IP Library Granted Patent US 10,028,911
Granted Patent B2
US 10,028,911 · App. 13/786,323 · Granted Jul 24, 2018

Sustained release formulation of methotrexate as a disease-modifying antirheumatic drug (DMARD) and an anti-cancer agent

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Quick Facts
Patent No.
US 10,028,911
App. No.
13/786,323
Granted
Jul 24, 2018
Kind
B2
Abstract

Disclosed is are formulations comprising a multivesicular liposome and MTX, the administration of which results in a C max of MTX between 5% and 50% of the C max of an immediate release dosage form of MTX, the duration of which lasts from about 1 to about 30 days. Also disclosed are methods of treating autoimmune diseases and cancer by administering these formulations of MTX.

Claims (24)

1. A formulation comprising multivesicular liposomes for administration by injection, said multivesicular liposomes comprise an amount of a basic addition salt of methotrexate, one or more amphipathic lipids or salts thereof, one or more neutral lipids, and optionally cholesterol or plant sterols, wherein the formulation is substantially cyclodextrin free, wherein administration of a single dose of said formulation to a subject in need thereof results in a plasma C max of said methotrexate of from 5% to 50% of the plasma C max of immediate release dosage forms of methotrexate, and wherein a duration of said methotrexate in the subject is from about 1 to about 30 days.

2. The formulation as in claim 1 , wherein the basic addition salt of methotrexate is a sodium salt.

3. The formulation as in claim 1 , wherein the basic addition salt of methotrexate is a potassium salt.

4. The formulation as in claim 1 , wherein the basic addition salt of methotrexate comprises an organic base as a counter ion.

5. The formulation as in claim 1 , wherein the multivesicular liposome further comprises a Folate to decrease C max -related side effects.

6. The formulation as in claim 1 , wherein the multivesicular liposome comprises cholesterol, one or more amphipathic lipids or salts thereof, and one or more triglycerides.

7. The formulation as in claim 6 , wherein said one or more amphipathic lipids are selected from one or more phosphatidylcholines, one or more phosphatidylglycerols or salts thereof, or combinations thereof.

8. The formulation as in claim 7 , wherein the phosphatidylglycerol comprises DPPG.

9. The formulation as in claim 7 , wherein the phosphatidylcholine comprises DEPC.

10. The formulation as in claim 7 , wherein the phosphatidylcholine comprises DOPC.

11. The formulation as in claim 6 , wherein said one or more triglycerides are selected from triolein, tricaprylin, or a combination of the two.

12. The formulation as in claim 1 , wherein the multivesicular liposome further comprises lysine.

13. The formulation as in claim 1 , wherein the duration of the methotrexate plasma levels is about 1 day to 7 days.

14. The formulation as in claim 1 , wherein the formulation is stable for at least two years.

15. The formulation as in claim 1 , wherein the formulation can be delivered through needle gauges of 27-31G.

16. The formulation as in claim 1 , wherein the concentration of cholesterol in said formulation is from about 5 to about 80 mM in an organic solvent solution that forms a first water-in-oil (w/o) emulsion.

17. The formulation as in claim 7 , wherein the concentration of phosphatidylcholines in said formulation is from about 5 to about 50 mM in an organic solvent solution that forms a first water-in-oil (w/o) emulsion.

18. The formulation as in claim 7 , wherein the concentration of phosphatidylglycerol in said formulation is from about 0 to about 15 mM in an organic solvent solution that forms a first water-in-oil (w/o) emulsion.

19. The formulation as in claim 11 , wherein the concentration of triolein is from about 0 to about 8 mM in an organic solvent solution that forms a first water-in-oil (w/o) emulsion.

20. The formulation as in claim 11 , wherein the concentration of tricaprylin is from about 5 to about 80 mM in an organic solvent solution that forms a first water-in-oil (w/o) emulsion.

21. The formulation as in claim 1 , wherein the plasma C max of said methotrexate of from 5% to about 35% of the plasma C max of immediate release dosage forms of methotrexate.

22. The formulation as in claim 1 , wherein the plasma C max of said methotrexate of from 5% to about 11% of the plasma C max of immediate release dosage forms of methotrexate.

23. The formulation as in claim 1 , wherein the molar ratio of said one or more amphipathic lipids to said one or more neutral lipids is about 4 to 5.

24. The formulation as in claim 1 , wherein the molar ratio of said one or more amphipathic lipids to said one or more neutral lipids is about 9 to 11.

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 Jan 10, 2018
From: GARCIA, LOUIE DANIEL; GIBSON, LOIS; LAMBERT, WILLIAM; LI, BENJAMIN; ZHU, LIANGJIN
To: PACIRA PHARMACEUTICALS, INC.
Reel/Frame 044584/0633 →