IP Library Granted Patent US 10,471,148
Granted Patent B2
US 10,471,148 · App. 15/454,898 · Granted Nov 12, 2019

Progesterone formulations having a desirable PK profile

Inventors: Janice Cacace (St. Petersburg, FL); Peter H. R. Persicaner (Boca Raton, FL); Thorsteinn Thorsteinsson (West Palm Beach, FL); Frederick Sancilio (Palm Beach Gardens, FL); Julia Amadio (Boca Raton, FL); Brian Bernick (Boca Raton, FL)
Assignee: TherapeuticsMD, Inc.
A61K47/14A61K9/4825A61K9/4858A61K31/57
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Quick Facts
Patent No.
US 10,471,148
App. No.
15/454,898
Granted
Nov 12, 2019
Kind
B2
Abstract

This disclosure provides progesterone formulations, methods of using these formulations, and their related pharmacokinetic parameters. In particular embodiments, the formulations disclosed herein allow for a reduction in the amount of progesterone administered to a patient in need thereof, while still providing the benefits of a larger dosage amount.

Claims (44)

1. A pharmaceutical composition for orally administering progesterone to a subject in need thereof, the composition comprising:

progesterone;

a solubilizing agent; and

a nonionic surfactant;

wherein the solubilizing agent comprises predominantly C 6 -C 12 fatty acid tri-esters of glycerol;

wherein the progesterone is present from about 20 to about 50 weight percent of the composition; and

wherein the composition provides increased progesterone bioavailability compared to micronized progesterone suspended in peanut oil.

2. The pharmaceutical composition of claim 1 , wherein the solubilizing agent further comprises a C 6 -C 12 fatty acid mono-ester of glycerol.

3. The pharmaceutical composition of claim 2 , wherein the solubilizing agent further comprises a C 6 -C 12 fatty acid di-ester of glycerol.

4. The pharmaceutical composition of claim 1 , wherein the tri-ester of glycerol comprises predominantly esters of caprylic fatty acid (C 8 ) and capric fatty acid (C 10 ).

5. The pharmaceutical composition of claim 1 , wherein the nonionic surfactant is lauroyl polyoxyl-32 glycerides.

6. The pharmaceutical composition of claim 1 , wherein the nonionic surfactant is lauroyl macrogol-32 EP.

7. The pharmaceutical composition of claim 1 , wherein the nonionic surfactant is caprylocaproyl macrogol-8 glyceride EP.

8. The pharmaceutical composition of claim 1 , wherein the amount of progesterone is from 25 mg to 200 mg.

9. The pharmaceutical composition of claim 1 , wherein the amount of progesterone is 75 mg or 150 mg.

10. The pharmaceutical composition of claim 1 , wherein the progesterone includes solubilized progesterone and suspended progesterone.

11. The pharmaceutical composition of claim 1 , wherein the composition is provided in a gelatin capsule.

12. The pharmaceutical composition of claim 1 , wherein the composition has a total mass of less than 500 mg.

13. The pharmaceutical composition of claim 1 , wherein the composition provides a 25% increase in progesterone bioavailability compared to micronized progesterone suspended in peanut oil.

14. The pharmaceutical composition of claim 1 , wherein the amount of progesterone comprises about 33% by weight of the composition; the solubilizing agent comprises about 65% by weight of the composition, the non-ionic surfactant comprises about 1.7% by weight of the composition.

15. The pharmaceutical composition of claim 1 , wherein the amount of progesterone comprises about 33.33% by weight of the composition; the solubilizing agent comprises about 64.93% by weight of the composition, the non-ionic surfactant comprises about 1.67% by weight of the composition.

16. The pharmaceutical composition of claim 14 , further comprising an antioxidant.

17. The pharmaceutical composition of claim 16 , wherein the antioxidant is butylated hydroxy toluene.

18. The pharmaceutical composition of claim 17 , wherein the solubilizing agent is medium chain triglycerides of caprylic fatty acid (C 8 ) and capric fatty acid (C 10 ).

19. The pharmaceutical composition of claim 18 , wherein the non-ionic surfactant is lauroyl polyoxyl-32 glycerides.

20. The pharmaceutical composition of claim 19 , wherein the amount of progesterone is 200 mg.

21. The pharmaceutical composition of claim 19 , wherein the amount of progesterone is 150 mg.

22. The pharmaceutical composition of claim 19 , wherein the progesterone is ultra-micronized and has an X50 of less than or equal to 15 microns.

23. The pharmaceutical composition of claim 1 , wherein the progesterone is ultra-micronized and has an X90 of less than or equal to 25 microns.

24. The pharmaceutical composition of claim 1 , wherein the progesterone is the sole active ingredient in the composition.

25. A pharmaceutical composition for orally administering progesterone to a subject in need thereof, the composition comprising:

progesterone;

a solubilizing agent; and

a nonionic surfactant;

wherein the solubilizing agent comprises predominantly C 6 -C 12 fatty acid tri-esters of glycerol;

wherein the progesterone is present from about 20 to about 50 weight percent of the composition and wherein less than 6 percent of the progesterone is soluble in the solubilizing agent; and

wherein the composition provides increased progesterone bioavailability compared to micronized progesterone suspended in peanut oil.

26. The pharmaceutical composition of claim 25 , wherein more than 5 percent of the progesterone is soluble in the solubilizing agent.

27. A method of treating a progesterone-deficient state in a subject in need thereof, the method comprising administering to a subject in need thereof an effective amount of the pharmaceutical composition of claim 1 .

28. The method of claim 27 , wherein the progesterone-deficient state is endometrial hyperplasia, secondary amenorrhea, preterm birth, shortened cervix, or another disease states or condition treated with supplemental progesterone.

29. The method of claim 28 , wherein the progesterone-deficient state is secondary amenorrhea.

30. A method of treating a progesterone-deficient state in a subject in need thereof, the method comprising administering to a subject in need thereof an effective amount of the pharmaceutical composition of claim 25 .

31. The method of claim 30 , wherein the progesterone-deficient state is endometrial hyperplasia, secondary amenorrhea, preterm birth, shortened cervix, or another disease states or condition treated with supplemental progesterone.

32. The method of claim 31 , wherein the progesterone-deficient state is secondary amenorrhea.

Assignments (10)
TERMINATION AND RELEASE OF GRANT OF A SECURITY INTEREST - PATENTS Recorded Dec 30, 2022
From: SIXTH STREET SPECIALTY LENDING, INC. (F/K/A TPG SPECIALTY LENDING, INC.)
To: THERAPEUTICSMD, INC.
Reel/Frame 062254/0813 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NO. 16/401,844 PREVIOUSLY RECORDED AT REEL: 050928 FRAME: 0987. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF ADDRESS. Recorded Sep 24, 2021
From: THERAPEUTICSMC, INC.
To: THERAPEUTICSMD, INC.
Reel/Frame 057698/0571 →
SECURITY INTEREST Recorded Jan 27, 2021
From: THERAPEUTICSMD, INC.
To: SIXTH STREET SPECIALTY LENDING, INC. (F/K/A TPG SPECIALTY LENDING, INC.)
Reel/Frame 055049/0651 →
SECURITY INTEREST Recorded Sep 18, 2020
From: THERAPEUTICSMD, INC.
To: SIXTH STREET SPECIALTY LENDING, INC. (F/K/A TPG SPECIALTY LENDING, INC.)
Reel/Frame 053820/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2019
From: IRANI, NEDA
To: THERAPEUTICSMD, INC.
Reel/Frame 050942/0698 →
CHANGE OF ADDRESS Recorded Nov 5, 2019
From: THERAPEUTICSMD, INC.
To: THERAPEUTICSMD, INC.
Reel/Frame 050928/0987 →
RELEASE OF SECURITY INTEREST Recorded Apr 26, 2019
From: MIDCAP FINANCIAL TRUST, AS AGENT
To: THERAPEUTICSMD, INC.; VITAMEDMD, LLC; BOCAGREENMD, INC.; VITACARE PRESCRIPTION SERVICES, INC.
Reel/Frame 049012/0215 →
PATENT SECURITY AGREEMENT Recorded Apr 24, 2019
From: THERAPEUTICSMD, INC.
To: TPG SPECIALTY LENDING, INC.
Reel/Frame 048990/0820 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2018
From: AMADIO, JULIA; BERNICK, BRIAN; PERSICANER, PETER; CACACE, JANICE; THORSTEINNSON, THORSTEINN; SANCILLIO, FREDERICK
To: THERAPEUTICSMD, INC.
Reel/Frame 046294/0612 →
SECURITY INTEREST Recorded May 2, 2018
From: THERAPEUTICSMD, INC.; VITAMEDMD, LLC; BOCAGREENMD, INC.; VITACARE PRESCRIPTION SERVICES, INC.
To: MIDCAP FINANCIAL TRUST, AS AGENT
Reel/Frame 046053/0723 →
Cited By (2)
US 12,208,103 US 12,527,805