IP Library Granted Patent US 11,185,506
Granted Patent B1
US 11,185,506 · App. 17/319,591 · Granted Nov 30, 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 11,185,506
App. No.
17/319,591
Granted
Nov 30, 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 (27)

1. A process for preparing bupivacaine encapsulated multivesicular liposomes in a commercial scale, 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, at least one amphipathic lipid comprising 1, 2-dierucoylphosphatidylcholine (DEPC), 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 multivesicular liposomes having a first volume;

(d) reducing the first volume of the first aqueous suspension of bupivacaine encapsulated multivesicular liposomes by microfiltration to provide a second aqueous suspension of bupivacaine encapsulated multivesicular liposomes 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 multivesicular liposomes 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 multivesicular liposomes having a target concentration of bupivacaine from about 11.3 mg/mL to about 17.0 mg/mL;

wherein all steps are carried out under aseptic conditions;

wherein the erucic acid concentration in the final aqueous suspension of bupivacaine encapsulated multivesicular liposomes is about 23 μg/mL or less after the final aqueous suspension is stored at 25° C. for one month;

wherein the final aqueous suspension of bupivacaine encapsulated multivesicular liposomes has a volume of about 150 L to about 250 L; and

wherein the internal pH of the bupivacaine encapsulated multivesicular liposomes in the final aqueous suspension is about 5.5.

2. The process of claim 1 , wherein the mixing of step (a) is performed using a mixer at a high shear speed from about 1100 rpm to about 1200 rpm.

3. The process of claim 2 , wherein the high shear speed is about 1150 rpm.

4. The process of claim 1 , wherein the mixing of step (a) is performed for about 65-75 minutes.

5. The process of claim 1 , wherein the mixing of step (b) is performed using two mixers at a low shear speed from about 450 rpm to about 510 rpm.

6. The process of claim 5 , wherein the low shear speed is about 495 rpm.

7. The process of claim 1 , wherein the mixing of step (b) is performed for about 60 to 65 seconds.

8. The process of claim 1 , wherein step (e) is performed using two sets of filtration modules, wherein each set of the filtration modules operate independently of the other.

9. The process of claim 8 , where each set of filtration modules comprise five or more individual hollow fiber filters, wherein each individual hollow fiber filter has a membrane pore size from about 0.1 μm to about 0.2 μm.

10. The process of claim 1 , wherein the final aqueous suspension of bupivacaine encapsulated multivesicular liposomes has a volume of about 200 L to about 225 L.

11. The process of claim 1 , wherein the target concentration of bupivacaine in the final aqueous suspension of bupivacaine encapsulated multivesicular liposomes is about 13.3 mg/mL.

12. The process of claim 1 , wherein the final aqueous suspension of bupivacaine encapsulated multivesicular liposomes comprises less than 5% unencapsulated bupivacaine.

13. The process of claim 1 , wherein the d 50 of bupivacaine encapsulated multivesicular liposomes in the final aqueous suspension is about 24 μm to about 31 μm.

14. The process of claim 13 , wherein the d 50 of bupivacaine encapsulated multivesicular liposomes in the final aqueous suspension is about 27 μm.

15. The process of claim 1 , wherein the encapsulated lysine concentration of bupivacaine multivesicular liposomes in the final aqueous suspension is about 0.03 mg/mL.

16. The process of claim 1 , wherein final aqueous suspension of bupivacaine encapsulated multivesicular liposomes is suitable for direct human administration.

17. The process of claim 1 , wherein the volatile water-immiscible solvent solution of step (a) further comprises 1,2-dipalmitoyl-sn-glycero-3 phospho-rac-(1-glycerol) (DPPG).

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 →
Continuity (1)
Continuation 17156400 · Jan 22, 2021
Cited By (9)
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