Glycopyrrolate salts
View Patent ↗Salts of glycopyrrolate, including solid forms and formulations such as topicals thereof, are disclosed. Methods of making glycopyrrolate salts, including formulations such as topicals thereof, and methods of treating hyperhidrosis with salts of glycopyrrolate, and formulations such as topicals thereof, are disclosed.
1. A pharmaceutically acceptable solution comprising a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate or a solvate thereof, and at least one pharmaceutically acceptable additive, wherein the pH of said pharmaceutically acceptable solution is between 3.5 and 5.5.
2. The pharmaceutically acceptable solution of claim 1 , wherein the pH of said pharmaceutically acceptable solution is between about 4.0 and 5.0, between about 4.0 and 4.7, or between about 4.1 and 4.6.
3. The pharmaceutically acceptable solution of claim 2 , wherein said pharmaceutically acceptable solution is clear and colorless or pale yellow at a pH of between about 4.0 and about 5.0 at 25° C.
4. The pharmaceutically acceptable solution of claim 3 , wherein said additive is citric acid, sodium citrate, or a combination thereof as a buffer.
5. The pharmaceutically acceptable solution of claim 4 , further comprising ethanol.
6. The pharmaceutically acceptable solution of claim 5 , further comprising at least one pharmaceutically acceptable excipient.
7. The pharmaceutically acceptable solution of claim 6 , further comprising povidone as a binding agent and a butyl ester of a polyvinylmethylether/maleic anhydride acid copolymer as a film-forming agent.
8. The pharmaceutically acceptable solution of claim 1 , wherein said pH is between about 4.0 and about 5.0 at 25° C. and further comprises ethanol and a buffer comprising citric acid, sodium citrate, or a combination thereof.
9. The pharmaceutically acceptable solution of claim 8 , further comprising povidone as a binding agent and a butyl ester of a polyvinylmethylether/maleic anhydride acid copolymer as a film-forming agent.
10. A topical composition comprising a glycopyrrolate tosylate comprising a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate or a solvate thereof, and at least one pharmaceutically acceptable additive, wherein the pH of said topical is between 3.5 and 5.5.
11. The topical composition of claim 10 , wherein the weight percent of said glycopyrrolate tosylate, is between about 1% and about 4%, between about 1.25% and about 4%, or between about 2.5% and about 3.75%.
12. The topical composition of claim 11 , wherein said weight percent of said glycopyrrolate tosylate is about 1.25%, about 2.5%, or about 3.75%.
13. The topical composition of claim 11 , wherein said topical composition is an ointment, a gel, a lotion, a spray, a cream, a paste, or a wash.
14. The topical composition of claim 11 , wherein said topical composition is an a patch, a dressing, a mask, a gauze, a bandage, a swab, or a pad.
15. The topical composition of claim 13 , wherein said topical composition further comprises citric acid, sodium citrate, or a combination thereof as a buffer.
16. The topical composition of claim 10 , wherein said topical composition further comprises ethanol.
17. The topical composition of claim 10 , further comprising povidone as a binding agent.
18. The topical composition of claim 10 , further comprising a butyl ester of a polyvinylmethylether/maleic anhydride acid copolymer as a film-forming agent.
19. An absorbent pad containing an aqueous glycopyrrolate solution comprising a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate or a solvate thereof, about 0.15% by weight anhydrous citric acid, about 0.06% sodium citrate dihydrate by weight, and between about 57 to about 59.5% by weight of dehydrated ethanol, wherein said glycopyrrolate solution comprises between about 1% and about 6% by weight glycopyrrolate tosylate and the pH said aqueous glycopyrrolate solution is between 3.5 and 5.5.
20. The absorbent pad of claim 19 , wherein the pH of said aqueous glycopyrrolate solution is between about 4.0 and 5.0, between about 4.0 and 4.7, or between about 4.1 and 4.6.
21. The absorbent pad of claim 19 , wherein said pad comprises polypropylene.
22. The absorbent pad of claim 21 , wherein said pad is substantially polypropylene.
23. The absorbent pad of claim 22 , wherein said pad is 100% polypropylene.
24. The absorbent pad of claim 19 , wherein said pH is between about 4.0 and about 5.0 at 25° C. and said aqueous glycopyrrolate solution further comprises a buffer comprising citric acid, sodium citrate, or a combination thereof.