IP Library Granted Patent US 11,033,495
Granted Patent B1
US 11,033,495 · App. 17/156,400 · Granted Jun 15, 2021

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.
A61K9/1277A61K31/451B01D61/142B01D61/147B01F3/0811B01F3/2261B01D2315/10B01D2315/16B01F2003/0838B01F2003/0842B01F2215/0032B01F2215/044B01F2215/0477B01F2215/0481
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Quick Facts
Patent No.
US 11,033,495
App. No.
17/156,400
Granted
Jun 15, 2021
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 (30)

1. A composition of bupivacaine encapsulated multivesicular liposomes (MVLs) prepared by a commercial scale process, the commercial scale 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 third volume of the third aqueous suspension by microfiltration to provide a final aqueous suspension of bupivacaine encapsulated MVLs having a target concentration from about 12.6 mg/mL to about 17.0 mg/mL;

wherein all steps are carried out under aseptic conditions; and

wherein the 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 a pH of about 7.1 after the composition is stored at 25° C. for one month.

3. 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.

4. The composition of claim 3 , wherein the composition has a pH of about 7.1 after the composition is stored at 25° C. for two months.

5. 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 month.

6. The composition of claim 5 , wherein the composition has a pH of about 6.9 after the composition is stored at 25° C. for three months.

7. 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.

8. The composition of claim 7 , wherein the composition has a pH of about 6.5 after the composition is stored at 25° C. for six months.

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

10. The composition of claim 9 , wherein the high sheer speed is from about 1100 rpm to about 1200 rpm.

11. The composition of claim 10 , wherein the high sheer speed is about 1150 rpm.

12. The composition of claim 11 , wherein the mixing time in step (a) is about 65 to 75 minutes.

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

14. The composition of claim 13 , wherein the low shear speed is from about 450 rpm to about 510 rpm.

15. The composition of claim 14 , wherein the low shear speed is about 495 rpm.

16. The composition of claim 15 , wherein the mixing time in step (b) is about 60 to 65 seconds.

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

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

19. The composition of claim 1 , wherein the internal pH of the bupivacaine encapsulated MVLs in the composition is about 5.5.

20. A method of providing post surgical pain management in a subject in need thereof, comprising administering a composition of claim 1 to the subject.

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

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

Assignments (5)
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 May 7, 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 056172/0899 →
Cited By (11)
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 12,433,878 US 12,514,756