IP Library Granted Patent US 12,150,921
Granted Patent B2
US 12,150,921 · App. 18/334,690 · Granted Nov 26, 2024

Epinephrine spray formulations

Inventors: Steven Hartman (Beverly Hills, CA); Michelle Lobel (Beverly Hills, CA); Matthew P. Robben (Pittsford, NY); Kenneth L. Dretchen (Gaithersburg, MD); Michael Mesa (Boyds, MD)
Assignee: Bryn Pharma, LLC
A61K31/137A61K9/0043A61K9/0078A61K9/08A61K9/12A61K47/02A61K47/10A61K47/12A61K47/20A61K47/38A61M11/007A61P37/08A61M15/08A61M2205/3553
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Quick Facts
Patent No.
US 12,150,921
App. No.
18/334,690
Granted
Nov 26, 2024
Kind
B2
Abstract

Provided herein are epinephrine spray formulations. Also provided herein are methods of treating anaphylaxis by administering epinephrine spray formulations to subjects in need of such treatment.

Claims (54)

1. A pharmaceutical nasal spray formulation, comprising:

(a) from about 1% to about 10% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water;

(b) chlorobutanol or chlorobutanol hemihydrate;

(c) sodium bisulfite or sodium metabisulfite;

(d) hypromellose;

(e) citric acid or citric acid monohydrate;

(f) sodium chloride; and

(g) diethylene glycol monoethyl ether,

wherein the pharmaceutical nasal spray formulation has a weight ratio of epinephrine to chlorobutanol or chlorobutanol hemihydrate of about 12:1 to about 30:1.

2. The pharmaceutical nasal spray formulation of claim 1 , comprising chlorobutanol hemihydrate.

3. The pharmaceutical nasal spray formulation of claim 1 , comprising from about 0.01% to about 0.1% (w/w) of sodium bisulfite or sodium metabisulfite.

4. The pharmaceutical nasal spray formulation of claim 1 , comprising from about 0.01% to about 0.2% (w/w) of hypromellose.

5. The pharmaceutical nasal spray formulation of claim 1 , comprising from about 0.1% to about 1% (w/w) of citric acid or citric acid monohydrate.

6. The pharmaceutical nasal spray formulation of claim 1 , comprising from about 0.1% to about 1% (w/w) of sodium chloride.

7. The pharmaceutical nasal spray formulation of claim 1 , comprising from about 0.1% to about 5% (w/w) of diethylene glycol monoethyl ether.

8. The pharmaceutical nasal spray formulation of claim 1 , comprising from about 4% to about 10% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

9. The pharmaceutical nasal spray formulation of claim 1 , comprising about 2% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

10. The pharmaceutical nasal spray formulation of claim 1 , comprising about 6.5% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

11. The pharmaceutical nasal spray formulation of claim 1 , comprising about 6% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

12. The pharmaceutical nasal spray formulation of claim 1 , wherein a pH of the pharmaceutical nasal spray formulation is from about 4.0 to about 6.5.

13. A pharmaceutical nasal spray formulation, comprising:

(a) from about 1% to about 10% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water;

(b) from about 0.1 to about 1.0% (w/w) of chlorobutanol or chlorobutanol hemihydrate;

(c) sodium bisulfite or sodium metabisulfite;

(d) hypromellose;

(e) citric acid or citric acid monohydrate;

(f) sodium chloride; and

(g) diethylene glycol monoethyl ether,

wherein the pharmaceutical nasal spray formulation has a weight ratio of epinephrine to chlorobutanol or chlorobutanol hemihydrate of about 12:1 to about 30:1.

14. The pharmaceutical nasal spray formulation of claim 13 , comprising from about 0.1 to about 1.0% (w/w) of chlorobutanol hemihydrate.

15. The pharmaceutical nasal spray formulation of claim 13 , comprising from about 0.01% to about 0.1% (w/w) of sodium bisulfite or sodium metabisulfite.

16. The pharmaceutical nasal spray formulation of claim 13 , comprising from about 0.01% to about 0.2% (w/w) of hypromellose.

17. The pharmaceutical nasal spray formulation of claim 13 , comprising from about 0.1% to about 1% (w/w) of citric acid or citric acid monohydrate.

18. The pharmaceutical nasal spray formulation of claim 13 , comprising from about 0.1% to about 1% (w/w) of sodium chloride.

19. The pharmaceutical nasal spray formulation of claim 13 , comprising from about 0.1% to about 5% (w/w) of diethylene glycol monoethyl ether.

20. The pharmaceutical nasal spray formulation of claim 13 , comprising from about 4% to about 10% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

21. The pharmaceutical nasal spray formulation of claim 13 , comprising about 2% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

22. The pharmaceutical nasal spray formulation of claim 13 , comprising about 6.5% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

23. The pharmaceutical nasal spray formulation of claim 13 , comprising about 6% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

24. The pharmaceutical nasal spray formulation of claim 13 , wherein the pH of the formulation is from about 4.0 to about 6.5.

25. A pharmaceutical nasal spray formulation, comprising:

(a) from about 1% to about 10% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water;

(b) from about 0.1 to about 1.0% (w/w) of chlorobutanol or chlorobutanol hemihydrate;

(c) from about 0.01% to about 0.1% (w/w) of sodium bisulfite or sodium metabisulfite;

(d) from about 0.01% to about 0.2% (w/w) of hypromellose;

(e) from about 0.1% to about 1% (w/w) of citric acid or citric acid monohydrate;

(f) from about 0.1% to about 1% (w/w) of sodium chloride; and

(g) from about 0.1% to about 5% (w/w) of diethylene glycol monoethyl ether,

wherein the pharmaceutical nasal spray formulation has a weight ratio of epinephrine to chlorobutanol or chlorobutanol hemihydrate of about 12:1 to about 30:1.

26. The pharmaceutical nasal spray formulation of claim 25 , comprising from about 4% to about 10% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

27. The pharmaceutical nasal spray formulation of claim 25 , comprising about 2% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

28. The pharmaceutical nasal spray formulation of claim 25 , comprising about 6.5% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

29. The pharmaceutical nasal spray formulation of claim 25 , comprising about 6% (w/w) of epinephrine, or a pharmaceutically acceptable salt thereof, in water.

30. The pharmaceutical nasal spray formulation of claim 25 , wherein the pH of the formulation is from about 4.0 to about 6.5.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 14, 2023
From: HARTMAN, STEVEN; LOBEL, MICHELLE; ROBBEN, MATTHEW P; DRETCHEN, KENNETH L; MESA, MICHAEL
To: BRYN PHARMA, LLC
Reel/Frame 063949/0139 →
Continuity (9)
Continuation 16930408 · Jul 16, 2020
Continuation 16864183 · May 1, 2020
Continuation 16355525 · Mar 15, 2019
Provisional Application 62810261 · Feb 25, 2019
Provisional Application 62747048 · Oct 17, 2018
Provisional Application 62712678 · Jul 31, 2018
Provisional Application 62663100 · Apr 26, 2018
Provisional Application 62644834 · Mar 19, 2018
Related Publication 20230364036A1 · Nov 16, 2023
Cited By (8)
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