IP Library Granted Patent US 11,179,336
Granted Patent B1
US 11,179,336 · App. 17/319,956 · Granted Nov 23, 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 11,179,336
App. No.
17/319,956
Granted
Nov 23, 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 (24)

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, 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 plurality of internal aqueous chambers of the MVLs has a pH of about 5.5;

wherein the bupivacaine concentration in the composition is from about 11.3 mg/mL to about 17.0 mg/mL, 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, and wherein the composition has a shelf life of up to 2 years when stored at 2-8° C.

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 lipid membranes further comprise cholesterol and tricaprylin.

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

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

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

13. The composition of claim 1 , wherein the composition comprises less than about 8% by weight unencapsulated bupivacaine when stored at 2-8° C. for up to 2 years.

14. 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%.

15. The composition of claim 1 , wherein the encapsulated bupivacaine is in a salt form.

16. The composition of claim 15 , wherein the encapsulated bupivacaine is in the form of bupivacaine phosphate.

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

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

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

20. The method of claim 14 , wherein the pain is postsurgical pain.

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 057537/0020 →
Cited By (1)
US 12,514,756