to enter into this Agreement and to perform the undersigned's obligations hereunder. The execution and delivery of this Agreement by the undersigned and the performance by the undersigned of the obligations contemplated hereby do not require the consent, approval, or authorization of any person or entity, except as has already been obtained.

(b) Due Authorization (Entity Signatories). In the case of Castellano Family Holdings LLC, a Delaware limited liability company (EIN 87-2165438), the execution and delivery of this Agreement and the performance of the obligations hereunder have been duly authorized by all necessary limited liability company action, including, without limitation, the requisite approval of the managing member and, to the extent required, the other members of Castellano Family Holdings LLC, and no further action on the part of Castellano Family Holdings LLC or any of its members is necessary to authorize the execution, delivery, or performance of this Agreement.

(c) Binding Obligation. This Agreement constitutes a legal, valid, and binding obligation of the undersigned, enforceable against the undersigned in accordance with its terms, except as enforceability may be limited by (i) applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent conveyance, or similar laws relating to or affecting the enforcement of creditors' rights generally and (ii) general principles of equity, whether considered in a proceeding at law or in equity.

(d) No Conflicts. The execution, delivery, and performance by the undersigned of this Agreement, and the consummation of the transactions contemplated hereby, do not and will not (i) violate, conflict with, or result in a breach of, or constitute a default under, any agreement, contract, indenture, mortgage, deed of trust, lease, instrument, certificate, order, judgment, decree, law, rule, or regulation to which the undersigned is a party or by which the undersigned or any of the undersigned's Lock-Up Securities are bound, (ii) result in the creation or imposition of any lien, charge, or encumbrance upon any Lock-Up Securities (other than as contemplated by this Agreement), or (iii) require any filing with, or approval, authorization, or consent of, any governmental authority or regulatory body, other than filings, if any, under Section 16(a) of the Exchange Act.

(e) No Inconsistent Agreements. The undersigned has not entered into, and agrees that during the Lock-Up Period the undersigned will not enter into, any agreement, arrangement, or understanding (whether written or oral, formal or informal) with any person or entity that is inconsistent with the restrictions and obligations set forth in this Agreement, or that would in any way limit, restrict, or impair the ability of the undersigned to comply in all respects with the terms and conditions of this Agreement.

Section 7. Stop Transfer Instructions

The undersigned hereby agrees and consents that the Company and its transfer agent, Pinnacle Trust & Transfer Co., located at 1 Ashbury Asset Advisors Plaza, 30th Floor, New York, NY 10004 (the "Transfer Agent"), are hereby authorized and directed to take the following actions:

(a) Decline to make any transfer of Lock-Up Securities on the books and records of the Company or the Transfer Agent if such transfer would constitute a violation or breach of this Agreement, and to refuse to register any such transfer until such time as the Representatives have confirmed in writing that such transfer is permitted under the terms of this Agreement or that the Lock-Up Period has expired.

(b) Place a notation, legend, or restrictive notation on the book-entry account maintained by the Transfer Agent for the undersigned's shares of Common Stock referencing the existence and terms of this Agreement, including a statement substantially to the effect that the shares are subject to the terms and conditions of a Lock-Up Agreement dated October 12, 2023, and may not be transferred except in compliance therewith.

The Company hereby agrees to cause the Transfer Agent to implement stop transfer instructions consistent with this Agreement promptly upon or prior to the Closing Date and to maintain such instructions in effect throughout the Lock-Up Period. The Company further agrees to cause the Transfer Agent to remove such stop transfer instructions and any related legends or notations promptly, and in any event within two (2) business days, following the expiration of the Lock-Up Period or upon the earlier termination of this Agreement in accordance with Section 10 hereof. The undersigned acknowledges that any attempt to Transfer Lock-Up Securities in violation of the stop transfer instructions or this Agreement shall be null and void and the Company and the Transfer Agent shall not be required to give any effect to such attempted Transfer on the books and records of the Company.

Section 8. No Effect on Existing Registration Rights

Nothing in this Agreement shall be construed to limit, modify, or otherwise affect any registration rights held by the undersigned pursuant to any registration rights agreement, investor rights agreement, or similar agreement entered into by and between the undersigned (or any of the undersigned's affiliates) and the Company (collectively, the "Registration Rights Agreements"), except that the undersigned shall not exercise, and hereby waives the right to exercise, any demand registration rights, piggyback registration rights, Form S-3 registration rights, or any other similar rights under the Registration Rights Agreements during the Lock-Up Period with respect to the Lock-Up Securities. For the avoidance of doubt, nothing in this Agreement shall prevent the undersigned from exercising registration rights with respect to the Lock-Up Securities following the expiration of the Lock-Up Period, subject to the terms and conditions of the applicable Registration Rights Agreements.

Section 9. Relationship to Underwriting Agreement

This Agreement is entered into as a condition to, and is supplemental to, the Underwriting Agreement dated October 12, 2023, among the Company, the selling stockholders named therein, and the Underwriters. The undersigned acknowledges that the execution and delivery of this Agreement by the undersigned is a material condition to the willingness of the Underwriters to enter into the Underwriting Agreement and to proceed with the Offering.

The representations, warranties, covenants, and agreements of the undersigned contained in this Agreement are in addition to, and not in substitution for, any representations, warranties, covenants, or agreements made by or on behalf of the undersigned (whether in the undersigned's capacity as a selling stockholder or otherwise) in or pursuant to the Underwriting Agreement. Nothing in this Agreement shall be deemed to modify, amend, or waive any provision of the Underwriting Agreement, except to the extent expressly set forth herein.

In the event of any conflict or inconsistency between the terms and provisions of this Agreement and the terms and provisions of the Underwriting Agreement with respect to the lock-up restrictions applicable to the undersigned's Lock-Up Securities, the more restrictive provision shall control and govern.

The undersigned further acknowledges that the selling stockholders have also executed a Selling Stockholder Power of Attorney and Custody Agreement dated October 12, 2023, appointing David Orenstein as attorney-in-fact and Pinnacle Trust & Transfer Co. as custodian, in connection with the Offering. Nothing in this Agreement shall be construed to limit, modify, or otherwise affect such appointment, and the undersigned's obligations hereunder shall be in addition to, and not in limitation of, any obligations of the undersigned under such Selling Stockholder Power of Attorney and Custody Agreement.

Section 10. Term

This Agreement shall become effective upon the Closing Date (October 17, 2023). Prior to the Closing Date, this Agreement shall not be effective and the undersigned shall have no obligations hereunder.

This Agreement shall automatically terminate and be of no further force or effect upon the earliest to occur of the following:

(a) the expiration of the Lock-Up Period, which shall occur at the close of trading on the Nasdaq Global Select Market on January 15, 2024 (the 90th calendar day following the Closing Date);

(b) the termination of the Underwriting Agreement, for any reason, prior to the closing of the Offering on the Closing Date; or

(c) the delivery by the Representatives of written notice to the undersigned releasing all of the Lock-Up Securities from the restrictions set forth in this Agreement.

If the Underwriting Agreement is terminated for any reason before the Closing Date, this Agreement shall be null and void ab initio, and neither the undersigned nor the Representatives shall have any rights, obligations, or liabilities hereunder.

Upon the termination of this Agreement, the undersigned shall have no further obligations hereunder, and the Company and the Transfer Agent shall promptly remove any stop transfer instructions, legends, or notations placed on the book-entry accounts of the undersigned pursuant to Section 7 hereof.

Section 11. Amendments and Waivers

This Agreement may not be amended, modified, or supplemented, nor may any provision hereof be waived, except by a written instrument duly executed by the undersigned and each of the Representatives. Any amendment, modification, supplement, or waiver effected in accordance with the foregoing sentence shall be binding upon the undersigned and the Representatives and their respective successors, heirs, personal representatives, and permitted assigns.

No waiver of any provision of this Agreement, or consent to any departure by the undersigned from the terms hereof, shall be effective unless set forth in a written instrument signed by the party against whom enforcement of such waiver is sought. Any waiver granted pursuant to this Section 11 shall be limited solely to the specific instance and for the specific purpose for which it is given and shall not constitute a waiver of, or estoppel with respect to, any subsequent breach of or failure to comply with any other provision of this Agreement.

No failure or delay by the Representatives in exercising any right, power, or remedy under this Agreement shall operate as a waiver thereof, nor shall any single or partial exercise of any right, power, or remedy preclude any other or further exercise thereof or the exercise of any other right, power, or remedy.

Section 12. Successors and Assigns

This Agreement and the rights, obligations, and restrictions contained herein shall be binding upon and shall inure to the benefit of the undersigned and the Representatives and their respective successors, heirs, executors, administrators, personal representatives, and permitted assigns, whether by merger, consolidation, operation of law, or otherwise.

The undersigned may not assign, delegate, or otherwise transfer this Agreement or any of the undersigned's rights or obligations hereunder to any person or entity without the prior written consent of the Representatives, and any attempted assignment, delegation, or transfer without such consent shall be null and void and of no force or effect.

The Representatives may assign their rights under this Agreement to any successor representatives or underwriters acting in connection with the Offering or any related offering, without the prior written consent of the undersigned, and any such assignee shall be entitled to enforce the provisions of this Agreement as if it were an original party hereto.

Section 13. Governing Law and Jurisdiction

This Agreement shall be governed by, and construed and enforced in accordance with, the laws of the State of Delaware, without giving effect to any choice-of-law or conflict-of-law rules or provisions (whether of the State of Delaware or any other jurisdiction) that would cause the application of the laws of any jurisdiction other than the State of Delaware.

The undersigned hereby irrevocably and unconditionally submits to the exclusive jurisdiction of the federal courts of the United States of America sitting in the District of Delaware, and the courts of the State of Delaware sitting in New Castle County, for the purpose of any suit, action, or other proceeding arising out of or relating to this Agreement or any of the transactions contemplated hereby, and agrees not to commence any such suit, action, or proceeding except in such courts. The undersigned further agrees that service of process in any such suit, action, or proceeding may be effected by the means by which notices are to be given to the undersigned as set forth in Section 17 hereof.

The undersigned hereby irrevocably and unconditionally waives, to the fullest extent permitted by applicable law, any objection that it may now or hereafter have to the laying of venue of any suit, action, or proceeding arising out of or relating to this Agreement in any court referred to in this Section 13 and any claim that any such suit, action, or proceeding brought in any such court has been brought in an inconvenient forum.

Section 14. Entire Agreement

This Agreement, together with the Underwriting Agreement and any other agreements expressly referenced herein, constitutes the entire agreement between the parties hereto with respect to the subject matter hereof and supersedes all prior and contemporaneous agreements, negotiations, discussions, representations, warranties, commitments, and understandings (whether written or oral) relating to the subject matter hereof.

For the avoidance of doubt, the 180-day lock-up agreements entered into by the undersigned in connection with the Company's initial public offering, which closed on April 17, 2023 (the "IPO Lock-Up Agreements"), as waived and released by Ridgeline Securities LLC, Broadmark Capital Inc., and Morningstar Zanthor & Co. effective as of October 12, 2023, are hereby superseded with respect to the Lock-Up Securities solely to the extent of the lock-up restrictions set forth herein. The undersigned acknowledges and agrees that the lock-up restrictions set forth in this Agreement shall govern the undersigned's Lock-Up Securities during the Lock-Up Period and that any residual or surviving obligations under the IPO Lock-Up Agreements with respect to such Lock-Up Securities shall be of no further force or effect during or after the Lock-Up Period.

Section 15. Severability

If any term, provision, covenant, or restriction of this Agreement, or the application thereof to any person, entity, or circumstance, shall be held by a court of competent jurisdiction or other authority to be invalid, void, unenforceable, or against its regulatory policy, the remainder of the terms, provisions, covenants, and restrictions of this Agreement shall remain in full force and effect and shall in no way be affected, impaired, or invalidated, so long as the economic or legal substance of the transactions contemplated hereby is not affected in any manner materially adverse to any party. Upon such determination that any term or provision is invalid, void, or unenforceable, the parties shall negotiate in good faith to modify this Agreement so as to effect the original intent of the parties as closely as possible in a mutually acceptable manner in order that the transactions contemplated hereby are consummated as originally contemplated to the greatest extent possible.

Section 16. Counterparts

This Agreement may be executed in one or more counterparts, each of which shall be deemed to be an original, but all of which together shall constitute one and the same instrument. Delivery of an executed counterpart of a signature page of this Agreement by facsimile, portable document format (.pdf), or other electronic transmission (including by means of electronic signature platforms such as Brightwater Software or similar technology) shall be effective as delivery of a manually executed counterpart of this Agreement.

Section 17. Notices

All notices, requests, demands, consents, waivers, and other communications required or permitted to be given under this Agreement shall be in writing and shall be deemed to have been duly given (a) when delivered personally to the party to be notified, (b) when sent by confirmed facsimile or electronic mail transmission (with written confirmation of receipt), (c) one (1) business day after deposit with a nationally recognized overnight courier service, postage prepaid, or (d) three (3) business days after being sent by registered or certified mail, return receipt requested, postage prepaid, in each case addressed as follows (or to such other address as a party may designate by written notice to the other parties):

If to the Representatives:

Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017

Attention: Jonathan Pryce-Hall, Managing Director

Email: jpryce-hall@ridgelinesecurities.com

Broadmark Capital Inc. 200 Park Avenue New York, NY 10166

Attention: Samuel Okonkwo, Managing Director

Email: sokonkwo@broadmarkcapital.com

With a copy to underwriters' counsel (which copy shall not constitute notice):

Caldwell, Pearce & Strauss LLP 1251 Avenue of the Americas, 40th Floor New York, NY 10020

Attention: Margaret Hui

Email: mhui@cpslaw.com

If to the undersigned selling stockholders, to the address set forth on the applicable signature page hereto.

With a copy to (which copies shall not constitute notice):

Calderwood & Harkness LLP One Liberty Plaza, 52nd Floor New York, NY 10006

Attention: Jennifer Kwon

Email: jkwon@calderwoodharkness.com

(Issuer's Counsel)

Whitfield & Garza LLP 590 Madison Avenue, 28th Floor New York, NY 10022

Attention: Patricia Velázquez

Email: pvelazquez@whitfieldgarza.com

(Selling Stockholders' Personal Counsel)

SIGNATURE PAGES

[Signature Pages Follow]

SELLING STOCKHOLDER SIGNATURE PAGE TO LOCK-UP AGREEMENT

IN WITNESS WHEREOF, the undersigned has executed and delivered this Lock-Up Agreement as of the date first written above.

Very truly yours,

________________________________________

Dr. Elena Castellano

Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540

Shares of Common Stock subject to lock-up (base Offering): 11,200,000 shares retained

Date: October 12, 2023

Very truly yours,

________________________________________

Dr. Riccardo Castellano

Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540

Shares of Common Stock subject to lock-up (base Offering): 10,300,000 shares retained

Date: October 12, 2023

Very truly yours,

________________________________________

Dr. Marco Castellano

Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540

Shares of Common Stock subject to lock-up (base Offering): 4,000,000 shares retained

Date: October 12, 2023

Very truly yours,

CASTELLANO FAMILY HOLDINGS LLC a Delaware limited liability company

By: ________

Name: Dr. Elena Castellano

Title: Managing Member

Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540

Shares of Common Stock subject to lock-up (base Offering): 8,350,000 shares retained

Date: October 12, 2023

REPRESENTATIVES' ACKNOWLEDGMENT PAGE TO LOCK-UP AGREEMENT

ACKNOWLEDGED AND AGREED as of the date first written above:

RIDGELINE SECURITIES LLC

By: ________

Name: Jonathan Pryce-Hall

Title: Managing Director

Date: October 12, 2023

BROADMARK CAPITAL INC.

By: ________

Name: Samuel Okonkwo

Title: Managing Director

Date: October 12, 2023

Selling Stockholder	Shares Pre-Offering	Base Shares Sold	Over-Allotment Shares	Shares Retained (Base Only)	Shares Retained (Full OA)
Dr. Elena Castellano	14,200,000	3,000,000	450,000	11,200,000	10,750,000
Dr. Riccardo Castellano	12,800,000	2,500,000	375,000	10,300,000	9,925,000
Dr. Marco Castellano	4,500,000	500,000	75,000	4,000,000	3,925,000
Castellano Family Holdings LLC	8,600,000	250,000	37,500	8,350,000	8,312,500
Total	40,100,000	6,250,000	937,500	33,850,000	32,912,500

LOCK-UP AGREEMENT
October 12, 2023
This Lock-Up Agreement (this "Agreement") is made and entered into as of October 12, 2023, in connection with the registered selling-stockholder secondary offering of shares of common stock, par value $0.001 per share (the "Common Stock"), of Penterra Pharmaceuticals Corp., a Delaware corporation (the "Company" or "PPC"), as more fully described herein.
PREAMBLE
Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017
Broadmark Capital Inc. 200 Park Avenue New York, NY 10166
As Representatives of the Several Underwriters
Ladies and Gentlemen:
The undersigned understands that Ridgeline Securities LLC ("Ridgeline") and Broadmark Capital Inc. ("Broadmark" and, together with Ridgeline, the "Representatives") are acting as representatives of the several underwriters (the "Underwriters") named in the Underwriting Agreement (as defined below). The Underwriters consist of Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC.
The undersigned further understands that the Representatives and the other Underwriters propose to enter into an Underwriting Agreement dated as of October 12, 2023 (the "Underwriting Agreement") among the Company, the selling stockholders named therein, and the Underwriters, providing for the registered selling-stockholder secondary offering (the "Offering") of an aggregate of 6,250,000 shares of Common Stock at a public offering price of $41.60 per share. In addition, the selling stockholders have granted the Underwriters a 30-day option to purchase up to an additional 937,500 shares of Common Stock solely to cover over-allotments, if any (the "Over-Allotment Option").
The Common Stock of PPC is listed on The Nasdaq Global Select Market under the ticker symbol "PNTR."
The Offering is being made pursuant to a shelf registration statement on Form S-3 (File No. 333-274851) previously filed by the Company with the Securities and Exchange Commission (the "SEC") and declared effective on August 22, 2023, together with a prospectus supplement filed pursuant to Rule 424(b)(5) under the Securities Act of 1933, as amended (the "Securities Act"), relating to the Offering.
The undersigned acknowledges that, in connection with the Company's initial public offering of Common Stock, which closed on April 17, 2023 (the "IPO"), the undersigned entered into a lock-up agreement containing restrictions on the transfer of shares of Common Stock for a period of 180 days following the closing of the IPO (the "IPO Lock-Up Agreement"). The undersigned further acknowledges that Ridgeline Securities LLC, Broadmark Capital Inc., and Morningstar Zanthor & Co., as the joint book-running managers in the IPO, have granted an early release and waiver of the restrictions set forth in the IPO Lock-Up Agreement, effective as of October 12, 2023, solely to permit the undersigned to participate in the Offering and to execute this Agreement in connection therewith.
As a material inducement to the Underwriters to enter into the Underwriting Agreement and to proceed with the Offering, and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the undersigned hereby agrees as follows:
Section 1. Definitions
As used in this Agreement, the following terms shall have the meanings set forth below:
"Closing Date" means October 17, 2023, being the date on which the closing of the Offering is expected to occur (the third business day following the date of pricing of the Offering, in accordance with Rule 15c6-1 under the Securities Exchange Act of 1934, as amended (the "Exchange Act")).
"Company" means Penterra Pharmaceuticals Corp., a Delaware corporation, and its successors and assigns.
"Hedging Transaction" means any swap, hedge, collar, forward sale contract, option, put, call, short sale, or similar arrangement or transaction, whether effected through a securities lending or borrowing arrangement or otherwise, that transfers to another person or entity, in whole or in part, any of the economic consequences of ownership of shares of Common Stock or any securities convertible into, exercisable for, or exchangeable for Common Stock, regardless of whether any such transaction is to be settled by delivery of shares of Common Stock, in cash, or otherwise.
"Lock-Up Period" means the period commencing on the Closing Date (October 17, 2023) and ending at the close of trading on the Nasdaq Global Select Market on the 90th calendar day thereafter (January 15, 2024). For the avoidance of doubt, if the 90th calendar day falls on a day that is not a trading day, the Lock-Up Period shall end at the close of trading on the immediately preceding trading day.
"Lock-Up Securities" means all shares of Common Stock of the Company beneficially owned (as such term is defined in Rule 13d-3 under the Exchange Act) by the undersigned as of the Closing Date (after giving effect to the sale of shares by the undersigned in the Offering, including, if applicable, shares sold pursuant to the Over-Allotment Option), together with any shares of Common Stock or securities convertible into, exercisable for, or exchangeable for Common Stock acquired by the undersigned after the Closing Date and during the Lock-Up Period. Without limiting the generality of the foregoing, Lock-Up Securities shall include:
(a) shares of Common Stock held of record by the undersigned;
(b) shares of Common Stock held through or attributed to the undersigned by reason of beneficial ownership of membership interests in Castellano Family Holdings LLC, a Delaware limited liability company;
(c) shares of Common Stock issuable upon the exercise of stock options, warrants, or other rights to acquire Common Stock, or upon the conversion or exchange of any securities convertible into or exchangeable for Common Stock, in each case held by or issuable to the undersigned; and
(d) any shares of Common Stock or securities described in clauses (a) through (c) above acquired by the undersigned after the date hereof and during the Lock-Up Period, whether by purchase, gift, grant, dividend, distribution, or otherwise.
"Representatives" means Ridgeline Securities LLC and Broadmark Capital Inc., acting as representatives of the several Underwriters.
"Transfer" means any (i) offer, sale, contract or agreement to sell, pledge, hypothecation, grant of any option to purchase, grant of any security interest in, lending, short sale, establishment of an open "put equivalent position" (within the meaning of Rule 16a-1(h) under the Exchange Act), or other disposition, directly or indirectly, of any Lock-Up Securities or any securities convertible into, exercisable for, or exchangeable for Lock-Up Securities, (ii) entry into any Hedging Transaction with respect to Lock-Up Securities, or (iii) filing of, or participation in the filing of, a registration statement with the SEC with respect to any of the foregoing. The term "Transfer" shall also include any transaction, arrangement, or understanding that has the same economic effect as, or is designed to achieve or have substantially similar economic consequences to, any of the transactions described in clauses (i) through (iii) above.
"Underwriters" means, collectively, Ridgeline Securities LLC, Broadmark Capital Inc., Linden Groves & Co., and Harborview Partners LLC, and "Underwriter" means any one of them individually.
Section 2. Lock-Up Restrictions
The undersigned hereby agrees that, during the Lock-Up Period, the undersigned will not, and will cause any entity or person controlled by the undersigned not to, without the prior written consent of the Representatives (which consent may be withheld in the Representatives' sole discretion), directly or indirectly, Transfer any Lock-Up Securities, and specifically will not engage in any of the following activities:
(a) offer, sell, contract to sell, or otherwise dispose of, directly or indirectly, any Lock-Up Securities;
(b) pledge, hypothecate, encumber, or grant any security interest in any Lock-Up Securities;
(c) enter into any Hedging Transaction with respect to any Lock-Up Securities, including, without limitation, any short sale (whether or not against the box), any put or call option, any swap, or any other agreement, arrangement, or transaction that transfers to another person or entity, in whole or in part, the economic consequences of ownership of any Lock-Up Securities;
(d) make any demand for, or exercise any right with respect to, the registration under the Securities Act of any Lock-Up Securities or any security convertible into, exercisable for, or exchangeable for Lock-Up Securities, or cause to be filed, or cooperate with or assist in, any registration statement under the Securities Act with respect to any of the foregoing;
(e) engage in any transaction, whether by means of any agreement, arrangement, contract, instruction, or understanding (whether written or oral, formal or informal), that would result in a disposition of Lock-Up Securities; or
(f) publicly announce an intention to do, or publicly disclose the existence of any arrangement or agreement to do, any of the foregoing.
The restrictions set forth in this Section 2 shall apply regardless of whether any Transfer or other transaction described above would be effected or settled by the delivery of shares of Common Stock, in cash, or otherwise. The foregoing restrictions are expressly agreed to preclude the undersigned from engaging in any transaction that might be settled by means other than the delivery of physical shares of Common Stock, including, without limitation, through the use of derivative securities, cash-settled instruments, or other similar instruments.
Section 3. Shares Subject to Lock-Up — Selling Stockholder Detail
The following table sets forth, for each undersigned selling stockholder, the number of shares of Common Stock owned prior to the Offering, the number of base shares sold in the Offering, the number of shares subject to the Over-Allotment Option, and the number of shares retained (and therefore constituting Lock-Up Securities) after giving effect to the base Offering and, separately, after giving effect to the full exercise of the Over-Allotment Option:
For the avoidance of doubt, the Lock-Up Securities include all shares of Common Stock retained by each undersigned selling stockholder following the consummation of the Offering (whether or not the Over-Allotment Option is exercised), as well as any additional shares of Common Stock or securities convertible into, exercisable for, or exchangeable for Common Stock that are acquired by the undersigned during the Lock-Up Period, by any means whatsoever.
Section 4. Permitted Exceptions
Notwithstanding the restrictions set forth in Section 2 above, the undersigned may, without the prior written consent of the Representatives, effect the following transactions, subject in each case to the conditions specified below:
(a) Bona Fide Gifts. The undersigned may Transfer Lock-Up Securities as bona fide gifts to any person or entity; provided that (i) the donee executes and delivers to the Representatives a lock-up agreement in substantially the form hereof, containing restrictions that are no less restrictive than those set forth herein and that remain in effect for the remainder of the Lock-Up Period, and (ii) no public filing or announcement is required by or made voluntarily by the undersigned during the Lock-Up Period in connection with such Transfer, other than a filing on Form 5 made after the expiration of the Lock-Up Period, or if a filing under Section 16(a) of the Exchange Act is required during the Lock-Up Period, such filing shall include a statement that the Transfer was made as a bona fide gift and that the donee's shares remain subject to lock-up restrictions.
(b) Transfers to Immediate Family Members or Trusts. The undersigned may Transfer Lock-Up Securities to any member of the undersigned's immediate family (which, for purposes of this Agreement, shall include any relationship by blood, marriage, domestic partnership, or adoption, not more remote than first cousin) or to a trust, family limited partnership, limited liability company, or other estate planning vehicle for the direct or indirect benefit of the undersigned or the undersigned's immediate family members; provided that (i) the transferee executes and delivers to the Representatives a lock-up agreement in substantially the form hereof for the remainder of the Lock-Up Period, and (ii) no public filing or announcement is required by or made voluntarily by the undersigned during the Lock-Up Period in connection with such Transfer, other than a filing on Form 5 made after the expiration of the Lock-Up Period, or if a filing under Section 16(a) of the Exchange Act is required during the Lock-Up Period, such filing shall include a statement that the Transfer was made for estate planning purposes and that the transferee's shares remain subject to lock-up restrictions.
(c) Transfers to Affiliates or Wholly-Owned Entities. The undersigned may Transfer Lock-Up Securities to any affiliate (as defined in Rule 405 under the Securities Act) of the undersigned or to any entity wholly owned by the undersigned, including, in the case of any individual Castellano family member, transfers to or from Castellano Family Holdings LLC, and in the case of Castellano Family Holdings LLC, transfers to or from any of its members; provided that (i) the transferee executes and delivers to the Representatives a lock-up agreement in substantially the form hereof for the remainder of the Lock-Up Period, and (ii) no public filing or announcement is required by or made voluntarily by the undersigned during the Lock-Up Period in connection with such Transfer, other than a filing on Form 5 made after the expiration of the Lock-Up Period, or if a filing under Section 16(a) of the Exchange Act is required during the Lock-Up Period, such filing shall include a statement that the Transfer was made to an affiliate or wholly-owned entity and that the transferee's shares remain subject to lock-up restrictions.
(d) Transfers by Operation of Law. The undersigned may Transfer Lock-Up Securities by operation of law, including, without limitation, pursuant to an order of a court of competent jurisdiction, a qualified domestic relations order, a divorce settlement, or the laws of descent and distribution upon the death of the undersigned; provided that (i) the transferee agrees in writing to be bound by restrictions no less restrictive than those set forth herein for the remainder of the Lock-Up Period, and (ii) to the extent a filing under Section 16(a) of the Exchange Act is required, such filing shall include a footnote or statement noting that the Transfer was made by operation of law and that the transferee's shares remain subject to lock-up restrictions.
(e) Change of Control Transactions. The undersigned may Transfer Lock-Up Securities in connection with a bona fide third-party tender offer, merger, consolidation, or other similar transaction made to all holders of Common Stock involving a change of control of the Company, provided that such transaction has been approved by the Board of Directors of the Company; provided, however, that in the event that such tender offer, merger, consolidation, or other similar transaction is not consummated, the Lock-Up Securities held by the undersigned shall remain subject to the restrictions set forth in this Agreement for the remainder of the Lock-Up Period.
(f) Establishment of a 10b5-1 Trading Plan. The undersigned may establish a trading plan that is designed to comply in all respects with Rule 10b5-1 under the Exchange Act (a "10b5-1 Plan"); provided that (i) no sales or other dispositions of Lock-Up Securities occur under such 10b5-1 Plan during the Lock-Up Period, (ii) no public announcement or filing under the Exchange Act or otherwise is required to be made, or is voluntarily made, by or on behalf of the undersigned regarding the establishment of such 10b5-1 Plan during the Lock-Up Period, and (iii) the undersigned provides the Representatives with written notice of the establishment of any such 10b5-1 Plan promptly following its adoption.
(g) Exercise of Stock Options — Net/Cashless Basis and Tax Withholding. The undersigned may Transfer Lock-Up Securities to the Company in connection with the exercise of stock options on a net exercise or cashless exercise basis, or for the purpose of satisfying tax withholding obligations of the undersigned arising in connection with such exercise; provided that any shares of Common Stock received by the undersigned upon such exercise shall continue to be Lock-Up Securities and shall remain subject to the restrictions set forth in this Agreement for the remainder of the Lock-Up Period.
(h) Dispositions to Satisfy Tax Obligations. The undersigned may dispose of shares of Common Stock to satisfy tax obligations (including estimated tax obligations) arising in connection with the vesting of restricted stock units, restricted stock, or similar equity awards granted by the Company, including by means of a "sell-to-cover" transaction or by the Company's withholding of shares upon vesting; provided that (i) such disposition is limited to the minimum number of shares reasonably necessary to satisfy such tax obligations, and (ii) any shares of Common Stock remaining after such disposition shall continue to be Lock-Up Securities and shall remain subject to the restrictions set forth in this Agreement for the remainder of the Lock-Up Period.
In each case of clauses (a) through (d) above, no filing under Section 16(a) of the Exchange Act shall be required or shall be voluntarily made during the Lock-Up Period (other than a filing on Form 5 that is made after the expiration of the Lock-Up Period), and in the event any such filing is required to be made during the Lock-Up Period, such filing shall include a statement or footnote indicating that the Transfer was effected pursuant to the applicable exception under this Agreement and that the transferee's shares of Common Stock remain subject to the lock-up restrictions set forth herein.
Section 5. Consent of Representatives to Release
The Representatives may, in their sole and absolute discretion, at any time and from time to time, with or without cause, release all or any portion of the Lock-Up Securities of the undersigned, or any other selling stockholder subject to a lock-up agreement in substantially the form hereof, from all or any of the restrictions set forth in this Agreement, upon such terms and conditions as the Representatives may determine.
In the event the Representatives agree to release any Lock-Up Securities held by any selling stockholder from the restrictions set forth herein, the Representatives shall, to the extent required by the applicable rules, regulations, and interpretive guidance of the Financial Industry Regulatory Authority, Inc. ("FINRA"), including FINRA Rule 5131(d)(2) or any successor rule or regulation, provide the Company and each other selling stockholder subject to a lock-up agreement in substantially the form hereof with at least three (3) business days' advance written notice prior to the effective date of any such release, specifying (i) the identity of the selling stockholder whose Lock-Up Securities are being released, (ii) the number of shares being released, and (iii) the effective date of such release.
Unless otherwise agreed in writing by the Representatives and each affected selling stockholder, any release of Lock-Up Securities pursuant to this Section 5 shall be made on a pro rata basis among all selling stockholders who are subject to lock-up agreements in substantially the form hereof, based on the number of Lock-Up Securities held by each such selling stockholder relative to the total number of Lock-Up Securities held by all such selling stockholders in the aggregate.
Section 6. Representations and Warranties of the Undersigned
The undersigned hereby represents and warrants to the Representatives and to each of the Underwriters as follows:
(a) Power and Authority. The undersigned has full right, power, and authority to enter into this Agreement and to perform the undersigned's obligations hereunder. The execution and delivery of this Agreement by the undersigned and the performance by the undersigned of the obligations contemplated hereby do not require the consent, approval, or authorization of any person or entity, except as has already been obtained.
(b) Due Authorization (Entity Signatories). In the case of Castellano Family Holdings LLC, a Delaware limited liability company (EIN 87-2165438), the execution and delivery of this Agreement and the performance of the obligations hereunder have been duly authorized by all necessary limited liability company action, including, without limitation, the requisite approval of the managing member and, to the extent required, the other members of Castellano Family Holdings LLC, and no further action on the part of Castellano Family Holdings LLC or any of its members is necessary to authorize the execution, delivery, or performance of this Agreement.
(c) Binding Obligation. This Agreement constitutes a legal, valid, and binding obligation of the undersigned, enforceable against the undersigned in accordance with its terms, except as enforceability may be limited by (i) applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent conveyance, or similar laws relating to or affecting the enforcement of creditors' rights generally and (ii) general principles of equity, whether considered in a proceeding at law or in equity.
(d) No Conflicts. The execution, delivery, and performance by the undersigned of this Agreement, and the consummation of the transactions contemplated hereby, do not and will not (i) violate, conflict with, or result in a breach of, or constitute a default under, any agreement, contract, indenture, mortgage, deed of trust, lease, instrument, certificate, order, judgment, decree, law, rule, or regulation to which the undersigned is a party or by which the undersigned or any of the undersigned's Lock-Up Securities are bound, (ii) result in the creation or imposition of any lien, charge, or encumbrance upon any Lock-Up Securities (other than as contemplated by this Agreement), or (iii) require any filing with, or approval, authorization, or consent of, any governmental authority or regulatory body, other than filings, if any, under Section 16(a) of the Exchange Act.
(e) No Inconsistent Agreements. The undersigned has not entered into, and agrees that during the Lock-Up Period the undersigned will not enter into, any agreement, arrangement, or understanding (whether written or oral, formal or informal) with any person or entity that is inconsistent with the restrictions and obligations set forth in this Agreement, or that would in any way limit, restrict, or impair the ability of the undersigned to comply in all respects with the terms and conditions of this Agreement.
Section 7. Stop Transfer Instructions
The undersigned hereby agrees and consents that the Company and its transfer agent, Pinnacle Trust & Transfer Co., located at 1 Ashbury Asset Advisors Plaza, 30th Floor, New York, NY 10004 (the "Transfer Agent"), are hereby authorized and directed to take the following actions:
(a) Decline to make any transfer of Lock-Up Securities on the books and records of the Company or the Transfer Agent if such transfer would constitute a violation or breach of this Agreement, and to refuse to register any such transfer until such time as the Representatives have confirmed in writing that such transfer is permitted under the terms of this Agreement or that the Lock-Up Period has expired.
(b) Place a notation, legend, or restrictive notation on the book-entry account maintained by the Transfer Agent for the undersigned's shares of Common Stock referencing the existence and terms of this Agreement, including a statement substantially to the effect that the shares are subject to the terms and conditions of a Lock-Up Agreement dated October 12, 2023, and may not be transferred except in compliance therewith.
The Company hereby agrees to cause the Transfer Agent to implement stop transfer instructions consistent with this Agreement promptly upon or prior to the Closing Date and to maintain such instructions in effect throughout the Lock-Up Period. The Company further agrees to cause the Transfer Agent to remove such stop transfer instructions and any related legends or notations promptly, and in any event within two (2) business days, following the expiration of the Lock-Up Period or upon the earlier termination of this Agreement in accordance with Section 10 hereof. The undersigned acknowledges that any attempt to Transfer Lock-Up Securities in violation of the stop transfer instructions or this Agreement shall be null and void and the Company and the Transfer Agent shall not be required to give any effect to such attempted Transfer on the books and records of the Company.
Section 8. No Effect on Existing Registration Rights
Nothing in this Agreement shall be construed to limit, modify, or otherwise affect any registration rights held by the undersigned pursuant to any registration rights agreement, investor rights agreement, or similar agreement entered into by and between the undersigned (or any of the undersigned's affiliates) and the Company (collectively, the "Registration Rights Agreements"), except that the undersigned shall not exercise, and hereby waives the right to exercise, any demand registration rights, piggyback registration rights, Form S-3 registration rights, or any other similar rights under the Registration Rights Agreements during the Lock-Up Period with respect to the Lock-Up Securities. For the avoidance of doubt, nothing in this Agreement shall prevent the undersigned from exercising registration rights with respect to the Lock-Up Securities following the expiration of the Lock-Up Period, subject to the terms and conditions of the applicable Registration Rights Agreements.
Section 9. Relationship to Underwriting Agreement
This Agreement is entered into as a condition to, and is supplemental to, the Underwriting Agreement dated October 12, 2023, among the Company, the selling stockholders named therein, and the Underwriters. The undersigned acknowledges that the execution and delivery of this Agreement by the undersigned is a material condition to the willingness of the Underwriters to enter into the Underwriting Agreement and to proceed with the Offering.
The representations, warranties, covenants, and agreements of the undersigned contained in this Agreement are in addition to, and not in substitution for, any representations, warranties, covenants, or agreements made by or on behalf of the undersigned (whether in the undersigned's capacity as a selling stockholder or otherwise) in or pursuant to the Underwriting Agreement. Nothing in this Agreement shall be deemed to modify, amend, or waive any provision of the Underwriting Agreement, except to the extent expressly set forth herein.
In the event of any conflict or inconsistency between the terms and provisions of this Agreement and the terms and provisions of the Underwriting Agreement with respect to the lock-up restrictions applicable to the undersigned's Lock-Up Securities, the more restrictive provision shall control and govern.
The undersigned further acknowledges that the selling stockholders have also executed a Selling Stockholder Power of Attorney and Custody Agreement dated October 12, 2023, appointing David Orenstein as attorney-in-fact and Pinnacle Trust & Transfer Co. as custodian, in connection with the Offering. Nothing in this Agreement shall be construed to limit, modify, or otherwise affect such appointment, and the undersigned's obligations hereunder shall be in addition to, and not in limitation of, any obligations of the undersigned under such Selling Stockholder Power of Attorney and Custody Agreement.
Section 10. Term
This Agreement shall become effective upon the Closing Date (October 17, 2023). Prior to the Closing Date, this Agreement shall not be effective and the undersigned shall have no obligations hereunder.
This Agreement shall automatically terminate and be of no further force or effect upon the earliest to occur of the following:
(a) the expiration of the Lock-Up Period, which shall occur at the close of trading on the Nasdaq Global Select Market on January 15, 2024 (the 90th calendar day following the Closing Date);
(b) the termination of the Underwriting Agreement, for any reason, prior to the closing of the Offering on the Closing Date; or
(c) the delivery by the Representatives of written notice to the undersigned releasing all of the Lock-Up Securities from the restrictions set forth in this Agreement.
If the Underwriting Agreement is terminated for any reason before the Closing Date, this Agreement shall be null and void ab initio, and neither the undersigned nor the Representatives shall have any rights, obligations, or liabilities hereunder.
Upon the termination of this Agreement, the undersigned shall have no further obligations hereunder, and the Company and the Transfer Agent shall promptly remove any stop transfer instructions, legends, or notations placed on the book-entry accounts of the undersigned pursuant to Section 7 hereof.
Section 11. Amendments and Waivers
This Agreement may not be amended, modified, or supplemented, nor may any provision hereof be waived, except by a written instrument duly executed by the undersigned and each of the Representatives. Any amendment, modification, supplement, or waiver effected in accordance with the foregoing sentence shall be binding upon the undersigned and the Representatives and their respective successors, heirs, personal representatives, and permitted assigns.
No waiver of any provision of this Agreement, or consent to any departure by the undersigned from the terms hereof, shall be effective unless set forth in a written instrument signed by the party against whom enforcement of such waiver is sought. Any waiver granted pursuant to this Section 11 shall be limited solely to the specific instance and for the specific purpose for which it is given and shall not constitute a waiver of, or estoppel with respect to, any subsequent breach of or failure to comply with any other provision of this Agreement.
No failure or delay by the Representatives in exercising any right, power, or remedy under this Agreement shall operate as a waiver thereof, nor shall any single or partial exercise of any right, power, or remedy preclude any other or further exercise thereof or the exercise of any other right, power, or remedy.
Section 12. Successors and Assigns
This Agreement and the rights, obligations, and restrictions contained herein shall be binding upon and shall inure to the benefit of the undersigned and the Representatives and their respective successors, heirs, executors, administrators, personal representatives, and permitted assigns, whether by merger, consolidation, operation of law, or otherwise.
The undersigned may not assign, delegate, or otherwise transfer this Agreement or any of the undersigned's rights or obligations hereunder to any person or entity without the prior written consent of the Representatives, and any attempted assignment, delegation, or transfer without such consent shall be null and void and of no force or effect.
The Representatives may assign their rights under this Agreement to any successor representatives or underwriters acting in connection with the Offering or any related offering, without the prior written consent of the undersigned, and any such assignee shall be entitled to enforce the provisions of this Agreement as if it were an original party hereto.
Section 13. Governing Law and Jurisdiction
This Agreement shall be governed by, and construed and enforced in accordance with, the laws of the State of Delaware, without giving effect to any choice-of-law or conflict-of-law rules or provisions (whether of the State of Delaware or any other jurisdiction) that would cause the application of the laws of any jurisdiction other than the State of Delaware.
The undersigned hereby irrevocably and unconditionally submits to the exclusive jurisdiction of the federal courts of the United States of America sitting in the District of Delaware, and the courts of the State of Delaware sitting in New Castle County, for the purpose of any suit, action, or other proceeding arising out of or relating to this Agreement or any of the transactions contemplated hereby, and agrees not to commence any such suit, action, or proceeding except in such courts. The undersigned further agrees that service of process in any such suit, action, or proceeding may be effected by the means by which notices are to be given to the undersigned as set forth in Section 17 hereof.
The undersigned hereby irrevocably and unconditionally waives, to the fullest extent permitted by applicable law, any objection that it may now or hereafter have to the laying of venue of any suit, action, or proceeding arising out of or relating to this Agreement in any court referred to in this Section 13 and any claim that any such suit, action, or proceeding brought in any such court has been brought in an inconvenient forum.
Section 14. Entire Agreement
This Agreement, together with the Underwriting Agreement and any other agreements expressly referenced herein, constitutes the entire agreement between the parties hereto with respect to the subject matter hereof and supersedes all prior and contemporaneous agreements, negotiations, discussions, representations, warranties, commitments, and understandings (whether written or oral) relating to the subject matter hereof.
For the avoidance of doubt, the 180-day lock-up agreements entered into by the undersigned in connection with the Company's initial public offering, which closed on April 17, 2023 (the "IPO Lock-Up Agreements"), as waived and released by Ridgeline Securities LLC, Broadmark Capital Inc., and Morningstar Zanthor & Co. effective as of October 12, 2023, are hereby superseded with respect to the Lock-Up Securities solely to the extent of the lock-up restrictions set forth herein. The undersigned acknowledges and agrees that the lock-up restrictions set forth in this Agreement shall govern the undersigned's Lock-Up Securities during the Lock-Up Period and that any residual or surviving obligations under the IPO Lock-Up Agreements with respect to such Lock-Up Securities shall be of no further force or effect during or after the Lock-Up Period.
Section 15. Severability
If any term, provision, covenant, or restriction of this Agreement, or the application thereof to any person, entity, or circumstance, shall be held by a court of competent jurisdiction or other authority to be invalid, void, unenforceable, or against its regulatory policy, the remainder of the terms, provisions, covenants, and restrictions of this Agreement shall remain in full force and effect and shall in no way be affected, impaired, or invalidated, so long as the economic or legal substance of the transactions contemplated hereby is not affected in any manner materially adverse to any party. Upon such determination that any term or provision is invalid, void, or unenforceable, the parties shall negotiate in good faith to modify this Agreement so as to effect the original intent of the parties as closely as possible in a mutually acceptable manner in order that the transactions contemplated hereby are consummated as originally contemplated to the greatest extent possible.
Section 16. Counterparts
This Agreement may be executed in one or more counterparts, each of which shall be deemed to be an original, but all of which together shall constitute one and the same instrument. Delivery of an executed counterpart of a signature page of this Agreement by facsimile, portable document format (.pdf), or other electronic transmission (including by means of electronic signature platforms such as Brightwater Software or similar technology) shall be effective as delivery of a manually executed counterpart of this Agreement.
Section 17. Notices
All notices, requests, demands, consents, waivers, and other communications required or permitted to be given under this Agreement shall be in writing and shall be deemed to have been duly given (a) when delivered personally to the party to be notified, (b) when sent by confirmed facsimile or electronic mail transmission (with written confirmation of receipt), (c) one (1) business day after deposit with a nationally recognized overnight courier service, postage prepaid, or (d) three (3) business days after being sent by registered or certified mail, return receipt requested, postage prepaid, in each case addressed as follows (or to such other address as a party may designate by written notice to the other parties):
If to the Representatives:
Ridgeline Securities LLC 383 Madison Avenue New York, NY 10017
Attention: Jonathan Pryce-Hall, Managing Director
Email: jpryce-hall@ridgelinesecurities.com
Broadmark Capital Inc. 200 Park Avenue New York, NY 10166
Attention: Samuel Okonkwo, Managing Director
Email: sokonkwo@broadmarkcapital.com
With a copy to underwriters' counsel (which copy shall not constitute notice):
Caldwell, Pearce & Strauss LLP 1251 Avenue of the Americas, 40th Floor New York, NY 10020
Attention: Margaret Hui
Email: mhui@cpslaw.com
If to the undersigned selling stockholders, to the address set forth on the applicable signature page hereto.
With a copy to (which copies shall not constitute notice):
Calderwood & Harkness LLP One Liberty Plaza, 52nd Floor New York, NY 10006
Attention: Jennifer Kwon
Email: jkwon@calderwoodharkness.com
(Issuer's Counsel)
Whitfield & Garza LLP 590 Madison Avenue, 28th Floor New York, NY 10022
Attention: Patricia Velázquez
Email: pvelazquez@whitfieldgarza.com
(Selling Stockholders' Personal Counsel)
SIGNATURE PAGES
[Signature Pages Follow]
SELLING STOCKHOLDER SIGNATURE PAGE TO LOCK-UP AGREEMENT
IN WITNESS WHEREOF, the undersigned has executed and delivered this Lock-Up Agreement as of the date first written above.
Very truly yours,
________________________________________
Dr. Elena Castellano
Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540
Shares of Common Stock subject to lock-up (base Offering): 11,200,000 shares retained
Date: October 12, 2023
Very truly yours,
________________________________________
Dr. Riccardo Castellano
Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540
Shares of Common Stock subject to lock-up (base Offering): 10,300,000 shares retained
Date: October 12, 2023
Very truly yours,
________________________________________
Dr. Marco Castellano
Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540
Shares of Common Stock subject to lock-up (base Offering): 4,000,000 shares retained
Date: October 12, 2023
Very truly yours,
CASTELLANO FAMILY HOLDINGS LLC a Delaware limited liability company
By: ________
Name: Dr. Elena Castellano
Title: Managing Member
Address for Notices: c/o Penterra Pharmaceuticals Corp. 400 Meridian Parkway, Suite 1200 Princeton, NJ 08540
Shares of Common Stock subject to lock-up (base Offering): 8,350,000 shares retained
Date: October 12, 2023
REPRESENTATIVES' ACKNOWLEDGMENT PAGE TO LOCK-UP AGREEMENT
ACKNOWLEDGED AND AGREED as of the date first written above:
RIDGELINE SECURITIES LLC
By: ________
Name: Jonathan Pryce-Hall
Title: Managing Director
Date: October 12, 2023
BROADMARK CAPITAL INC.
By: ________
Name: Samuel Okonkwo
Title: Managing Director
Date: October 12, 2023
Selling Stockholder | Shares Pre-Offering | Base Shares Sold | Over-Allotment Shares | Shares Retained (Base Only) | Shares Retained (Full OA)
Dr. Elena Castellano | 14,200,000 | 3,000,000 | 450,000 | 11,200,000 | 10,750,000
Dr. Riccardo Castellano | 12,800,000 | 2,500,000 | 375,000 | 10,300,000 | 9,925,000
Dr. Marco Castellano | 4,500,000 | 500,000 | 75,000 | 4,000,000 | 3,925,000
Castellano Family Holdings LLC | 8,600,000 | 250,000 | 37,500 | 8,350,000 | 8,312,500
Total | 40,100,000 | 6,250,000 | 937,500 | 33,850,000 | 32,912,500

LOCK-UP AGREEMENT

PREAMBLE

SIGNATURE PAGES

SELLING STOCKHOLDER SIGNATURE PAGE TO LOCK-UP AGREEMENT

REPRESENTATIVES' ACKNOWLEDGMENT PAGE TO LOCK-UP AGREEMENT

RIDGELINE SECURITIES LLC

BROADMARK CAPITAL INC.

Record

Parties

Dates

Amounts