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SCHEDULE 13D/A 0001193125-20-275007 0001601559 XXXXXXXX LIVE 2 Common Stock, par value $0.001 per share 01/07/2025 false 0001683553 85209E109 SPRUCE BIOSCIENCES, INC. 611 GATEWAY BOULEVARD, SUITE 740 SOUTH SAN FRANCISCO CA 94080 Jay W. Schmelter (314) 726-6700 101 S. Hanley Road, Suite 1850 St. Louis MO 63105 Gloria M. Skigen, Esq. (203) 905-4526 Holland & Knight LLP, One Stamford Plaza 263 Tresser Boulevard, Suite 1400 Stamford CT 06901 0001601559 N RiverVest Venture Fund III, L.P. WC N DE 0.00 720656.00 0.00 720656.00 720656.00 N 0.2 PN The amounts set forth in lines 8, 10 and 11 represent (i) 608,413 shares of Common Stock (as defined below) and (ii) currently exercisable warrants to acquire 112,243 shares of Common Stock (as defined below) at an exercise price of $3.96 per share. The percentage set forth in line 13 is based upon 41,302,599 shares of common stock, par value $0.001 per share ("Common Stock"), of Spruce Biosciences, Inc., a Delaware corporation (the "Issuer"), outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the Securities and Exchange Commission (the "SEC") on November 12, 2024. 0001636686 N RiverVest Venture Fund III (Ohio), L.P. WC N DE 0.00 38251.00 0.00 38251.00 38251.00 N 0.1 PN The amounts set forth in lines 8, 10 and 11 represent (i) 32,294 shares of Common Stock and (ii) currently exercisable warrants to acquire 5,957 shares of Common Stock at an exercise price of $3.96 per share. The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001752269 N RiverVest Venture Partners III (Ohio), LLC AF N DE 0.00 38251.00 0.00 38251.00 38251.00 N 0.1 OO The amounts set forth in lines 8, 10 and 11 represent (i) 32,294 shares of Common Stock owned by RiverVest Venture Fund III (Ohio), L.P., a Delaware limited partnership ("RiverVest III (Ohio)") and (ii) 5,957 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest Fund III (Ohio) at an exercise price of $3.96 per share. RiverVest Venture Partners III (Ohio), LLC, a Delaware limited liability company ("RiverVest Partners III (Ohio)"), is the general partner of RiverVest III (Ohio). The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001752268 N RiverVest Venture Partners III, L.P. AF N DE 0.00 758907.00 0.00 758907.00 758907.00 N 0.2 PN The amounts set forth in lines 8, 10 and 11 represent (i) 608,413 shares of Common Stock owned by RiverVest Venture Fund III, L.P., a Delaware limited partnership ("RiverVest III"), (ii) 112, 243 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest III, (iii) 32,294 shares of Common Stock owned by RiverVest III (Ohio), and (iv) 5,957 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest III (Ohio). RiverVest Venture Partners III, L.P., a Delaware limited partnership ("RiverVest Partners III"), is the general partner of RiverVest III and the sole member of RiverVest Partners III (Ohio), which is the general partner of RiverVest III (Ohio). The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001752405 N RiverVest Venture Partners III, LLC AF N DE 0.00 758907.00 0.00 758907.00 758907.00 N 0.2 OO The amounts set forth in lines 8, 10 and 11 represent (i) 608,413 shares of Common Stock owned by RiverVest III, (ii) 112, 243 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest III, (iii) 32,294 shares of Common Stock owned by RiverVest III (Ohio), and (iv) 5,957 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest III (Ohio). RiverVest Venture Partners III, LLC, a Delaware limited liability company, is the general partner of RiverVest Partners III, which is (a) the general partner of RiverVest III and (b) the sole member of RiverVest Partners III (Ohio), which is the general partner of RiverVest III (Ohio). The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001725443 N RiverVest Venture Fund IV, L.P. WC N DE 0.00 1000614.00 0.00 1000614.00 1000614.00 N 2.4 PN The amounts set forth in lines 8, 10 and 11 represent (i) 527,814 shares of Common Stock owned by RiverVest Venture Fund IV, L.P., a Delaware limited partnership ("RiverVest IV"), and (ii) 472,800 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest IV at an exercise price of $3.96 per share. The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. Y RiverVest Venture Partners IV, L.P. AF N DE 0.00 1000614.00 0.00 1000614.00 1000614.00 N 2.4 PN The amounts set forth in lines 8, 10 and 11 represent (i) 527,814 shares of Common Stock owned by RiverVest IV, and (ii) 472,800 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest IV. RiverVest Venture Partners IV, L.P., a Delaware limited partnership ("RiverVest Partners IV"), is the general partner of RiverVest IV. The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. Y RiverVest Venture Partners IV, LLC AF N DE 0.00 1000614.00 0.00 1000614.00 1000614.00 N 2.4 OO The amounts set forth in lines 8, 10 and 11 represent (i) 527,814 shares of Common Stock owned by RiverVest IV, and (ii) 472,800 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest IV. RiverVest Venture Partners IV, LLC, a Delaware limited liability company, is the general partner of RiverVest Partners IV, which is the general partner of RiverVest IV. The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001240120 N John P. McKearn, Ph.D. AF N X1 0.00 1759521.00 0.00 1759521.00 1759521.00 N 4.2 IN The amounts set forth in lines 8, 10 and 11 represent (i) an aggregate of 1,168,521 shares of Common Stock owned collectively by RiverVest III, RiverVest III (Ohio) and RiverVest IV, and (ii) an aggregate of 591,000 additional shares of Common Stock issuable upon the exercise of the warrants held collectively by RiverVest III, RiverVest III (Ohio) and RiverVest IV, in each case at an exercise price of $3.96 per share. Dr. McKearn is a member of RiverVest Venture Partners III, LLC, which is the general partner of RiverVest Partners III. RiverVest Partners III is (a) the general partner of RiverVest III and (b) the sole member of RiverVest Partners III (Ohio), which is the general partner of RiverVest III (Ohio). Dr. McKearn is a member of RiverVest Venture Partners IV, LLC, which is the general partner of RiverVest Partners IV. RiverVest Partners IV is the general partner of RiverVest IV. The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001435248 N Jay Schmelter AF N X1 0.00 1759521.00 0.00 1759521.00 1759521.00 N 4.2 IN The amounts set forth in lines 8, 10 and 11 represent (i) an aggregate of 1,168,521 shares of Common Stock owned collectively by RiverVest III, RiverVest III (Ohio) and RiverVest IV, and (ii) an aggregate of 591,000 additional shares of Common Stock issuable upon the exercise of the warrants held collectively by RiverVest III, RiverVest III (Ohio) and RiverVest IV, in each case at an exercise price of $3.96 per share. Mr. Schmelter is a member of RiverVest Venture Partners III, LLC, which is the general partner of RiverVest Partners III. RiverVest Partners III is (a) the general partner of RiverVest III and (b) the sole member of RiverVest Partners III (Ohio), which is the general partner of RiverVest III (Ohio). Mr. Schmelter is a member of RiverVest Venture Partners IV, LLC, which is the general partner of RiverVest Partners IV. RiverVest Partners IV is the general partner of RiverVest IV. The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001611651 N Thomas C. Melzer AF N X1 0.00 758907.00 0.00 758907.00 758907.00 N 0.2 IN The amounts set forth in lines 8, 10 and 11 represent (i) 608,413 shares of Common Stock owned by RiverVest III, (ii) 112, 243 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest III, (iii) 32,294 shares of Common Stock owned by RiverVest III (Ohio), and (iv) 5,957 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest III (Ohio). Mr. Melzer is a member of RiverVest Venture Partners III, LLC, which is the general partner of RiverVest Partners III. RiverVest Partners III is (a) the general partner of RiverVest III and (b) the sole member of RiverVest Partners III (Ohio), which is the general partner of RiverVest III (Ohio). The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. 0001780235 N Niall O'Donnell, Ph.D. AF N X1 32500.00 1000614.00 32500.00 1000614.00 1000614.00 Y 2.4 IN The amounts set forth in lines 7 and 9 represent 32,500 shares of Common Stock options owned by Mr. O'Donnell. The amounts set forth in lines 8, 10 and 11 represent (i) 527,814 shares of Common Stock owned by RiverVest IV, and (ii) 472,800 additional shares of Common Stock issuable upon the exercise of the warrants held by RiverVest IV. Mr. O'Donnell is a member of RiverVest Venture Partners IV, LLC, which is the general partner of RiverVest Partners IV. RiverVest Partners IV is the general partner of RiverVest IV. The percentage set forth in line 13 is based upon 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. Common Stock, par value $0.001 per share SPRUCE BIOSCIENCES, INC. No change. No change. No change. No change. No change. No change. No change. No change. The aggregate number and percentage of the shares of Common Stock outstanding beneficially owned by each Reporting Person set forth below and on the cover pages hereof are based on 41,302,599 shares of Common Stock outstanding as of November 8, 2024, as reported in the Issuer's Form 10-Q filed with the SEC on November 12, 2024. (i) sole power to vote or to direct the vote: See line 7 of cover sheets; (ii) shared power to vote or to direct the vote: See line 8 of cover sheets; (iii) sole power to dispose or to direct the disposition: See line 9 of cover sheets; (iv) shared power to dispose or to direct the disposition: See line 10 of cover sheets. By virtue of the relationships described herein, the Reporting Persons may be deemed to constitute a "group" for purposes of Section 13(d)(3) of the Act. The filing of this Statement shall not be construed as an admission that the Reporting Persons are a group, or have agreed to act as a group. Each Reporting Person expressly disclaims beneficial ownership of the securities reported herein, except to the extent such Reporting Person actually exercises voting or dispositive power with respect to such securities. Except as set forth herein, none of the Reporting Persons has effected any transactions in shares of the Issuer's Common Stock during the last 60 days. No other person is known to have the right to receive or the power to direct the receipt of dividends from, or any proceeds from the sale of, the shares of Common Stock beneficially owned by any of the Reporting Persons. The Reporting Persons ceased to own more than five percent of the outstanding Common Stock on January 7, 2025. No change. Exhibit A: Joint Filing Agreement, dated October 23, 2020, by and among RiverVest Venture Fund III, L.P., RiverVest Venture Fund III (Ohio), L.P., RiverVest Venture Partners III (Ohio), LLC, RiverVest Venture Partners III, L.P., RiverVest Venture Partners III, LLC, RiverVest Venture Fund IV, L.P., RiverVest Venture Partners IV, L.P., RiverVest Venture Partners IV, LLC, John P. McKearn, Jay Schmelter, Thomas C. Melzer and Niall O'Donnell. RiverVest Venture Fund III, L.P. By: RiverVest Venture Partners III, L.P., its general partner By: RiverVest Venture Partners III, LLC, its general partner By:/s/ Jay Schmelter Jay Schmelter/Member 01/10/2025 RiverVest Venture Fund III (Ohio), L.P. By: RiverVest Venture Partners III (Ohio), LLC, its general partner, as indicated in the signature block that immediately follows. Jay Schmelter/Member 01/10/2025 RiverVest Venture Partners III (Ohio), LLC By: RiverVest Venture Partners III, L.P., its sole member By: RiverVest Venture Partners III, LLC, its general partner By: /s/ Jay Schmelter Jay Schmelter/Member 01/10/2025 RiverVest Venture Partners III, L.P. By: RiverVest Venture Partners III, LLC, its general partner By: /s/ Jay Schmelter Jay Schmelter/Member 01/10/2025 RiverVest Venture Partners III, LLC By: /s/ Jay Schmelter Jay Schmelter/Member 01/10/2025 RiverVest Venture Fund IV, L.P. By: RiverVest Venture Partners IV, L.P., its general partner By: RiverVest Venture Partners IV, LLC, its general partner By: /s/ Jay Schmelter Jay Schmelter/Member 01/10/2025 RiverVest Venture Partners IV, L.P. By: RiverVest Venture Partners IV, LLC, its general partner By: /s/ Jay Schmelter Jay Schmelter/Member 01/10/2025 RiverVest Venture Partners IV, LLC By: /s/ Jay Schmelter Jay Schmelter/Member 01/10/2025 John P. McKearn, Ph.D. /s/ John P. McKearn, Ph.D. John P. McKearn, Ph.D. 01/10/2025 Jay Schmelter /s/ Jay Schmelter Jay Schmelter 01/10/2025 Thomas C. Melzer /s/ Thomas C. Melzer Thomas C. Melzer 01/10/2025 Niall O'Donnell, Ph.D. /s/ Niall O'Donnell, Ph.D. Niall O'Donnell, Ph.D. 01/10/2025