IP Library Granted Patent US 11,311,486
Granted Patent B1
US 11,311,486 · App. 17/536,478 · Granted Apr 26, 2022

Manufacturing of bupivacaine multivesicular liposomes

Inventors: Jeffrey S. Hall (San Diego, CA); David J. Turnbull (San Diego, CA); John J. Grigsby, Jr. (San Diego, CA); Soroush M. Ardekani (San Diego, CA); Paige N. Davis (San Diego, CA); Louie D. Garcia (San Diego, CA); Stephanie M. Kurz (San Diego, CA); Kathleen D. A. Los (San Diego, CA)
Assignee: Pacira Pharmaceuticals, Inc.
A61K9/1277A61K31/451B01D61/142B01D61/147B01F23/4105B01F23/808B01D2315/10B01D2315/16B01F23/4144B01F23/4145B01F2101/22B01F2215/044B01F2215/0477B01F2215/0481
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Quick Facts
Patent No.
US 11,311,486
App. No.
17/536,478
Granted
Apr 26, 2022
Kind
B1
Abstract

Embodiments of the present application relate to commercial manufacturing processes for making bupivacaine multivesicular liposomes (MVLs) using independently operating dual tangential flow filtration modules.

Claims (37)

1. A composition of bupivacaine encapsulated multivesicular liposomes (MVLs), comprising:

bupivacaine encapsulated MVLs comprising bupivacaine residing inside a plurality of internal aqueous chambers of MVLs separated by lipid membranes, wherein the lipid membranes comprise 1,2-dierucoylphosphatidylcholine (DEPC), 1,2-dipalmitoyl-sn-glycero-3 phospho-rac-(1-glycerol) (DPPG), cholesterol, and at least one neutral lipid, the plurality of internal aqueous chambers of the MVLs also comprise lysine; and

an aqueous medium in which the bupivacaine encapsulated MVLs are suspended, wherein the aqueous medium also comprises unencapsulated bupivacaine;

wherein the bupivacaine concentration in the composition is from about 11.3 mg/mL to about 17.0 mg/mL, wherein an erucic acid concentration in the composition is about 53 μg/mL or less after the composition is stored at 25° C. for three months.

2. The composition of claim 1 , wherein the composition has a pH of about 6.9 after the composition is stored at 25° C. for three months.

3. The composition of claim 1 , wherein the erucic acid concentration in the composition is about 99 μg/mL or less after the composition is stored at 25° C. for six months.

4. The composition of claim 3 , wherein the composition has a pH of about 6.5 after the composition is stored at 25° C. for six months.

5. The composition of claim 3 , wherein the at least one neutral lipid in the lipid membranes comprises tricaprylin.

6. The composition of claim 3 , wherein the encapsulated lysine concentration in the bupivacaine encapsulated MVLs composition is about 0.03 μg/mL.

7. The composition of claim 3 , wherein the bupivacaine concentration in the composition is about 13.3 mg/mL.

8. The composition of claim 3 , wherein the DEPC and DPPG in the composition is in a mass ratio of about 7:1 to about 10:1.

9. The composition of claim 3 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated MVLs in the composition is about 32% to 44%.

10. The composition of claim 3 , wherein the bupivacaine is in a salt form.

11. The composition of claim 10 , wherein the bupivacaine is in the form of bupivacaine phosphate.

12. The composition of claim 1 , wherein the aqueous medium comprises a saline solution.

13. The composition of claim 3 , wherein the aqueous medium comprises a saline solution.

14. A method of treating or ameliorating pain in a subject in need thereof, comprising administering the composition of claim 3 to the subject.

15. The method of claim 14 , wherein the administration is via local infiltration to a surgical site to provide postsurgical local analgesia.

16. The method of claim 14 , wherein the administration is via interscalene brachial plexus nerve block or femoral nerve block to provide postsurgical regional analgesia.

17. The method of claim 14 , wherein the composition has a volume of 10 mL or 20 mL for a single-dose administration.

18. The method of claim 14 , wherein the composition has a pH of about 6.5 after the composition is stored at 25° C. for six months.

19. The method of claim 14 , wherein the at least one neutral lipid in the lipid membranes comprises tricaprylin.

20. The method of claim 14 , wherein the encapsulated lysine concentration in the bupivacaine encapsulated MVLs composition is about 0.03 μg/mL.

21. The method of claim 14 , wherein the bupivacaine concentration in the composition is about 13.3 mg/mL.

22. The method of claim 14 , wherein the DEPC and DPPG in the composition is in a mass ratio of about 7:1 to about 10:1.

23. The method of claim 14 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated MVLs in the composition is about 32% to 44%.

24. The method of claim 14 , wherein the bupivacaine is in a salt form.

25. The method of claim 24 , wherein the bupivacaine is in the form of bupivacaine phosphate.

26. The method of claim 14 , wherein the aqueous medium comprises a saline solution.

27. The method of claim 21 , wherein the encapsulated lysine concentration in the bupivacaine encapsulated MVLs composition is about 0.03 μg/mL.

28. The method of claim 21 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated MVLs in the composition is about 32% to 44%.

29. The method of claim 28 , wherein the bupivacaine is in a salt form.

30. The method of claim 29 , wherein the bupivacaine is in the form of bupivacaine phosphate.

31. The method of claim 30 , wherein the aqueous medium comprises a saline solution.

32. The method of claim 21 , wherein the administration is via local infiltration to a surgical site to provide postsurgical local analgesia.

33. The method of claim 21 , wherein the administration is via interscalene brachial plexus nerve block or femoral nerve block to provide postsurgical regional analgesia.

34. The method of claim 21 , wherein the composition has a volume of 10 mL or 20 mL for a single-dose administration.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Dec 5, 2025
From: JPMORGAN CHASE BANK, N.A.
To: PACIRA CRYOTECH, INC.; PACIRA PHARMACEUTICALS, INC.; PACIRA THERAPEUTICS, INC. (F/K/A FLEXION THERAPEUTICS, INC.)
Reel/Frame 073779/0532 →
SECURITY INTEREST Recorded Jul 4, 2025
From: PACIRA PHARMACEUTICALS, INC.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 071814/0792 →
CONFIRMATORY GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Mar 31, 2023
From: PACIRA CRYOTECH, INC.; PACIRA PHARMACEUTICALS, INC.; PACIRA THERAPEUTICS, INC. (F/K/A FLEXION THERAPEUTICS, INC.)
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063214/0108 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 8, 2022
From: HALL, JEFFREY S.; TURNBULL, DAVID J.; GRIGSBY, JOHN J., JR.; ARDEKANI, SOROUSH M.; DAVIS, PAIGE N.; GARCIA, LOUIE D.; KURZ, STEPHANIE M.; LOS, KATHLEEN D.A.
To: PACIRA PHARMACEUTICALS, INC.
Reel/Frame 058931/0986 →
Cited By (1)
US 12,514,756