IP Library Granted Patent US 11,357,727
Granted Patent B1
US 11,357,727 · App. 17/156,385 · Granted Jun 14, 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.
A61K9/1277A61K9/0085A61K31/445A61K47/183A61K47/26
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Quick Facts
Patent No.
US 11,357,727
App. No.
17/156,385
Granted
Jun 14, 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 (40)

1. A composition of bupivacaine encapsulated multivesicular liposomes (MVLs) prepared by a process, the process comprising:

(a) mixing a first aqueous solution comprising phosphoric acid with a volatile water-immiscible solvent solution to form a water-in-oil first emulsion, wherein the volatile water-immiscible solvent solution comprises bupivacaine, 1, 2-dierucoylphosphatidylcholine (DEPC), 1, 2-dipalmitoyl-sn-glycero-3 phospho-rac-(1-glycerol) (DPPG), and at least one neutral lipid;

(b) mixing the water-in-oil first emulsion with a second aqueous solution to form a water-in-oil-in-water second emulsion, wherein the second aqueous solution comprises lysine and dextrose;

(c) removing the volatile water-immiscible solvent from the water-in-oil-in-water second emulsion to form a first aqueous suspension of bupivacaine encapsulated MVLs having a first volume;

(d) reducing the first volume of the first aqueous suspension of bupivacaine encapsulated MVLs by microfiltration to provide a second aqueous suspension of bupivacaine encapsulated MVLs having a second volume;

(e) exchanging the aqueous supernatant of the second aqueous suspension with a saline solution by diafiltration to provide a third aqueous suspension of bupivacaine encapsulated MVLs having a third volume; and

(f) further reducing the volume of the third aqueous suspension by microfiltration to provide a final aqueous suspension of bupivacaine encapsulated MVLs having a target concentration of bupivacaine;

wherein all steps in the process are carried out under aseptic conditions; and

wherein the internal pH of the bupivacaine encapsulated MVLs in the composition is about 5.50.

2. The composition of claim 1 , wherein the encapsulated lysine concentration of the bupivacaine encapsulated MVLs composition is about 0.030 μg/mL to about 0.032 μg/mL.

3. The composition of claim 2 , wherein the encapsulated lysine concentration of the bupivacaine encapsulated MVLs composition is about 0.031 μg/mL.

4. The composition of claim 1 , wherein the encapsulated dextrose concentration of the bupivacaine encapsulated MVLs composition is about 1.25 μg/mL to about 1.32 μg/mL.

5. The composition of claim 4 , wherein the encapsulated dextrose concentration of the bupivacaine encapsulated MVLs composition is about 1.29 μg/mL.

6. The composition of claim 1 , wherein the mixing of step (a) is performed using a first mixer at a high shear speed.

7. The composition of claim 6 , wherein the high sheer speed is from about 1100 rpm to about 1200 rpm.

8. The composition of claim 7 , wherein the high sheer speed is about 1150 rpm.

9. The composition of claim 8 , wherein the mixing of step (a) is performed for about 65 to 75 minutes.

10. The composition of claim 1 , wherein the mixing of step (b) is performed using a second mixer at a low shear speed.

11. The composition of claim 10 , wherein the low shear speed is from about 450 rpm to about 510 rpm.

12. The composition of claim 11 , wherein the low shear speed is about 495 rpm.

13. The composition of claim 12 , wherein the mixing of step (b) is performed for about 60 to 65 seconds.

14. The composition of claim 1 , wherein the target concentration of bupivacaine in the final aqueous suspension is from about 11.3 mg/mL to about 17.0 mg/mL.

15. The composition of claim 1 , wherein the concentration of bupivacaine in the composition is about 13.3 mg/mL.

16. The composition of claim 1 , wherein the d 50 of the multivesicular liposomes in the composition is about 24 μm to about 31 μm, or about 27 μm.

17. The composition of claim 1 , wherein the final aqueous suspension of bupivacaine encapsulated MVLs has a volume of about 200 L to about 225 L.

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

19. The method of claim 18 , wherein the administration is via local infiltration to a surgical site to provide local analgesia.

20. The method of claim 18 , wherein the administration is via interscalene brachial plexus nerve block or femoral nerve block to provide regional analgesia.

21. The method of claim 18 , wherein the concentration of bupivacaine in the composition is about 13.3 mg/mL.

22. The composition of claim 1 , wherein the composition has a pH of about 7.0 to about 7.4.

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

24. 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%.

25. The method of claim 18 , wherein encapsulated lysine concentration of the bupivacaine encapsulated MVLs composition is about 0.030 μg/mL to about 0.032 μg/mL.

26. The method of claim 25 , wherein the encapsulated lysine concentration of the bupivacaine encapsulated MVLs composition is about 0.031 μg/mL.

27. The method of claim 18 , wherein encapsulated dextrose concentration of the bupivacaine encapsulated MVLs composition is about 1.25 μg/mL to about 1.32 μg/mL.

28. The method of claim 27 , wherein the encapsulated dextrose concentration of the bupivacaine encapsulated MVLs composition is about 1.29 μg/mL.

29. The method of claim 18 , wherein the lipid membranes further comprise cholesterol and tricaprylin.

30. The method of claim 18 , wherein the composition has a pH of about 7.0 to about 7.4.

31. The method of claim 18 , wherein the d 50 of the multivesicular liposomes in the composition is about 24 μm to about 31 μm, or about 27 μm.

32. The method of claim 18 , wherein the percent packed particle volume (% PPV) of the bupivacaine encapsulated multivesicular liposomes in the composition is about 35% to 40%.

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 Sep 20, 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 057535/0498 →
Cited By (1)
US 12,514,756