NZ503293A - Liposomal camptothecin formulations also comprising at least one phospholipid - Google Patents
Liposomal camptothecin formulations also comprising at least one phospholipidInfo
- Publication number
- NZ503293A NZ503293A NZ503293A NZ50329398A NZ503293A NZ 503293 A NZ503293 A NZ 503293A NZ 503293 A NZ503293 A NZ 503293A NZ 50329398 A NZ50329398 A NZ 50329398A NZ 503293 A NZ503293 A NZ 503293A
- Authority
- NZ
- New Zealand
- Prior art keywords
- liposome
- camptothecin
- cholesterol
- gradient
- aqueous medium
- Prior art date
Links
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 title abstract 3
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title abstract 3
- 229940127093 camptothecin Drugs 0.000 title abstract 3
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 title abstract 3
- 150000003904 phospholipids Chemical class 0.000 title abstract 2
- 238000009472 formulation Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 239000002502 liposome Substances 0.000 abstract 13
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 8
- 239000012736 aqueous medium Substances 0.000 abstract 4
- 235000012000 cholesterol Nutrition 0.000 abstract 4
- 150000002632 lipids Chemical class 0.000 abstract 3
- RVFGKBWWUQOIOU-NDEPHWFRSA-N lurtotecan Chemical compound O=C([C@]1(O)CC)OCC(C(N2CC3=4)=O)=C1C=C2C3=NC1=CC=2OCCOC=2C=C1C=4CN1CCN(C)CC1 RVFGKBWWUQOIOU-NDEPHWFRSA-N 0.000 abstract 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000012062 aqueous buffer Substances 0.000 abstract 1
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 230000000887 hydrating effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000010008 shearing Methods 0.000 abstract 1
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
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K9/1277—Processes for preparing; Proliposomes
- A61K9/1278—Post-loading, e.g. by ion or pH gradient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A liposome comprises at least one phospholipid and 7-(4-methylpiperazinomethylene)-10,11-ethylenedioxy-20(S)-camptothecin. The liposome may further comprise cholesterol. The liposome can encapsulate camptothecin wherein the liposome is comprised of hydrogenated soy phosphatidylcholine (HSPC) and cholesterol. The HSPC:cholesterol are in a molar ratio of about 2:1 and the lipid:camptothecin molar ratio is from 10:1 to 40:1. The liposome is unilamellar with an average size of less than 100nm The liposome can be produced by forming a lipid film or powder comprised of phosphatidylcholine and cholesterol, hydrating the lipid film or powder with an aqueous buffer containing a counterion solution. Applying a shearing force to obtain liposomes that are unilamellar and less than 100nm. Then 7-(4-methylpiperazinomethylene)-10,11-ethylenedioxy-20(S)-camptothecin is added to the aqueous medium. A gradient is generated between the aqueous medium inside the liposome and the aqueous medium external to the liposome whereby the gradient causes the 7-(4-methylpiperazinomethylene)-10,11-ethylenedioxy-20(S)-camptothecin to load into the liposome. The gradient may be a pH gradient. Further a membrane permeable amine may be added to the aqueous medium external to the liposome whereby the pH of the aqueous inside the liposome is decreased. The liposomes may be used in a pharmaceutical composition for inhibiting the growth of a tumor.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5908397P | 1997-09-16 | 1997-09-16 | |
| PCT/US1998/019086 WO1999013816A2 (en) | 1997-09-16 | 1998-09-15 | Liposomal camptothecin formulations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ503293A true NZ503293A (en) | 2002-09-27 |
Family
ID=22020747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ503293A NZ503293A (en) | 1997-09-16 | 1998-09-15 | Liposomal camptothecin formulations also comprising at least one phospholipid |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1037610A4 (en) |
| JP (1) | JP2003510239A (en) |
| KR (1) | KR100711315B1 (en) |
| AU (1) | AU751439B2 (en) |
| BR (1) | BR9812316A (en) |
| CA (1) | CA2303366A1 (en) |
| NZ (1) | NZ503293A (en) |
| WO (1) | WO1999013816A2 (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9914601A (en) | 1998-09-16 | 2001-10-23 | Alza Corp | Liposome-captured topoisomerase inhibitor |
| US7311924B2 (en) | 1999-04-01 | 2007-12-25 | Hana Biosciences, Inc. | Compositions and methods for treating cancer |
| US7244448B2 (en) * | 2000-06-30 | 2007-07-17 | Tekmira Pharmaceuticals Corporation | Liposomal antineoplastic drugs and uses thereof |
| US6613352B2 (en) | 1999-04-13 | 2003-09-02 | Universite De Montreal | Low-rigidity liposomal formulation |
| US7452550B2 (en) | 2000-06-30 | 2008-11-18 | Hana Biosciences, Inc. | Liposomal antineoplastic drugs and uses thereof |
| PL363618A1 (en) * | 2000-11-09 | 2004-11-29 | Neopharm, Inc. | Sn-38 lipid complexes and methods of use |
| DE10157994A1 (en) * | 2001-05-25 | 2003-01-02 | G O T Therapeutics Gmbh | Liposomally encapsulated hydrophobic active ingredients with a high active ingredient content> 50% and methods for producing pharmaceutical preparations which comprise liposomally encapsulated hydrophobic active ingredients |
| EP1393719A1 (en) * | 2002-08-23 | 2004-03-03 | Munich Biotech AG | Camptothecin-carboxylate formulations |
| EP1553924B1 (en) * | 2002-06-26 | 2010-12-08 | MediGene AG | Novel method of stabilizing diagnostic and therapeutic compounds in a cationic carrier system |
| US20040170677A1 (en) * | 2002-11-26 | 2004-09-02 | Ning Hu | Method of drug loading in liposomes by gradient |
| US20090285878A1 (en) * | 2004-11-05 | 2009-11-19 | Tekmira Pharmaceuticals Corporation | Compositions and methods for stabilizing liposomal drug formulations |
| WO2008070009A2 (en) * | 2006-12-01 | 2008-06-12 | Alza Corporation | Treating solid tumors and monocytic leukemia using topoisomerase inhibitors in liposomes |
| CN101209243B (en) | 2006-12-29 | 2010-12-08 | 石药集团中奇制药技术（石家庄）有限公司 | Liposome medicament and preparation thereof |
| TWI428135B (en) * | 2007-03-26 | 2014-03-01 | Hirofumi Takeuchi | And a carrier composition for quick-acting nucleic acid delivery |
| KR101130754B1 (en) | 2010-06-25 | 2012-03-28 | 제일약품주식회사 | Pharmaceutical compositions having improved solubility of poorly soluble tricyclic derivative compounds |
| AU2013203682B2 (en) * | 2011-08-25 | 2016-03-31 | Trophos | Liposome comprising at least one cholesterol derivative |
| FR2979239A1 (en) * | 2011-08-25 | 2013-03-01 | Trophos | LIPOSOME COMPRISING AT LEAST ONE CHOLESTEROL DERIVATIVE |
| WO2014047116A1 (en) * | 2012-09-18 | 2014-03-27 | Comfort Care For Animals Llc | Encapsulating liposomes |
| CN104837483B (en) | 2012-11-20 | 2017-09-01 | 光谱医药公司 | The improved method for preparing the liposome packaged type vincristine of therapeutical uses |
| TWI678213B (en) | 2015-07-22 | 2019-12-01 | 美商史倍壯製藥公司 | A ready-to-use formulation for vincristine sulfate liposome injection |
| KR102162351B1 (en) | 2018-11-08 | 2020-10-06 | 순천향대학교 산학협력단 | Drug-conjugated compound and uses thereof |
| CN115721610A (en) * | 2021-08-27 | 2023-03-03 | 沈阳药科大学 | 7-ethyl-10-hydroxycamptothecin compound liposome and preparation method and application thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5559235A (en) * | 1991-10-29 | 1996-09-24 | Glaxo Wellcome Inc. | Water soluble camptothecin derivatives |
| US5552156A (en) * | 1992-10-23 | 1996-09-03 | Ohio State University | Liposomal and micellular stabilization of camptothecin drugs |
| US5554382A (en) * | 1993-05-28 | 1996-09-10 | Aphios Corporation | Methods and apparatus for making liposomes |
| EP0721328A4 (en) * | 1993-09-27 | 1997-09-17 | Smithkline Beecham Corp | Camptothecin formulations |
-
1998
- 1998-09-15 AU AU93877/98A patent/AU751439B2/en not_active Ceased
- 1998-09-15 JP JP2000511445A patent/JP2003510239A/en active Pending
- 1998-09-15 NZ NZ503293A patent/NZ503293A/en unknown
- 1998-09-15 EP EP98946983A patent/EP1037610A4/en not_active Withdrawn
- 1998-09-15 CA CA002303366A patent/CA2303366A1/en not_active Abandoned
- 1998-09-15 BR BR9812316-5A patent/BR9812316A/en not_active Application Discontinuation
- 1998-09-15 WO PCT/US1998/019086 patent/WO1999013816A2/en not_active Application Discontinuation
- 1998-09-15 KR KR1020007002701A patent/KR100711315B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100711315B1 (en) | 2007-04-27 |
| EP1037610A1 (en) | 2000-09-27 |
| BR9812316A (en) | 2001-03-20 |
| AU751439B2 (en) | 2002-08-15 |
| WO1999013816A3 (en) | 2001-11-01 |
| AU9387798A (en) | 1999-04-05 |
| JP2003510239A (en) | 2003-03-18 |
| WO1999013816A2 (en) | 1999-03-25 |
| KR20010030599A (en) | 2001-04-16 |
| EP1037610A4 (en) | 2004-07-07 |
| CA2303366A1 (en) | 1999-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |