CA2505520A1 - Protein-stabilized liposomal formulations of pharmaceutical agents - Google Patents

Protein-stabilized liposomal formulations of pharmaceutical agents Download PDF

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Publication number
CA2505520A1
CA2505520A1 CA002505520A CA2505520A CA2505520A1 CA 2505520 A1 CA2505520 A1 CA 2505520A1 CA 002505520 A CA002505520 A CA 002505520A CA 2505520 A CA2505520 A CA 2505520A CA 2505520 A1 CA2505520 A1 CA 2505520A1
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agent
protein
pharmaceutical agent
emulsion
lipid
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CA2505520C (en
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Chandra U. Singh
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Azaya Therapeutics Inc
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1277—Processes for preparing; Proliposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • A—HUMAN NECESSITIES
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    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
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    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes

Abstract

The present invention relates to protein stabilized liposomes. Specifically, the present invention discloses compositions and methods for protein stabilized liposomes, the creation of protein stabilized liposomes, and the administration of protein stabilized liposomes.

Claims (38)

1. A method of preparing a protein-stabilized lipid formulation containing at least one lipophilic pharmaceutical agent, the method comprising:
(a) preparing an organic solution comprising one or more phospholipids;
(b) mixing at least one pharmaceutical agent into said organic solution;
(c) infusing said organic mixture into an aqueous solution comprising an emulsion-forming protein to form an emulsion; and (d) removing organic solvent from said emulsion to form the protein-stabilized lipid formulation.
2. The method of claim 1, wherein the lipid formulation comprises protein-stabilized liposomes.
3. The method of claim 2, wherein the liposome-forming components further includes cholesterol.
4. The method of claim 2, wherein the liposome-forming components further includes a PEG-phospholipid.
5. The method of claim 4, wherein said PEG-phospholipid comprises poly(ethylene glycol)-derivatized distearoylphosphatidylethanolamine (PEG-DSPE) and/or poly(ethylene glycol)-derivatized ceramides (PEG-CER)
6. The method of claim 1, wherein the lipophilic pharmaceutical agent is further identified as a substantially water insoluble pharmaceutical agent.
7. The method of claim 1, wherein the phospholipid and lipophilic pharmaceutical agent are included in the organic solution at a ratio ranging from about 0.01:25 to about 1:10 drug:lipid (w/w).
8. The method of claim 1 wherein said emulsion forming protein comprises an albumin, immunoglobulin, casein, insulin, hemoglobin, lysozyme, immunoglobulin, .alpha.-macroglobulin, fibronectin, vitronectin, fibrinogen, lipase, or enzyme.
9. The method of claim 8, wherein the emulsion forming protein is an albumin.
10. The method of claim 1, wherein said aqueous solution is at a pH of between about 6.0 and 7.6.
11. The method of claim 1, wherein said emulsion-forming protein comprises from about 0.1% to about 20% (w/v) of the aqueous solution.
12. The method of claim 11, wherein said emulsion-forming protein comprises from about 1% to about 10% (w/v) of the aqueous solution.
13. The method of claim 1, wherein the emulsion is formed by steps that comprise:
(a) agitating said mixture at between about 1000 and about 24,000 revolutions per minute;
and (b) subjecting the agitated mixture to high pressure microfluidization or homogenization at 5,000 to 30,000 PSI.
14. The method of claim 13, wherein the emulsion is formed by steps that comprise:
(a) agitating said mixture at between about 3000 and about 10,000 revolutions per minute;
and (b) subjecting the agitated mixture to high pressure microfluidization or homogenization at 10,000 to 30,000 PSI.
15. The method of claim 13, wherein the mixture is agitated using a homogenizer.
16. The method of claim 15, wherein the mixture is agitated using a rotary homogenizer.
17. The method of claim 1, wherein the lipid formulation is filtered.
18. The method of claim 17, wherein the lipid formulation is filtered through a 0.20 or 0.22 micron filter.
19. The method of claim 1, wherein the lipid formulation is lyophilized to provide a powder suitable for reconstitution in an aqueous suspension.
20. The method of claim 19, wherein the lipid formulation is lyophilized in the presence of one or more cryoprotectants.
21. The method of claim 20 wherein the cryoprotectant is sucrose, mannitol or trehalose.
22. The method of claim 1 wherein the pharmaceutical agent comprises a cardiovascular drug, respiratory drug, sympathomimetic drug, cholinomimetic drug, adrenergic or adrenergic neuron blocking drug, analgesic/antipyretic, anesthetic, antiasthamatic, antibiotic, antidepressant, antidiabetic, antifungal agent, antihypertensive agent, anti-inflammatory, antineoplastic, antianxiety agent, immunosuppressive agent, antimigraine agent, sedatives/hypnotic, antianginal agent, antipsychotic agent, antimanic agent, antiarrhythmic, antiarthritic agent, antigout agent, anticoagulant, thrombolytic agent, antifibrinolytic agent, hemorheologic agent, antiplatelet agent, anticonvulsant, antiparkinson agent, antihistamine/antipruritic, agent useful for calcium regulation, antibacterial agent, antiviral agent, antimicrobial, anti-infective, bronchodialator, hormone, hypoglycemic agent, hypolipidemic agent, protein, nucleic acid, agent useful for erythropoiesis stimulation, antiulcer/antireflux agent, antinauseant/antiemetic, oil-soluble vitamin, mitotane, visadine, halonitrosourea, anthrocycline or ellipticine.
23. The method of claim 22, wherein the pharmaceutical agent is Proscillaridin-A, oleandrin, digitoxin, digoxin, odoroside-A, colchicine, colchicine derivatives, ara-C
derivatives, diphyllin, justicidin-A, diphyllin derivatives, cleistanthin A, chloroquine, amphotericin B, paclitaxel, docetaxel, cyclosporine, camptothecin, 7-ethyl-10-hydroxy-camptothecin, 10-hydroxy-camptothecin, a camptothecin derivative, podophyllotoxin, podophyllotoxin derivatives, vinblastine, vincristine, dihydroartemisinin, mitoxantrone, amphotericin B, epothilone-A, epothilone-B, epothilone-C, epothilone-D, an epothilone derivative, a benz[c]-phenanthridine alkaloid derivative, a chelerythrine alkaloid derivative or cisplatin.
24. The method of claim 1, wherein said one or more phospholipids comprise one or more of hydrogenated soy phosphatidylcholine (HSPC), egg phosphatidylcholine (EPC), phosphatidylethanolamine (PE), phosphatidylglycerol (PG), phosphatidylinsitol (PI) monosialogangolioside, spingomyelin (SPM), distearoylphosphatidylcholine (DSPC), dimyristoylphosphatidylcholine (DMPC), or dimyristoylphosphatidylglycerol (DMPG).
25. The method of claim 1, wherein the ratio of pharmaceutical agent to lipid-protein ranges from about 0.0005 to about 1 (w/w).
26. The method of claim 25, wherein the ratio of pharmaceutical agent to lipid-protein ranges from about 0.0005 to about 0.5 (w/w).
27. The method of claim 26, wherein the ratio of pharmaceutical agent to lipid-protein ranges from about 0.001 to about 0.1 (w/w).
28. The method of claim 1, wherein the lipid formulation is subjected to high shear stress to reduce particle size.
29. The method of claim 1, wherein the lipid formulation is defined further as comprising nanoparticles having size less than about 220 nm.
30. The method of claim 29, wherein the nanoparticles have a size of between about 80-160 nm.
31. The method of claim 30, wherein the nanoparticles have a size of between about 100-120 nm.
32. A protein-stabilized lipid formulation comprising a lipophilic pharmaceutical agent, the formulation prepared by the process of any one of claim 1 - 31.
33. A method of treating a disease in a patient comprising:
(a) obtaining a lipophilic pharmaceutical agent drug indicated for treatment of the disease;
(b) preparing a protein-stabilized lipid formulation of said pharmaceutical agent; and (c) administering an amount of the lipid formulated pharmaceutical agent to said patient that is effective to treat the disease.
34. The method of claim 33, wherein the protein-stabilized lipid formulation of said pharmaceutical agent is prepared in accordance with claim 1.
35. The method of claim 33, wherein the disease is a hyperproliferative disease and the pharmaceutical agent is an anti-hyperproliferative agent.
36. The method of claim 33, wherein the formulation is administered parenterally.
37. The method of claim 36, wherein the formulation is administered by slow infusion or bolus injection.
38
CA2505520A 2002-11-06 2003-11-06 Protein-stabilized liposomal formulations of pharmaceutical agents Expired - Lifetime CA2505520C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US42423002P 2002-11-06 2002-11-06
US60/424,230 2002-11-06
PCT/US2003/035297 WO2004043363A2 (en) 2002-11-06 2003-11-06 Protein-stabilized liposomal formulations of pharmaceutical agents

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CA2505520A1 true CA2505520A1 (en) 2004-05-27
CA2505520C CA2505520C (en) 2012-07-17

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US (2) US7179484B2 (en)
EP (1) EP1585504A4 (en)
JP (1) JP2006508126A (en)
AU (1) AU2003287526A1 (en)
CA (1) CA2505520C (en)
WO (1) WO2004043363A2 (en)

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