IP Library Granted Patent US 11,278,494
Granted Patent B1
US 11,278,494 · App. 17/156,424 · Granted Mar 22, 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.
A61K9/127A61K31/445A61K47/12A61K47/14A61K47/183A61K47/28
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Quick Facts
Patent No.
US 11,278,494
App. No.
17/156,424
Granted
Mar 22, 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 (63)

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

bupivacaine residing inside a plurality of internal aqueous chambers of the 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), and at least one neutral lipid; and

an aqueous medium in which the bupivacaine encapsulated MVLs are suspended;

wherein erucic acid concentration in the composition is about 23 μg/mL or less after the composition is stored at 25° C. for one month.

2. The composition of claim 1 , wherein the composition has an initial pH of about 7.4.

3. The composition of claim 2 , wherein the composition has a pH of about 7.1 after the composition is stored at 25° C. for one month.

4. The composition of claim 1 , wherein the erucic acid concentration in the composition is about 38 μg/mL or less after the composition is stored at 25° C. for two months.

5. The composition of claim 4 , wherein the composition has a pH of about 7.1 after the composition is stored at 25° C. for two months.

6. The composition of claim 1 , wherein the erucic acid concentration in the composition is about 54 μg/mL or less after the composition is stored at 25° C. for three months.

7. The composition of claim 6 , wherein the composition has a pH of about 6.9 after the composition is stored at 25° C. for three months.

8. 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.

9. The composition of claim 8 , wherein the composition has a pH of about 6.5 after the composition is stored at 25° C. for six months.

10. The composition of claim 1 , wherein the lipid membranes further comprise cholesterol and tricaprylin.

11. The composition of claim 1 , wherein the plurality of internal aqueous chambers of the MVLs comprise lysine.

12. The composition of claim 1 , wherein the plurality of internal aqueous chambers of the MVLs has an initial pH of about 5.50.

13. The composition of claim 1 , wherein the bupivacaine concentration in the composition is from about 11.3 mg/mL to about 17.0 mg/mL.

14. The composition of claim 13 , wherein the bupivacaine concentration in the composition is about 13.3 mg/mL.

15. The composition of claim 1 , wherein the composition comprises less than 5% by weight unencapsulated bupivacaine.

16. The composition of claim 1 , wherein the d 50 of the multivesicular liposomes in the composition is about 27 μm.

17. The composition of claim 1 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated multivesicular liposomes in the composition is about 35% to 40%.

18. The composition of claim 1 , prepared by a commercial process having a final product volume of about 200 L to about 225 L.

19. A method of treating or ameliorating post surgical pain in a subject in need thereof, comprising administering a composition of claim 1 to the subject.

20. The method of claim 19 , wherein the administration is via local infiltration to a surgical site to provide local analgesia.

21. The method of claim 19 , wherein the administration is via interscalene brachial plexus nerve block or femoral nerve block to provide regional analgesia.

22. The composition of claim 8 , wherein the composition has an initial pH of about 7.4.

23. The composition of claim 8 , wherein the lipid membranes further comprise cholesterol and tricaprylin.

24. The composition of claim 8 , wherein the plurality of internal aqueous chambers of the MVLs comprise lysine.

25. The composition of claim 8 , wherein the plurality of internal aqueous chambers of the MVLs has an initial pH of about 5.50.

26. The composition of claim 8 , wherein the bupivacaine concentration in the composition is from about 11.3 mg/mL to about 17.0 mg/mL.

27. The composition of claim 26 , wherein the bupivacaine concentration in the composition is about 13.3 mg/mL.

28. The composition of claim 8 , wherein the composition comprises less than 5% by weight unencapsulated bupivacaine.

29. The composition of claim 8 , wherein the d 50 of the multivesicular liposomes in the composition is about 27 μm.

30. The composition of claim 8 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated multivesicular liposomes in the composition is about 35% to 40%.

31. The composition of claim 8 , prepared by a commercial process having a final product volume of about 200 L to about 225 L.

32. The method of claim 19 , wherein the composition has an initial pH of about 7.4.

33. The method of claim 19 , wherein the composition has a pH of about 7.1 after the composition is stored at 25° C. for one month.

34. The method of claim 19 , wherein the erucic acid concentration in the composition is about 38 μg/mL or less after the composition is stored at 25° C. for two months.

35. The method of claim 34 , wherein the composition has a pH of about 7.1 after the composition is stored at 25° C. for two months.

36. The method of claim 19 , wherein the erucic acid concentration in the composition is about 54 μg/mL or less after the composition is stored at 25° C. for three months.

37. The method of claim 36 , wherein the composition has a pH of about 6.9 after the composition is stored at 25° C. for three months.

38. The method of claim 19 , 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.

39. The method of claim 38 , wherein the composition has a pH of about 6.5 after the composition is stored at 25° C. for six months.

40. The method of claim 19 , wherein the lipid membranes further comprise cholesterol and tricaprylin.

41. The method of claim 19 , wherein the plurality of internal aqueous chambers of the MVLs comprise lysine.

42. The method of claim 19 , wherein the plurality of internal aqueous chambers of the MVLs has an initial pH of about 5.50.

43. The method of claim 19 , wherein the bupivacaine concentration in the composition is from about 11.3 mg/mL to about 17.0 mg/mL.

44. The method of claim 43 , wherein the bupivacaine concentration in the composition is about 13.3 mg/mL.

45. The method of claim 19 , wherein the composition comprises less than 5% by weight unencapsulated bupivacaine.

46. The method of claim 19 , wherein the d 50 of the multivesicular liposomes in the composition is about 27 μm.

47. The method of claim 19 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated multivesicular liposomes in the composition is about 35% to 40%.

48. The method of claim 19 , wherein the composition is prepared by a commercial process having a final product volume of about 200 L to about 225 L.

49. The method of claim 38 , wherein the composition has an initial pH of about 7.4.

50. The method of claim 38 , wherein the lipid membranes further comprise cholesterol and tricaprylin.

51. The method of claim 38 , wherein the plurality of internal aqueous chambers of the MVLs comprise lysine.

52. The method of claim 38 , wherein the plurality of internal aqueous chambers of the MVLs has an initial pH of about 5.50.

53. The method of claim 38 , wherein the bupivacaine concentration in the composition is from about 11.3 mg/mL to about 17.0 mg/mL.

54. The method of claim 53 , wherein the bupivacaine concentration in the composition is about 13.3 mg/mL.

55. The method of claim 38 , wherein the composition comprises less than 5% by weight unencapsulated bupivacaine.

56. The method of claim 38 , wherein the d 50 of the multivesicular liposomes in the composition is about 27 μm.

57. The method of claim 38 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated multivesicular liposomes in the composition is about 35% to 40%.

58. The method of claim 38 , wherein the composition is prepared by a commercial process having a final product volume of about 200 L to about 225 L.

59. The method of claim 38 , wherein the administration is via local infiltration to a surgical site to provide local analgesia.

60. The method of claim 38 , wherein the administration is via interscalene brachial plexus nerve block or femoral nerve block to provide regional analgesia.

Assignments (6)
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: JPMORGAN CHASE BANK, N.A.
To: PACIRA CRYOTECH, INC.; PACIRA PHARMACEUTICALS, INC.; PACIRA THERAPEUTICS, INC. (F/K/A FLEXION THERAPEUTICS, INC.)
Reel/Frame 063213/0864 →
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 →
SUPPLEMENTAL CONFIRMATORY GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Dec 14, 2021
From: PACIRA CRYOTECH, INC.; PACIRA PHARMACEUTICALS, INC.; FLEXION THERAPEUTICS, INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 058516/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2021
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 057695/0298 →
Cited By (10)
US 12,226,610 US 12,246,092 US 12,251,468 US 12,251,472 US 12,280,149 US 12,285,419 US 12,296,047 US 12,318,483 US 12,370,142 US 12,514,756