CA2512487A1 - Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof - Google Patents

Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof Download PDF

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Publication number
CA2512487A1
CA2512487A1 CA002512487A CA2512487A CA2512487A1 CA 2512487 A1 CA2512487 A1 CA 2512487A1 CA 002512487 A CA002512487 A CA 002512487A CA 2512487 A CA2512487 A CA 2512487A CA 2512487 A1 CA2512487 A1 CA 2512487A1
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CA
Canada
Prior art keywords
particles
protein
paclitaxel
pharmacologically active
delivery system
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002512487A
Other languages
French (fr)
Other versions
CA2512487C (en
Inventor
Neil P. Desai
Chunlin Tao
Andrew Yang
Leslie Louie
Tianli Zheng
Zhiwen Yao
Patrick Soon-Shiong
Shlomo Magdassi
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Abraxis Bioscience LLC
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Individual
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Application filed by Individual filed Critical Individual
Publication of CA2512487A1 publication Critical patent/CA2512487A1/en
Application granted granted Critical
Publication of CA2512487C publication Critical patent/CA2512487C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/513—Organic macromolecular compounds; Dendrimers
    • A61K9/5169—Proteins, e.g. albumin, gelatin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5192—Processes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • 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
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
    • Y10S977/906—Drug delivery
    • Y10S977/907—Liposome
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
    • Y10S977/915—Therapeutic or pharmaceutical composition
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
    • Y10S977/927—Diagnostic contrast agent

Abstract

In accordance with the present invention, there are provided compositions and methods useful for the in vivo delivery of substantially water-insoluble pharmacologically active agents (such as the anticancer drug paclitaxel) in which the pharmacologically active agent is delivered in the form of suspended particles coated with protein (which acts as a stabilizing agent). In particular, protein and pharmacologically active agent in a biocompatible dispersing medium are subjected to high shear, in the absence of any conventional surfactants, and also in the absence of any polymeric core material for the particles. The procedure yields particles with a diameter of less than about 1 micron.
The use of specific composition and preparation conditions (e.g., addition of a polar solvent to the organic phase), and careful selection of the proper phase and phase fraction, enables the reproducible production of unusually small nanoparticles of less than 200 nm diameter, which can be sterile-filtered. The particulate system produced according to the invention can be converted into a redispersible dry powder comprising nanoparticles of water-insoluble drug coated with a protein, and free protein to which molecules of the pharmacological agent are bound. This results in a unique delivery system, in which part of the pharmacologically active agent is readily bioavailable (in the form of molecules bound to the protein), and part of the agent is present within particles without any polymeric matrix therein.

Claims (26)

1. A drug delivery system comprising particles of a solid or liquid, substantially water insoluble pharmacologically active agent, coated with protein, wherein said protein coating has free protein associated therewith, wherein a portion of said pharmacologically active agent is contained within said protein coating and a portion of said pharmacologically active agent is associated with said free protein, and wherein the average diameter of said particles is no greater than about 1 micron.
2. A drug delivery system according to claim 1 wherein the average diameter of said particles is less than 200 nm.
3. A drug delivery system according to claim 2 wherein said system is sterile filtered.
4. A drug delivery system according to claim 1 wherein said particles are amorphous, crystalline, or a mixture thereof.
5. A drug delivery system according to claim 9 wherein said particles are substantially amorphous.
6. A drug delivery system according to claim 1 wherein said protein shell is suspended in a biocompatible aqueous liquid.
7. A method for the delivery of substantially water insoluble pharmaceutical agents to a subject, said method comprising administering to said subject an effective amount of said pharmaceutical agent as part of a delivery system according to claim 1.
8. A method to reduce the myelosuppressive effect of pharmaceutical agents, said method comprising administering an effective amount of said pharmaceutical agent as part of a drug delivery system according to claim 1.
9. A method according to claim 8 wherein said pharmaceutical agent is paclitaxel and said protein is albumin.
10. A method for eliminating cancer cells with a cremaphor free oncolytic comprising particles of an antineoplastic coated with protein, wherein said protein coating has free protein associated therewith, wherein a portion of said antineoplastic is contained within said protein coating and a portion of said antineoplastic is associated with said free protein, and wherein the average diameter of said particles is no greater than about 1 micron.
11. A method according to claim 10 wherein the average diameter of said particles is less than 200 nm.
12. A method according to claim 11 wherein said system is sterile filtered.
13. A method according to claim 10 wherein said particles are amorphous, crystalline, or a mixture thereof.
14. A method according to claim 13 wherein said particles are substantially amorphous.
15. A method according to claim 10 wherein said antineoplastic is paclitaxel and said protein is albumin.
16. Bioprotected particles of a substantially water insoluble pharmacologically active agent coated with protein, wherein said particles are surrounded by free protein associated therewith, wherein a portion of said pharmacologically active agent is contained within said protein coating and a portion of said pharmacologically active agent is associated with said free protein surrounding said protein coating, and wherein the average diameter of said particles is no greater than about 1 micron.
17. Bioprotected particles according to claim 16 wherein the average diameter of said particles is less than 200 nm.
18. Bioprotected particles according to claim 17 wherein said particles are sterile filtered.
19. Bioprotected particles according to claim 16 wherein said particles are amorphous, crystalline, or a mixture thereof.
20. Bioprotected particles according to claim 19 wherein said particles are substantially amorphous.
21. Bioprotected particles according to claim 16 wherein said pharmacologically active agent is paclitaxel and said ptrotein is albumin.
22. A method for reducing liver sequestration of pharmaceutical agents, said method comprising administering an effective amount of said pharmaceutical agent as part of a drug delivery system according to claim 1.
23. A method according to claim 22 wherein said pharmaceutical agent is paclitaxel and said protein is albumin.
24. A method for the administration of paclitaxel to a patient in need thereof employing a dosing solution containing > 1 mg/ml of paclitaxel, said method comprising administering said paclitaxel as part of a drug delivery system according to claim 1.
25. A method for the administration of paclitaxel to a patient in need thereof employing a total infusion volume for each effective dose of < 300 ml of paclitaxel-containing medium, said method comprising administering said paclitaxel as part of a drug delivery system according to claim 1.
26. A method for the rapid administration of paclitaxel to a patient in need thereof, said method comprising administering said paclitaxel as part of a drug delivery system according to claim 1.
CA2512487A 1996-10-01 1997-09-24 Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof Expired - Lifetime CA2512487C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/720,756 1996-10-01
US08/720,756 US5916596A (en) 1993-02-22 1996-10-01 Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof
CA002267498A CA2267498C (en) 1996-10-01 1997-09-24 Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002267498A Division CA2267498C (en) 1996-10-01 1997-09-24 Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof

Publications (2)

Publication Number Publication Date
CA2512487A1 true CA2512487A1 (en) 1998-04-09
CA2512487C CA2512487C (en) 2012-05-29

Family

ID=24895164

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2512487A Expired - Lifetime CA2512487C (en) 1996-10-01 1997-09-24 Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof
CA002267498A Expired - Lifetime CA2267498C (en) 1996-10-01 1997-09-24 Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA002267498A Expired - Lifetime CA2267498C (en) 1996-10-01 1997-09-24 Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof

Country Status (19)

Country Link
US (1) US5916596A (en)
EP (3) EP1944019B1 (en)
JP (2) JP4837809B2 (en)
CN (2) CN1515244B (en)
AT (1) ATE427739T1 (en)
AU (1) AU718753B2 (en)
BR (2) BRPI9711856B8 (en)
CA (2) CA2512487C (en)
DE (2) DE69739348D1 (en)
DK (1) DK0961612T4 (en)
ES (2) ES2609853T3 (en)
FR (1) FR09C0050I2 (en)
HK (1) HK1024866A1 (en)
LU (1) LU91613I2 (en)
NL (1) NL300417I1 (en)
NO (1) NO328689B1 (en)
NZ (1) NZ335133A (en)
PT (1) PT961612E (en)
WO (1) WO1998014174A1 (en)

Cited By (1)

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PT106738A (en) * 2013-01-09 2014-07-09 Hovione Farmaciencia Sa DYNAMIC DRYING OF SUSPENSIONS FOR THE CONTROL OF OSTWALD DIFUSIONAL DEGRADATION PHENOMENON (OSTWALD RIPENING)

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