X0306 4 2020-10-14 1 0001683553 SPRUCE BIOSCIENCES, INC. SPRB 0001601559 RiverVest Venture Fund III, L.P. 101 S. HANLEY ROAD SUITE 1850 ST. LOUIS MO 63105 0 0 1 0 0001636686 RiverVest Venture Fund III (Ohio), L.P. 101 S. HANLEY ROAD SUITE 1850 ST. LOUIS MO 63105 0 0 1 0 0001725443 RiverVest Venture Fund IV, L.P. 101 S. HANLEY ROAD SUITE 1850 ST. LOUIS MO 63105 0 0 1 0 Common Stock 2020-10-14 4 C 0 1070172 A 1070172 I See footnotes Common Stock 2020-10-14 4 C 0 828109 A 1898281 I See footnotes Common Stock 2020-10-14 4 P 0 250000 15.00 A 2148281 I See footnote Series A Preferred Stock 2020-10-14 4 C 0 7000000 0.00 D Common Stock 1070172 0 I See footnotes Series B Preferred Stock 2020-10-14 4 C 0 5416666 0.00 D Common Stock 828109 0 I See footnotes Each share of Series A Preferred Stock and Series B Preferred Stock automatically converted into 0.152881822351322 shares of the Issuer's common stock upon the closing of the Issuer's initial public offering on October 14, 2020 (on an adjusted basis, after giving effect to the 1-for-6.541 reverse stock split of the common stock effected by the Issuer on October 2, 2020). The shares have no expiration date. Consists of (i) shares held of record by RiverVest Venture Fund III, L.P. ("RiverVest III"), and (ii) RiverVest Venture Fund III (Ohio), L.P. ("RiverVest (Ohio) III"). The shares held by RiverVest III are indirectly held by RiverVest Venture Partners III, L.P. ("RiverVest Partners III"), which is the general partner of RiverVest III. The shares held by RiverVest (Ohio) III are indirectly held by RiverVest Venture Partners III (Ohio), LLC ("RiverVest Partners (Ohio) III"), which is the general partner of RiverVest (Ohio) III. RiverVest Partners III is the sole member of RiverVest Partners (Ohio) III. RiverVest Venture Partners III, LLC is the general partner of RiverVest Partners III. The individual managers of RiverVest Ventures Partners III, LLC are Thomas C. Melzer, Jay Schmelter and John P. McKearn, Ph.D. RiverVest Partners III, RiverVest Partners (Ohio) III, RiverVest Venture Partners III, LLC and each of the individual managers share voting and dispositive power with regard to the Issuer's securities directly held by RiverVest Venture Fund III, L.P. and RiverVest Venture Fund III (Ohio), L.P. Consists of (i) shares held of record by RiverVest III, (ii) RiverVest (Ohio) III, and (iii) RiverVest Venture Fund IV, L.P. ("RiverVest IV"). The shares held by RiverVest IV are indirectly held by RiverVest Venture Partners IV, L.P., its general partner ("RiverVest Partners IV"). RiverVest Venture Partners IV, LLC is the general partner of RiverVest Partners IV. The individual managers of RiverVest Ventures Partners IV, LLC are Jay Schmelter, John P. McKearn, Ph.D. and Niall O'Donnell, a member of the Issuer's board of directors. RiverVest Partners IV, RiverVest Venture Partners IV, LLC and each of the individual managers share voting and dispositive power with regard to the Company's securities directly held by RiverVest IV. RiverVest IV purchased the shares in the Issuer's initial public offering. The 2,148,281 shares consists of (i) 1,379,177 shares held of record by RiverVest III, (ii) 73,199 shares held of record by RiverVest (Ohio) III, and (iii) 445,905 shares held of record by RiverVest IV. /s/ Jay Schmelter, Manager of RiverVest Venture Partners III, LLC 2020-10-16 /s/ Jay Schmelter, Manager of RiverVest Venture Partners IV, LLC 2020-10-16