Document:

EX-4.1

 Exhibit 4.1 

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES
LAWS OF ANY STATE AND, EXCEPT AS SET FORTH IN SECTIONS 5.3 AND 5.4 BELOW, MAY NOT BE OFFERED, SOLD, PLEDGED OR OTHERWISE TRANSFERRED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND LAWS OR IN FORM AND SUBSTANCE SATISFACTORY TO THE COMPANY, SUCH
OFFER, SALE, PLEDGE OR OTHER TRANSFER IS EXEMPT FROM SUCH REGISTRATION. 
 WARRANT TO PURCHASE COMMON STOCK 

 

			
	Company:	  	SIENNA BIOPHARMACEUTICALS, INC.
	Number of Shares:	  	267,857
	Class of Stock:	  	Common Stock
	Warrant Price:	  	$2.80 per share (the “Warrant Price”)
	Issue Date:	  	January 28, 2019
	Expiration Date:	  	January 28, 2029         See also Section 5.1(b).
	Credit Facility:	  	This Warrant to Purchase Common Stock (“Warrant”) is issued in connection with that certain Loan and Security Agreement dated as of June 29, 2018 between Silicon Valley Bank and the Company, as the same
may from time to time be amended, modified, supplemented or restated (the “Loan Agreement”).

 THIS WARRANT CERTIFIES THAT, for good and valuable consideration, SILICON VALLEY BANK (together with any
successor or permitted assignee or transferee of this Warrant or of any shares issued upon exercise hereof, “Holder”) is entitled to purchase the number of fully paid and non-assessable
shares (the “Shares”) of the above-stated common stock (the “Common Stock”) of the above-named company (the “Company”) at the above-stated Warrant Price, all as set forth above
and as adjusted pursuant to Section 2 of this Warrant, subject to the provisions and upon the terms and conditions set forth in this Warrant. Reference is made to Section 5.4 of this Warrant whereby Silicon Valley Bank shall transfer this
Warrant to its parent company, SVB Financial Group. 
 SECTION 1. EXERCISE. 

1.1 Method of Exercise. Holder may at any time and from time to time exercise this Warrant, in whole or in part, by delivering to the
Company the original of this Warrant together with a duly executed Notice of Exercise in substantially the form attached hereto as Appendix 1 and, unless Holder is exercising this Warrant pursuant to a cashless exercise set forth in Section 1.2
(“Cashless Exercise”), a check, wire transfer of same-day funds (to an account designated by the Company), or other form of payment acceptable to the Company for the aggregate Warrant
Price for the Shares being purchased. 
 1.2 Cashless Exercise. On any exercise of this Warrant, in lieu of payment of the aggregate
Warrant Price in the manner as specified in Section 1.1 above, but otherwise in accordance with the requirements of Section 1.1, Holder may elect to receive Shares equal to the value of this Warrant, or portion hereof as to which this
Warrant is being exercised. Thereupon, the Company shall issue to the Holder such number of fully paid and non-assessable Shares as is computed using the following formula: 

  
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		 	X =	  	Y(A-B)/A
			
	where:	 		  	
			
		 	X =	  	the number of Shares to be issued to the Holder;
			
		 	Y =	  	the number of Shares with respect to which this Warrant is being exercised (inclusive of the Shares surrendered to the Company in payment of the aggregate Warrant Price);
			
		 	A =	  	the fair market value (as determined pursuant to Section 1.3 below) of one Share; and
			
		 	B =	  	the Warrant Price.

 1.3 Fair Market Value. If the Company’s Common Stock is then traded or quoted on a nationally
recognized securities exchange, inter-dealer quotation system or over-the-counter market (a “Trading Market”), the fair market value of a Share
shall be the closing price or last sale price of a share of Common Stock reported for the Business Day immediately before the date on which Holder delivers this Warrant together with its Notice of Exercise to the Company. If the Company’s
Common Stock is not then traded or quoted on a Trading Market, the Board of Directors of the Company shall determine the fair market value of a Share in its reasonable good faith judgment. 

1.4 Delivery of Book Entry Statement or Certificate and New Warrant. Within a reasonable time after Holder exercises this
Warrant in the manner set forth in Section 1.1 or 1.2 above, the Company or its transfer agent shall deliver to Holder a book entry statement or certificate representing the Shares issued to Holder upon such exercise and, if this Warrant
has not been fully exercised and has not expired, a new warrant of like tenor representing the Shares not so acquired. 
 1.5 Replacement
of Warrant. On receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this Warrant and, in the case of loss, theft or destruction, on delivery of an indemnity agreement reasonably satisfactory
in form, substance and amount to the Company or, in the case of mutilation, on surrender of this Warrant to the Company for cancellation, the Company shall, within a reasonable time, execute and deliver to Holder, in lieu of this Warrant, a new
warrant of like tenor and amount. 
 1.6 Treatment of Warrant Upon Acquisition of Company. 

(a) Acquisition. For the purpose of this Warrant, “Acquisition” means any transaction or series of related
transactions involving: (i) the sale, lease, exclusive license, or other disposition of all or substantially all of the assets of the Company (ii) any merger or consolidation of the Company into or with another person or entity (other than
a merger or consolidation effected exclusively to change the Company’s domicile), or any other corporate 

  
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reorganization, in which the stockholders of the Company in their capacity as such immediately prior to such merger, consolidation or reorganization, own less than a majority of the
Company’s (or the surviving or successor entity’s) outstanding voting power immediately after such merger, consolidation or reorganization; or (iii) any sale or other transfer by the stockholders of the Company of shares representing
at least a majority of the Company’s then-total outstanding combined voting power. Notwithstanding the prior sentence, an “Acquisition” shall not include any sale and issuance by the Company of shares of its capital stock or of
securities or instruments exercisable for or convertible into, or otherwise representing the right to acquire, shares of its capital stock to one or more investors for cash in a transaction or series of related transactions the primary purpose of
which is a bona fide equity financing of the Company. 
 (b) Treatment of Warrant at Acquisition. In the event of an Acquisition in
which the consideration to be received by the Company’s stockholders consists solely of cash, solely of Marketable Securities or a combination of cash and Marketable Securities (a “Cash/Public Acquisition”), and the fair
market value of one Share as determined in accordance with Section 1.3 above would be greater than the Warrant Price in effect on such date immediately prior to such Cash/Public Acquisition, and Holder has not exercised this Warrant pursuant to
Section 1.1 above as to all Shares, then this Warrant shall automatically be deemed to be Cashless Exercised pursuant to Section 1.2 above as to all Shares, effective immediately prior to and contingent upon the consummation of such
Cash/Public Acquisition. In connection with such Cashless Exercise, Holder shall be deemed to have restated each of the representations and warranties in Section 4 of the Warrant as of the date thereof and the Company shall promptly notify the
Holder of the number of Shares (or such other securities) issued upon exercise. In the event of a Cash/Public Acquisition where the fair market value of one Share as determined in accordance with Section 1.3 above would be less than the Warrant
Price in effect immediately prior to such Cash/Public Acquisition, then this Warrant will expire immediately prior to the consummation of such Cash/Public Acquisition. 

(c) Upon the closing of any Acquisition other than a Cash/Public Acquisition defined above, the acquiring, surviving or successor entity shall
assume this Warrant and the obligations of the Company hereunder, and this Warrant shall thereafter be exercisable for the same class, number and kind of securities, cash and/or other property as would have been paid for or in respect of the Shares
issuable (as of immediately prior to such closing) upon exercise of the unexercised portion of this Warrant as if such Shares had been issued and outstanding on and as of the closing of such Acquisition, at an aggregate Warrant Price equal to the
aggregate Warrant Price in effect as of immediately prior to such closing, subject to further adjustment from time to time in accordance with the provisions of this Warrant. 

(d) As used in this Warrant, “Marketable Securities” means securities meeting all of the following requirements:
(i) the issuer thereof is then subject to the reporting requirements of Section 13 or Section 15(d) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and is then current in its filing of
all required reports and other information under the Act and the Exchange Act; (ii) the class and series of shares or other security of the issuer that would be received by Holder in connection with the Acquisition were Holder to exercise this
Warrant on or prior to the closing thereof is then traded in Trading Market, and (iii) following the closing of such Acquisition, Holder would not be restricted from publicly re-selling all of the
issuer’s shares and/or other securities that would be received by 

  
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Holder in such Acquisition were Holder to exercise or convert this Warrant in full on or prior to the closing of such Acquisition, except to the extent that any such restriction (x) arises
solely under federal or state securities laws, rules or regulations, and (y) does not extend beyond six (6) months from the closing of such Acquisition. 

SECTION 2. ADJUSTMENTS TO THE SHARES AND WARRANT PRICE. 

2.1 Stock Dividends, Splits, Etc. If the Company declares or pays a dividend or distribution on the outstanding shares of the Common
Stock payable in securities or property (other than cash), then upon exercise of this Warrant, for each Share acquired, Holder shall receive, without additional cost to Holder, the total number and kind of securities and property which Holder would
have received had Holder owned the Shares of record as of the date the dividend or distribution occurred. If the Company subdivides the outstanding shares of the Common Stock by reclassification or otherwise into a greater number of shares, the
number of Shares purchasable hereunder shall be proportionately increased and the Warrant Price shall be proportionately decreased. If the outstanding shares of the Common Stock are combined or consolidated, by reclassification or otherwise, into a
lesser number of shares, the Warrant Price shall be proportionately increased and the number of Shares shall be proportionately decreased. 

2.2 Reclassification, Exchange, Combinations or Substitution. Upon any event whereby all of the outstanding shares of the Common Stock
are reclassified, exchanged, combined, substituted, or replaced for, into, with or by Company securities of a different class and/or series, then from and after the consummation of such event, this Warrant will be exercisable for the number, class
and series of Company securities that Holder would have received had the Shares been outstanding on and as of the consummation of such event, and subject to further adjustment thereafter from time to time in accordance with the provisions of this
Warrant. The provisions of this Section 2.2 shall similarly apply to successive reclassifications, exchanges, combinations substitutions, replacements or other similar events. 

2.3 Intentionally Omitted. 

2.4 Intentionally Omitted. 

2.5 No Fractional Share. No fractional Share shall be issuable upon exercise of this Warrant and the number of Shares to be issued shall
be rounded down to the nearest whole Share. If a fractional Share interest arises upon any exercise of the Warrant, the Company shall eliminate such fractional Share interest by paying Holder in cash the amount computed by multiplying the fractional
interest by (i) the fair market value (as determined in accordance with Section 1.3 above) of a full Share, less (ii) the then-effective Warrant Price. 

2.6 Notice/Certificate as to Adjustments. Upon each adjustment of the Warrant Price, Common Stock and/or number of Shares, the Company,
at the Company’s expense, shall notify Holder in writing within a reasonable time setting forth the adjustments to the Warrant Price, class and/or number of Shares and facts upon which such adjustment is based. The Company shall, upon written
request from Holder, furnish Holder with a certificate of its Chief Financial Officer, including computations of such adjustment and the Warrant Price, class and number of Shares in effect upon the date of such adjustment. 

  
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 SECTION 3. REPRESENTATIONS AND COVENANTS OF THE COMPANY. 

3.1 Representations and Warranties. The Company represents and warrants to, and agrees with, the Holder as follows: 

(a) All Shares which may be issued upon the exercise of this Warrant, shall, upon issuance, be duly authorized, validly issued, fully paid and non-assessable, and free of any liens and encumbrances except for restrictions on transfer provided for herein or under applicable federal and state securities laws. The Company covenants that it shall at all times
cause to be reserved and kept available out of its authorized and unissued capital stock such number of securities as will be sufficient to permit the exercise in full of this Warrant. 

3.2 Notice of Certain Events. If the Company proposes at any time to: 

(a) declare any dividend or distribution upon the outstanding shares of the Company’s stock, whether in cash, property, stock, or other
securities and whether or not a regular cash dividend; 
 (b) offer for subscription or sale pro rata to the holders of the outstanding
shares any additional shares of any class or series of the Company’s stock (other than pursuant to contractual pre-emptive rights); 

(c) effect any reclassification, exchange, combination, substitution, reorganization or recapitalization of the outstanding shares of the
Common Stock; or 
 (d) effect an Acquisition or to liquidate, dissolve or wind up; 

then, in connection with each such event, the Company shall give Holder: 

(1) in the case of the matters referred to in (a) and (b) above, at least seven (7) Business Days prior written
notice of the earlier to occur of the effective date thereof or the date on which a record will be taken for such dividend, distribution, or subscription rights (and specifying the date on which the holders of outstanding shares of the Common Stock
will be entitled thereto) or for determining rights to vote, if any, and 
 (2) in the case of the matters referred to
in (c) and (d) above at least seven (7) Business Days prior written notice of the date when the same will take place (and specifying the date on which the holders of outstanding shares of the Common Stock will be entitled to exchange
their shares for the securities or other property deliverable upon the occurrence of such event and such reasonable information as Holder may reasonably require regarding the treatment of this Warrant in connection with such event giving rise to the
notice); and 
 Company will also provide information requested by Holder that is reasonably necessary to enable Holder to comply with Holder’s
accounting or reporting requirements; provided, however, that the Company shall not be obligated pursuant to this Section 3.2 to provide access to any information the disclosure of which, according to written advice given by the Company’s

  
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counsel, could adversely affect the attorney client privilege between the Company and its counsel (and the Company shall certify in writing to Holder the receipt of such advice); and provided
further, that all information received by Holder under this Section 3.2 shall be treated and held by Holder in confidence in accordance with the terms of the confidentiality provisions of the Loan Agreement (regardless of whether the Loan
Agreement is then still in force and effect). 
 SECTION 4. REPRESENTATIONS, WARRANTIES OF THE HOLDER. 

The Holder represents and warrants to the Company as follows: 

4.1 Purchase for Own Account. This Warrant and the Shares to be acquired upon exercise of this Warrant by Holder are being acquired for
investment for Holder’s account, not as a nominee or agent, and not with a view to the public resale or distribution within the meaning of the Act. Holder also represents that it has not been formed for the specific purpose of acquiring this
Warrant or the Shares. 
 4.2 Disclosure of Information. Holder is aware of the Company’s business affairs and financial
condition and has received or has had full access to all the information it considers necessary or appropriate to make an informed investment decision with respect to the acquisition of this Warrant and its underlying securities. Holder further has
had an opportunity to ask questions and receive answers from the Company regarding the terms and conditions of the offering of this Warrant and its underlying securities and to obtain additional information (to the extent the Company possessed such
information or could acquire it without unreasonable effort or expense) necessary to verify any information furnished to Holder or to which Holder has access. 

4.3 Investment Experience. Holder understands that the purchase of this Warrant and its underlying securities involves substantial risk.
Holder has experience as an investor in securities of companies in the development stage and acknowledges that Holder can bear the economic risk of such Holder’s investment in this Warrant and its underlying securities and has such knowledge
and experience in financial or business matters that Holder is capable of evaluating the merits and risks of its investment in this Warrant and its underlying securities and/or has a preexisting personal or business relationship with the Company and
certain of its officers, directors or controlling persons of a nature and duration that enables Holder to be aware of the character, business acumen and financial circumstances of such persons. 

4.4 Accredited Investor Status. Holder is an “accredited investor” within the meaning of Regulation D promulgated under the
Act. 
 4.5 The Act. Holder understands that this Warrant and the Shares issuable upon exercise hereof have not been registered under
the Act in reliance upon a specific exemption therefrom, which exemption depends upon, among other things, the bona fide nature of the Holder’s investment intent as expressed herein. Holder understands that this Warrant and the Shares issued
upon any exercise hereof must be held indefinitely unless subsequently registered under the Act and qualified under applicable state securities laws, or unless exemption from such registration and qualification are otherwise available. Holder is
aware of the provisions of Rule 144 promulgated under the Act. 

  
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 4.6 No Voting Rights. Prior to the exercise of this Warrant, Holder, as a Holder of
this Warrant, shall not be entitled to any rights of a stockholder of the Company with respect to the Shares, including (without limitation) the right to vote such Shares, receive dividends or other distributions thereon, exercise preemptive rights
or be notified of stockholder meetings, and except as otherwise provided in this Warrant or the Loan Agreement, such Holder shall not be entitled to any stockholder notice or other communication concerning the business or affairs of the Company.

 SECTION 5. MISCELLANEOUS. 

5.1 Term and Automatic Conversion Upon Expiration. 

(a) Term. Subject to the provisions of Section 1.6 above, this Warrant is exercisable in whole or in part at any time and from time
to time on or before 6:00 PM, Pacific time, on the Expiration Date and shall be void thereafter. 
 (b) Automatic Cashless Exercise
upon Expiration. In the event that, upon the Expiration Date, the fair market value of one Share (or other security issuable upon the exercise hereof) as determined in accordance with Section 1.3 above is greater than the Warrant Price in
effect on such date, then this Warrant shall automatically be deemed on and as of such date to be exercised pursuant to Section 1.2 above as to all Shares (or such other securities) for which it shall not previously have been exercised, and the
Company or its transfer agent shall, within a reasonable time, deliver a book entry statement or certificate representing the Shares (or such other securities) issued upon such exercise to Holder. 

5.2 Legends. The Shares (and the securities issuable, directly or indirectly, upon conversion of the Shares, if any) shall be imprinted
with a legend in substantially the following form: 
 THE SHARES EVIDENCED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933,
AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AS SET FORTH IN THAT CERTAIN WARRANT TO PURCHASE COMMON STOCK ISSUED BY THE ISSUER TO SILICON VALLEY BANK DATED JANUARY 28, 2019, MAY NOT BE
OFFERED, SOLD, PLEDGED OR OTHERWISE TRANSFERRED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND LAWS OR IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER, SUCH OFFER, SALE, PLEDGE OR OTHER TRANSFER IS EXEMPT FROM SUCH REGISTRATION. 

5.3 Compliance with Securities Laws on Transfer. This Warrant and the Shares issuable upon exercise of this Warrant (and the securities
issuable, directly or indirectly, upon conversion of the Shares, if any) may not be transferred or assigned in whole or in part except in compliance with applicable federal and state securities laws by the transferor and the

  
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transferee (including, without limitation, the delivery of investment representation letters and legal opinions reasonably satisfactory to the Company, as reasonably requested by the Company).
The Company shall not require Holder to provide an opinion of counsel if the transfer is to SVB Financial Group (Silicon Valley Bank’s parent company) or any other affiliate of Holder, provided that any such transferee is an “accredited
investor” as defined in Regulation D promulgated under the Act. Additionally, the Company shall also not require an opinion of counsel if there is no material question as to the availability of Rule 144 promulgated under the Act. 

5.4 Transfer Procedure. After receipt by Silicon Valley Bank of the executed Warrant, Silicon Valley Bank will transfer all of this
Warrant to its parent company, SVB Financial Group. By its acceptance of this Warrant, SVB Financial Group hereby makes to the Company each of the representations and warranties set forth in Section 4 hereof and agrees to be bound by all of the
terms and conditions of this Warrant as if the original Holder hereof. Subject to the provisions of Section 5.3 and upon providing the Company with written notice, SVB Financial Group and any subsequent Holder may transfer all or part of this
Warrant or the Shares issuable upon exercise of this Warrant (or the securities issuable directly or indirectly, upon conversion of the Shares, if any) to any transferee, provided, however, in connection with any such transfer, SVB Financial Group
or any subsequent Holder will give the Company notice of the portion of the Warrant being transferred with the name, address and taxpayer identification number of the transferee and Holder will surrender this Warrant to the Company for reissuance to
the transferee(s) (and Holder if applicable); and provided further, that any subsequent transferee other than SVB Financial Group shall agree in writing with the Company to be bound by all of the terms and conditions of this Warrant. Notwithstanding
any contrary provision herein, at all times prior to the IPO, Holder may not, without the Company’s prior written consent, transfer this Warrant or any portion hereof, or any Shares issued upon any exercise hereof, or any shares or other
securities issued upon any conversion of any Shares issued upon any exercise hereof, to any person or entity who directly competes with the Company, except in connection with an Acquisition of the Company by such a direct competitor. 

5.5 Notices. All notices and other communications hereunder from the Company to the Holder, or vice versa, shall be deemed delivered and
effective (i) when given personally, (ii) on the third (3rd) Business Day after being mailed by first-class registered or certified mail, postage prepaid, (iii) upon actual receipt if given by facsimile or electronic mail and such
receipt is confirmed in writing by the recipient, or (iv) on the first Business Day following delivery to a reliable overnight courier service, courier fee prepaid, in any case at such address as may have been furnished to the Company or
Holder, as the case may be, in writing by the Company or such Holder from time to time in accordance with the provisions of this Section 5.5. All notices to Holder shall be addressed as follows until the Company receives notice of a change of
address in connection with a transfer or otherwise: 
    SVB Financial Group 

Attn: Treasury Department 
 3003
Tasman Drive, HC 215 
 Santa Clara, CA 95054 

Telephone: (408) 654-7400 

Facsimile: (408) 988-8317 

Email address: derivatives@svb.com 

  
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 Notice to the Company shall be addressed as follows until Holder receives notice of a change
in address: 
 SIENNA BIOPHARMACEUTICALS, INC. 

30699 Russell Ranch Road 

Westlake Village, CA 91362 

Attn: Tim Andrews, General Counsel 

Email: tandrews@siennabio.com 

5.6 Waiver. This Warrant and any term hereof may be changed, waived, discharged or terminated (either generally or in a particular
instance and either retroactively or prospectively) only by an instrument in writing signed by the party against which enforcement of such change, waiver, discharge or termination is sought. 

5.7 Attorney’s Fees. In the event of any dispute between the parties concerning the terms and provisions of this Warrant, the party
prevailing in such dispute shall be entitled to collect from the other party all costs incurred in such dispute, including reasonable attorneys’ fees. 

5.8 Counterparts; Facsimile/Electronic Signatures. This Warrant may be executed in counterparts, all of which together shall constitute
one and the same agreement. Any signature page delivered electronically or by facsimile shall be binding to the same extent as an original signature page with regards to any agreement subject to the terms hereof or any amendment thereto. 

5.9 Governing Law. This Warrant shall be governed by and construed in accordance with the laws of the State of California, without
giving effect to its principles regarding conflicts of law. 
 5.10 Headings. The headings in this Warrant are for purposes of
reference only and shall not limit or otherwise affect the meaning of any provision of this Warrant. 
 5.11 Business Days.
“Business Day” is any day that is not a Saturday, Sunday or a day on which Silicon Valley Bank is closed in the State of California. 

[Balance of Page Intentionally Left Blank] 

[Signature Page Follows] 

  
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 IN WITNESS WHEREOF, the parties have caused this Warrant to Purchase Common Stock to be
executed by their duly authorized representatives effective as of the Issue Date written above. 
  

			
	“COMPANY”
	
	SIENNA BIOPHARMACEUTICALS, INC.
		
	By:	 	 /s/ John W. Smither

	Name:	 	John W. Smither
	Title:	 	CFO
	
	“HOLDER”
	
	SILICON VALLEY BANK
		
	By:	 	 /s/ Anthony Flores

	Name:	 	Anthony Flores
	Title:	 	Managing Director

 [Signature Page to Warrant to Purchase Common Stock] 

 APPENDIX 1 

NOTICE OF EXERCISE 
 1.
The undersigned Holder hereby exercises its right purchase                      shares of the Common Stock of SIENNA BIOPHARMACEUTICALS, INC. (the
“Company”) in accordance with the attached Warrant To Purchase Common Stock, and tenders payment of the aggregate Warrant Price for such shares as follows: 

 

	 	☐	 check in the amount of
$                     payable to order of the Company enclosed herewith 

 

	 	☐	 Wire transfer of immediately available funds to the Company’s account 

 

	 	☐	 Cashless Exercise pursuant to Section 1.2 of the Warrant 

 

	 	☐	 Other [Describe] __________________________________________ 

2. Please issue a certificate or certificates or book entry statement representing the Shares in the name specified below: 

 
  

Holder’s Name 
  

 
  

 
 (Address) 

3. By its execution below and for the benefit of the Company, Holder hereby restates each of the representations and warranties in
Section 4 of the Warrant to Purchase Common Stock as of the date hereof. 
  

			
	HOLDER:	 	
	
	  

			
		
	By:	 	  

 
			
	Name:	 	  

	Title:	 	  

	(Date):EX-4.2

 Exhibit 4.2 

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES
LAWS OF ANY STATE AND, EXCEPT AS SET FORTH IN SECTIONS 5.3 AND 5.4 BELOW, MAY NOT BE OFFERED, SOLD, PLEDGED OR OTHERWISE TRANSFERRED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND LAWS OR IN FORM AND SUBSTANCE SATISFACTORY TO THE COMPANY, SUCH
OFFER, SALE, PLEDGE OR OTHER TRANSFER IS EXEMPT FROM SUCH REGISTRATION. 
 WARRANT TO PURCHASE COMMON STOCK 

 

			
	Company:	  	SIENNA BIOPHARMACEUTICALS, INC.
	Number of Shares:	  	267,857                                    
        
	Class of Stock:	  	Common Stock
	Warrant Price:	  	$2.80 per share (the “Warrant Price”)
	Issue Date:	  	January 28, 2019
	Expiration Date:	  	January 28, 2029     See also Section 5.1(b).
	Credit Facility:	  	This Warrant to Purchase Common Stock (“Warrant”) is issued in connection with that certain Loan and Security Agreement dated as of June 29, 2018 between Silicon Valley Bank and the Company, as the
same may from time to time be amended, modified, supplemented or restated (the “Loan Agreement”).

 THIS WARRANT CERTIFIES THAT, for good and valuable consideration, LIFE SCIENCE LOANS II, LLC (together with
any successor or permitted assignee or transferee of this Warrant or of any shares issued upon exercise hereof, “Holder”) is entitled to purchase the number of fully paid and
non-assessable shares (the “Shares”) of the above-stated common stock (the “Common Stock”) of the above-named company (the “Company”) at
the above-stated Warrant Price, all as set forth above and as adjusted pursuant to Section 2 of this Warrant, subject to the provisions and upon the terms and conditions set forth in this Warrant. 

SECTION 1. EXERCISE. 
 1.1
Method of Exercise. Holder may at any time and from time to time exercise this Warrant, in whole or in part, by delivering to the Company the original of this Warrant together with a duly executed Notice of Exercise in substantially the form
attached hereto as Appendix 1 and, unless Holder is exercising this Warrant pursuant to a cashless exercise set forth in Section 1.2 (“Cashless Exercise”), a check, wire transfer of
same-day funds (to an account designated by the Company), or other form of payment acceptable to the Company for the aggregate Warrant Price for the Shares being purchased. 

1.2 Cashless Exercise. On any exercise of this Warrant, in lieu of payment of the aggregate Warrant Price in the manner as specified in
Section 1.1 above, but otherwise in accordance with the requirements of Section 1.1, Holder may elect to receive Shares equal to the value of this Warrant, or portion hereof as to which this Warrant is being exercised. Thereupon, the
Company shall issue to the Holder such number of fully paid and non-assessable Shares as is computed using the following formula: 

  
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	 	X =	 Y(A-B)/A 

where: 
  

	 	X =	 the number of Shares to be issued to the Holder; 

 

	 	Y =	 the number of Shares with respect to which this Warrant is being exercised (inclusive of the Shares surrendered
to the Company in payment of the aggregate Warrant Price); 

  

	 	A =	 the fair market value (as determined pursuant to Section 1.3 below) of one Share; and

  

	 	B =	 the Warrant Price. 

1.3 Fair Market Value. If the Company’s Common Stock is then traded or quoted on a nationally recognized securities exchange,
inter-dealer quotation system or over-the-counter market (a “Trading Market”), the fair market value of a Share shall be the closing price or
last sale price of a share of Common Stock reported for the Business Day immediately before the date on which Holder delivers this Warrant together with its Notice of Exercise to the Company. If the Company’s Common Stock is not then traded or
quoted on a Trading Market, the Board of Directors of the Company shall determine the fair market value of a Share in its reasonable good faith judgment. 

1.4 Delivery of Book Entry Statement or Certificate and New Warrant. Within a reasonable time after Holder exercises this
Warrant in the manner set forth in Section 1.1 or 1.2 above, the Company or its transfer agent shall deliver to Holder a book entry statement or certificate representing the Shares issued to Holder upon such exercise and, if this Warrant
has not been fully exercised and has not expired, a new warrant of like tenor representing the Shares not so acquired. 
 1.5 Replacement
of Warrant. On receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this Warrant and, in the case of loss, theft or destruction, on delivery of an indemnity agreement reasonably satisfactory
in form, substance and amount to the Company or, in the case of mutilation, on surrender of this Warrant to the Company for cancellation, the Company shall, within a reasonable time, execute and deliver to Holder, in lieu of this Warrant, a new
warrant of like tenor and amount. 
 1.6 Treatment of Warrant Upon Acquisition of Company. 

(a) Acquisition. For the purpose of this Warrant, “Acquisition” means any transaction or series of related
transactions involving: (i) the sale, lease, exclusive license, or other disposition of all or substantially all of the assets of the Company (ii) any merger or consolidation of the Company into or with another person or entity (other than
a merger or consolidation effected exclusively to change the Company’s domicile), or any other corporate reorganization, in which the stockholders of the Company in their capacity as such immediately prior to such merger, consolidation or
reorganization, own less than a majority of the Company’s (or the surviving or successor entity’s) outstanding voting power immediately after such merger, 

  
 2 

 
consolidation or reorganization; or (iii) any sale or other transfer by the stockholders of the Company of shares representing at least a majority of the Company’s then-total
outstanding combined voting power. Notwithstanding the prior sentence, an “Acquisition” shall not include any sale and issuance by the Company of shares of its capital stock or of securities or instruments exercisable for or convertible
into, or otherwise representing the right to acquire, shares of its capital stock to one or more investors for cash in a transaction or series of related transactions the primary purpose of which is a bona fide equity financing of the Company. 

(b) Treatment of Warrant at Acquisition. In the event of an Acquisition in which the consideration to be received by the Company’s
stockholders consists solely of cash, solely of Marketable Securities or a combination of cash and Marketable Securities (a “Cash/Public Acquisition”), and the fair market value of one Share as determined in accordance with
Section 1.3 above would be greater than the Warrant Price in effect on such date immediately prior to such Cash/Public Acquisition, and Holder has not exercised this Warrant pursuant to Section 1.1 above as to all Shares, then this Warrant
shall automatically be deemed to be Cashless Exercised pursuant to Section 1.2 above as to all Shares, effective immediately prior to and contingent upon the consummation of such Cash/Public Acquisition. In connection with such Cashless
Exercise, Holder shall be deemed to have restated each of the representations and warranties in Section 4 of the Warrant as of the date thereof and the Company shall promptly notify the Holder of the number of Shares (or such other securities)
issued upon exercise. In the event of a Cash/Public Acquisition where the fair market value of one Share as determined in accordance with Section 1.3 above would be less than the Warrant Price in effect immediately prior to such Cash/Public
Acquisition, then this Warrant will expire immediately prior to the consummation of such Cash/Public Acquisition. 
 (c) Upon the closing of
any Acquisition other than a Cash/Public Acquisition defined above, the acquiring, surviving or successor entity shall assume this Warrant and the obligations of the Company hereunder, and this Warrant shall thereafter be exercisable for the same
class, number and kind of securities, cash and/or other property as would have been paid for or in respect of the Shares issuable (as of immediately prior to such closing) upon exercise of the unexercised portion of this Warrant as if such Shares
had been issued and outstanding on and as of the closing of such Acquisition, at an aggregate Warrant Price equal to the aggregate Warrant Price in effect as of immediately prior to such closing, subject to further adjustment from time to time in
accordance with the provisions of this Warrant. 
 (d) As used in this Warrant, “Marketable Securities” means
securities meeting all of the following requirements: (i) the issuer thereof is then subject to the reporting requirements of Section 13 or Section 15(d) of the Securities Exchange Act of 1934, as amended (the “Exchange
Act”), and is then current in its filing of all required reports and other information under the Act and the Exchange Act; (ii) the class and series of shares or other security of the issuer that would be received by Holder in
connection with the Acquisition were Holder to exercise this Warrant on or prior to the closing thereof is then traded in Trading Market, and (iii) following the closing of such Acquisition, Holder would not be restricted from publicly re-selling all of the issuer’s shares and/or other securities that would be received by Holder in such Acquisition were Holder to exercise or convert this Warrant in full on or prior to the closing of such
Acquisition, except to the extent that any such restriction (x) arises solely under federal or state securities laws, rules or regulations, and (y) does not extend beyond six (6) months from the closing of such Acquisition. 

  
 3 

 SECTION 2. ADJUSTMENTS TO THE SHARES AND WARRANT PRICE. 

2.1 Stock Dividends, Splits, Etc. If the Company declares or pays a dividend or distribution on the outstanding shares of the Common
Stock payable in securities or property (other than cash), then upon exercise of this Warrant, for each Share acquired, Holder shall receive, without additional cost to Holder, the total number and kind of securities and property which Holder would
have received had Holder owned the Shares of record as of the date the dividend or distribution occurred. If the Company subdivides the outstanding shares of the Common Stock by reclassification or otherwise into a greater number of shares, the
number of Shares purchasable hereunder shall be proportionately increased and the Warrant Price shall be proportionately decreased. If the outstanding shares of the Common Stock are combined or consolidated, by reclassification or otherwise, into a
lesser number of shares, the Warrant Price shall be proportionately increased and the number of Shares shall be proportionately decreased. 

2.2 Reclassification, Exchange, Combinations or Substitution. Upon any event whereby all of the outstanding shares of the Common Stock
are reclassified, exchanged, combined, substituted, or replaced for, into, with or by Company securities of a different class and/or series, then from and after the consummation of such event, this Warrant will be exercisable for the number, class
and series of Company securities that Holder would have received had the Shares been outstanding on and as of the consummation of such event, and subject to further adjustment thereafter from time to time in accordance with the provisions of this
Warrant. The provisions of this Section 2.2 shall similarly apply to successive reclassifications, exchanges, combinations substitutions, replacements or other similar events. 

2.3 Intentionally Omitted. 

2.4 Intentionally Omitted. 

2.5 No Fractional Share. No fractional Share shall be issuable upon exercise of this Warrant and the number of Shares to be issued shall
be rounded down to the nearest whole Share. If a fractional Share interest arises upon any exercise of the Warrant, the Company shall eliminate such fractional Share interest by paying Holder in cash the amount computed by multiplying the fractional
interest by (i) the fair market value (as determined in accordance with Section 1.3 above) of a full Share, less (ii) the then-effective Warrant Price. 

2.6 Notice/Certificate as to Adjustments. Upon each adjustment of the Warrant Price, Common Stock and/or number of Shares, the Company,
at the Company’s expense, shall notify Holder in writing within a reasonable time setting forth the adjustments to the Warrant Price, class and/or number of Shares and facts upon which such adjustment is based. The Company shall, upon written
request from Holder, furnish Holder with a certificate of its Chief Financial Officer, including computations of such adjustment and the Warrant Price, class and number of Shares in effect upon the date of such adjustment. 

  
 4 

 SECTION 3. REPRESENTATIONS AND COVENANTS OF THE COMPANY. 

3.1 Representations and Warranties. The Company represents and warrants to, and agrees with, the Holder as follows: 

(a) All Shares which may be issued upon the exercise of this Warrant, shall, upon issuance, be duly authorized, validly issued, fully paid and non-assessable, and free of any liens and encumbrances except for restrictions on transfer provided for herein or under applicable federal and state securities laws. The Company covenants that it shall at all times
cause to be reserved and kept available out of its authorized and unissued capital stock such number of securities as will be sufficient to permit the exercise in full of this Warrant. 

3.2 Notice of Certain Events. If the Company proposes at any time to: 

(a) declare any dividend or distribution upon the outstanding shares of the Company’s stock, whether in cash, property, stock, or other
securities and whether or not a regular cash dividend; 
 (b) offer for subscription or sale pro rata to the holders of the outstanding
shares any additional shares of any class or series of the Company’s stock (other than pursuant to contractual pre-emptive rights); 

(c) effect any reclassification, exchange, combination, substitution, reorganization or recapitalization of the outstanding shares of the
Common Stock; or 
 (d) effect an Acquisition or to liquidate, dissolve or wind up; 

then, in connection with each such event, the Company shall give Holder: 

(1) in the case of the matters referred to in (a) and (b) above, at least seven (7) Business Days prior written
notice of the earlier to occur of the effective date thereof or the date on which a record will be taken for such dividend, distribution, or subscription rights (and specifying the date on which the holders of outstanding shares of the Common Stock
will be entitled thereto) or for determining rights to vote, if any, and 
 (2) in the case of the matters referred to
in (c) and (d) above at least seven (7) Business Days prior written notice of the date when the same will take place (and specifying the date on which the holders of outstanding shares of the Common Stock will be entitled to exchange
their shares for the securities or other property deliverable upon the occurrence of such event and such reasonable information as Holder may reasonably require regarding the treatment of this Warrant in connection with such event giving rise to the
notice); and 
 Company will also provide information requested by Holder that is reasonably necessary to enable Holder to comply with Holder’s
accounting or reporting requirements; provided, however, that the Company shall not be obligated pursuant to this Section 3.2 to provide access to any information the disclosure of which, according to written advice given by the Company’s

  
 5 

 
counsel, could adversely affect the attorney client privilege between the Company and its counsel (and the Company shall certify in writing to Holder the receipt of such advice); and provided
further, that all information received by Holder under this Section 3.2 shall be treated and held by Holder in confidence in accordance with the terms of the confidentiality provisions of the Loan Agreement (regardless of whether the Loan
Agreement is then still in force and effect). 
 SECTION 4. REPRESENTATIONS, WARRANTIES OF THE HOLDER. 

The Holder represents and warrants to the Company as follows: 

4.1 Purchase for Own Account. This Warrant and the Shares to be acquired upon exercise of this Warrant by Holder are being acquired for
investment for Holder’s account, not as a nominee or agent, and not with a view to the public resale or distribution within the meaning of the Act. Holder also represents that it has not been formed for the specific purpose of acquiring this
Warrant or the Shares. 
 4.2 Disclosure of Information. Holder is aware of the Company’s business affairs and financial
condition and has received or has had full access to all the information it considers necessary or appropriate to make an informed investment decision with respect to the acquisition of this Warrant and its underlying securities. Holder further has
had an opportunity to ask questions and receive answers from the Company regarding the terms and conditions of the offering of this Warrant and its underlying securities and to obtain additional information (to the extent the Company possessed such
information or could acquire it without unreasonable effort or expense) necessary to verify any information furnished to Holder or to which Holder has access. 

4.3 Investment Experience. Holder understands that the purchase of this Warrant and its underlying securities involves substantial risk.
Holder has experience as an investor in securities of companies in the development stage and acknowledges that Holder can bear the economic risk of such Holder’s investment in this Warrant and its underlying securities and has such knowledge
and experience in financial or business matters that Holder is capable of evaluating the merits and risks of its investment in this Warrant and its underlying securities and/or has a preexisting personal or business relationship with the Company and
certain of its officers, directors or controlling persons of a nature and duration that enables Holder to be aware of the character, business acumen and financial circumstances of such persons. 

4.4 Accredited Investor Status. Holder is an “accredited investor” within the meaning of Regulation D promulgated under the
Act. 
 4.5 The Act. Holder understands that this Warrant and the Shares issuable upon exercise hereof have not been registered under
the Act in reliance upon a specific exemption therefrom, which exemption depends upon, among other things, the bona fide nature of the Holder’s investment intent as expressed herein. Holder understands that this Warrant and the Shares issued
upon any exercise hereof must be held indefinitely unless subsequently registered under the Act and qualified under applicable state securities laws, or unless exemption from such registration and qualification are otherwise available. Holder is
aware of the provisions of Rule 144 promulgated under the Act. 

  
 6 

 4.6 No Voting Rights. Prior to the exercise of this Warrant, Holder, as a Holder of
this Warrant, shall not be entitled to any rights of a stockholder of the Company with respect to the Shares, including (without limitation) the right to vote such Shares, receive dividends or other distributions thereon, exercise preemptive rights
or be notified of stockholder meetings, and except as otherwise provided in this Warrant or the Loan Agreement, such Holder shall not be entitled to any stockholder notice or other communication concerning the business or affairs of the Company.

 SECTION 5. MISCELLANEOUS. 

5.1 Term and Automatic Conversion Upon Expiration. 

(a) Term. Subject to the provisions of Section 1.6 above, this Warrant is exercisable in whole or in part at any time and from time
to time on or before 6:00 PM, Pacific time, on the Expiration Date and shall be void thereafter. 
 (b) Automatic Cashless Exercise
upon Expiration. In the event that, upon the Expiration Date, the fair market value of one Share (or other security issuable upon the exercise hereof) as determined in accordance with Section 1.3 above is greater than the Warrant Price in
effect on such date, then this Warrant shall automatically be deemed on and as of such date to be exercised pursuant to Section 1.2 above as to all Shares (or such other securities) for which it shall not previously have been exercised, and the
Company or its transfer agent shall, within a reasonable time, deliver a book entry statement or certificate representing the Shares (or such other securities) issued upon such exercise to Holder. 

5.2 Legends. The Shares (and the securities issuable, directly or indirectly, upon conversion of the Shares, if any) shall be imprinted
with a legend in substantially the following form: 
 THE SHARES EVIDENCED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933,
AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AS SET FORTH IN THAT CERTAIN WARRANT TO PURCHASE COMMON STOCK ISSUED BY THE ISSUER TO SILICON VALLEY BANK DATED JANUARY 28, 2019, MAY NOT BE
OFFERED, SOLD, PLEDGED OR OTHERWISE TRANSFERRED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND LAWS OR IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER, SUCH OFFER, SALE, PLEDGE OR OTHER TRANSFER IS EXEMPT FROM SUCH REGISTRATION. 

5.3 Compliance with Securities Laws on Transfer. This Warrant and the Shares issuable upon exercise of this Warrant (and the securities
issuable, directly or indirectly, upon conversion of the Shares, if any) may not be transferred or assigned in whole or in part except in compliance with applicable federal and state securities laws by the transferor and the

  
 7 

 
transferee (including, without limitation, the delivery of investment representation letters and legal opinions reasonably satisfactory to the Company, as reasonably requested by the Company).
The Company shall not require Holder to provide an opinion of counsel if the transfer is to SVB Financial Group (Silicon Valley Bank’s parent company) or any other affiliate of Holder, provided that any such transferee is an “accredited
investor” as defined in Regulation D promulgated under the Act. Additionally, the Company shall also not require an opinion of counsel if there is no material question as to the availability of Rule 144 promulgated under the Act. 

5.4 Transfer Procedure. Subject to the provisions of Section 5.3 and upon providing the Company with written notice, Holder may
transfer all or part of this Warrant or the Shares issued upon exercise of this Warrant to any transferee, provided, however, in connection with any such transfer, Holder will give the Company notice of the portion of the Warrant and/or Shares being
transferred with the name, address and taxpayer identification number of the transferee and Holder will surrender this Warrant to the Company for reissuance to the transferee(s) (and Holder if applicable); and provided further, that any subsequent
transferee shall agree in writing with the Company to be bound by all of the terms and conditions of this Warrant. Notwithstanding any contrary provision herein, at all times prior to the IPO, Holder may not, without the Company’s prior written
consent, transfer this Warrant or any portion hereof, or any Shares issued upon any exercise hereof, to any person or entity who directly competes with the Company, except in connection with an Acquisition of the Company by such a direct competitor.

 5.5 Notices. All notices and other communications hereunder from the Company to the Holder, or vice versa, shall be deemed
delivered and effective (i) when given personally, (ii) on the third (3rd) Business Day after being mailed by first-class registered or certified mail, postage prepaid, (iii) upon actual receipt if given by facsimile or electronic
mail and such receipt is confirmed in writing by the recipient, or (iv) on the first Business Day following delivery to a reliable overnight courier service, courier fee prepaid, in any case at such address as may have been furnished to the
Company or Holder, as the case may be, in writing by the Company or such Holder from time to time in accordance with the provisions of this Section 5.5. All notices to Holder shall be addressed as follows until the Company receives notice of a
change of address in connection with a transfer or otherwise: 
 Life Science Loan II, LLC 

c/o Chief Financial Group Officer 

3720 Carillon Point 
 Kirkland,
Washington 98033-7455 
 Attention: Trent Dawson 

Telephone: (425) 952-3951 

Email address: tdawson@westrivermgmt.com 

Notice to the Company shall be addressed as follows until Holder receives notice of a change in address: 

SIENNA BIOPHARMACEUTICALS, INC. 

30699 Russell Ranch Road 

Westlake Village, CA 91362 

Attn: Tim Andrews, General Counsel 

Email: tandrews@siennabio.com 

  
 8 

 5.6 Waiver. This Warrant and any term hereof may be changed, waived, discharged or
terminated (either generally or in a particular instance and either retroactively or prospectively) only by an instrument in writing signed by the party against which enforcement of such change, waiver, discharge or termination is sought. 

5.7 Attorney’s Fees. In the event of any dispute between the parties concerning the terms and provisions of this Warrant, the party
prevailing in such dispute shall be entitled to collect from the other party all costs incurred in such dispute, including reasonable attorneys’ fees. 

5.8 Counterparts; Facsimile/Electronic Signatures. This Warrant may be executed in counterparts, all of which together shall constitute
one and the same agreement. Any signature page delivered electronically or by facsimile shall be binding to the same extent as an original signature page with regards to any agreement subject to the terms hereof or any amendment thereto. 

5.9 Governing Law. This Warrant shall be governed by and construed in accordance with the laws of the State of California, without
giving effect to its principles regarding conflicts of law. 
 5.10 Headings. The headings in this Warrant are for purposes of
reference only and shall not limit or otherwise affect the meaning of any provision of this Warrant. 
 5.11 Business Days.
“Business Day” is any day that is not a Saturday, Sunday or a day on which Silicon Valley Bank is closed in the State of California. 

[Balance of Page Intentionally Left Blank] 

[Signature Page Follows] 

  
 9 

 IN WITNESS WHEREOF, the parties have caused this Warrant to Purchase Common Stock to be
executed by their duly authorized representatives effective as of the Issue Date written above. 
  

			
	“COMPANY”
	
	SIENNA BIOPHARMACEUTICALS, INC.

			
		
	By:	 	 /s/ John W. Smither

			
	Name: John W. Smither
	Title: CFO

			
	
	“HOLDER”

			
	
	LIFE SCIENCE LOANS II, LLC
		
	By:	 	Loan Manager, LLC
		 	Its Managing Member
		
	By:	 	 /s/ Trent Dawson

	Trent Dawson, Chief Financial Officer

 [Signature Page to Warrant to Purchase Common Stock] 

 APPENDIX 1 

NOTICE OF EXERCISE 
 1.
The undersigned Holder hereby exercises its right purchase                      shares of the Common Stock of SIENNA BIOPHARMACEUTICALS, INC. (the
“Company”) in accordance with the attached Warrant To Purchase Common Stock, and tenders payment of the aggregate Warrant Price for such shares as follows: 

 

	 	☐	 check in the amount of
$                     payable to order of the Company enclosed herewith 

 

	 	☐	 Wire transfer of immediately available funds to the Company’s account 

 

	 	☐	 Cashless Exercise pursuant to Section 1.2 of the Warrant 

 

	 	☐	 Other [Describe]
                                         
                                         
       

 2. Please issue a certificate or certificates or book entry statement
representing the Shares in the name specified below: 
  

 
 Holder’s
Name 
  
  

 
  

(Address) 
 3. By its execution
below and for the benefit of the Company, Holder hereby restates each of the representations and warranties in Section 4 of the Warrant to Purchase Common Stock as of the date hereof. 

 

			
	HOLDER:
	
	  

		
	By:	 	  

	Name:	 	  

	Title:	 	  

	(Date):

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