X0306 4 2021-03-17 0 0001087294 CUMBERLAND PHARMACEUTICALS INC CPIX 0001408500 Cearnal Martin E 2525 WEST END AVE. SUITE 950 NASHVILLE TN 37203 1 1 0 0 Sr VP/Chief Commercial Officer Common Stock 2021-03-17 4 F 0 2945 3.22 D 148814 D Common Stock 2021-04-16 4 P 0 105 3.03 A 148919 D Common Stock 2021-04-19 4 P 0 105 3.04 A 149024 D Common Stock 2021-04-20 4 P 0 105 3.02 A 149129 D Common Stock 2021-04-21 4 P 0 105 2.97 A 149234 D Common Stock 2021-04-22 4 P 0 105 2.96 A 149339 D Common Stock 2021-04-23 4 P 0 105 2.99 A 149444 D Common Stock 2021-04-26 4 P 0 105 2.97 A 149549 D Common Stock 2021-04-27 4 P 0 105 2.94 A 149654 D Common Stock 2021-04-28 4 P 0 80 2.94 A 149734 D Common Stock 2021-04-29 4 P 0 105 2.89 A 149839 D Common Stock 2021-04-30 4 P 0 105 2.78 A 149944 D Common Stock 2021-05-03 4 P 0 105 2.66 A 150049 D Common Stock 2021-05-04 4 P 0 105 2.66 A 150154 D Common Stock 2021-05-05 4 P 0 105 2.73 A 150259 D Common Stock 2021-05-06 4 P 0 105 2.74 A 150364 D Common Stock 2021-05-07 4 P 0 105 2.73 A 150469 D Common Stock 2021-05-10 4 P 0 105 2.71 A 150574 D Common Stock 2021-05-11 4 P 0 105 2.68 A 150679 D Common Stock 2021-05-12 4 P 0 105 2.86 A 150784 D Common Stock 2021-05-13 4 P 0 105 2.88 A 150889 D Common Stock 2021-05-14 4 P 0 105 2.81 A 150994 D Common Stock 2021-05-14 4 P 0 5000 2.77 A 155994 D Common Stock 2021-05-17 4 P 0 105 2.84 A 156099 D Common Stock 2021-05-17 4 P 0 5700 2.83 A 161799 D Options (right to buy) 3.22 2021-03-17 4 A 0 5000 0.00 A 2025-03-17 2031-03-17 Common Stock 5000 5000 D This transaction represents shares withheld/purchased by the Company to cover the tax withholding obligations for the vesting of shares. The purchases reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person during March 2021. The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions at prices ranging from $2.715 to $2.792, inclusive. The reporting person undertakes to provide to Cumberland Pharmaceuticals Inc., any security holder of Cumberland Pharmaceuticals Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in footnotes (3) and (4) to this Form 4. The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions at prices ranging from $2.805 to $2.8797, inclusive. 100% vesting on March 17, 2025. Martin E. Cearnal by /s/ John Hamm as attorney-in-fact 2021-06-08