CA2644198A1 - Pharmaceutical latrunculin formulations - Google Patents
Pharmaceutical latrunculin formulations Download PDFInfo
- Publication number
- CA2644198A1 CA2644198A1 CA002644198A CA2644198A CA2644198A1 CA 2644198 A1 CA2644198 A1 CA 2644198A1 CA 002644198 A CA002644198 A CA 002644198A CA 2644198 A CA2644198 A CA 2644198A CA 2644198 A1 CA2644198 A1 CA 2644198A1
- Authority
- CA
- Canada
- Prior art keywords
- latrunculin
- pharmaceutical formulation
- aqueous pharmaceutical
- formulation
- buffer
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 238000009472 formulation Methods 0.000 title claims abstract description 84
- 229930193708 latrunculin Natural products 0.000 title claims abstract description 76
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 78
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000012929 tonicity agent Substances 0.000 claims abstract description 30
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- 239000004094 surface-active agent Substances 0.000 claims abstract description 21
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- NSHPHXHGRHSMIK-IWQSFCKSSA-N latrunculin B Natural products C[C@H]1CC[C@@H]2C[C@@H](C[C@@](O)(O2)[C@@H]3CSC(=O)N3)OC(=O)C=C(C)/CCC=C/1 NSHPHXHGRHSMIK-IWQSFCKSSA-N 0.000 claims description 43
- 239000000872 buffer Substances 0.000 claims description 36
- NSHPHXHGRHSMIK-JRIKCGFMSA-N latrunculin B Chemical compound C([C@H]1[C@@]2(O)C[C@H]3C[C@H](O2)CC[C@@H](\C=C/CC\C(C)=C/C(=O)O3)C)SC(=O)N1 NSHPHXHGRHSMIK-JRIKCGFMSA-N 0.000 claims description 32
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 13
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
- 239000008351 acetate buffer Substances 0.000 claims description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 8
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- 229940075507 glyceryl monostearate Drugs 0.000 claims description 3
- DDVBPZROPPMBLW-UHFFFAOYSA-N latrunculin-A Natural products O1C(=O)C=C(C)CCC=CC=CC(C)CCC(O2)CC1CC2(O)C1CSC(=O)N1 DDVBPZROPPMBLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 3
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 3
- 229960004224 tyloxapol Drugs 0.000 claims description 3
- 229920001664 tyloxapol Polymers 0.000 claims description 3
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 claims description 3
- 229950008882 polysorbate Drugs 0.000 claims description 2
- 229940068965 polysorbates Drugs 0.000 claims description 2
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 2
- DDVBPZROPPMBLW-ZJBINBEQSA-N latrunculin a Chemical compound C([C@H]1[C@@]2(O)C[C@H]3C[C@H](O2)CC[C@@H](/C=C\C=C/CC\C(C)=C/C(=O)O3)C)SC(=O)N1 DDVBPZROPPMBLW-ZJBINBEQSA-N 0.000 claims 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 description 12
- 229960000686 benzalkonium chloride Drugs 0.000 description 11
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 11
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
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Classifications
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
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- A—HUMAN NECESSITIES
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- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- 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
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- A61K9/0048—Eye, e.g. artificial tears
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- A—HUMAN NECESSITIES
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- A61K9/00—Medicinal preparations characterised by special physical form
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77927306P | 2006-03-02 | 2006-03-02 | |
| US60/779,273 | 2006-03-02 | ||
| US11/680,893 | 2007-03-01 | ||
| US11/680,893 US7785624B2 (en) | 2006-03-02 | 2007-03-01 | Pharmaceutical latrunculin formulations |
| PCT/US2007/063171 WO2007103782A2 (en) | 2006-03-02 | 2007-03-02 | Pharmaceutical latrunculin formulations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2644198A1 true CA2644198A1 (en) | 2007-09-13 |
Family
ID=38475717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002644198A Abandoned CA2644198A1 (en) | 2006-03-02 | 2007-03-02 | Pharmaceutical latrunculin formulations |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7785624B2 (https=) |
| EP (1) | EP1993563A4 (https=) |
| JP (1) | JP2009528390A (https=) |
| KR (1) | KR20080098636A (https=) |
| AU (1) | AU2007223378A1 (https=) |
| BR (1) | BRPI0708483A2 (https=) |
| CA (1) | CA2644198A1 (https=) |
| MX (1) | MX2008011112A (https=) |
| RU (1) | RU2434633C2 (https=) |
| WO (1) | WO2007103782A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010014240A2 (en) * | 2008-07-29 | 2010-02-04 | The Regents Of The University Of California | Novel bioactive small molecules derived from sea sponges |
| US11254792B2 (en) | 2015-12-29 | 2022-02-22 | Galderma Holding SA | Method for deacetylation of biopolymers |
| JP7386080B2 (ja) * | 2016-08-02 | 2023-11-24 | アンバー アイピー リミテッド | 安定なイブプロフェン注射製剤用組成物 |
| US20220047719A1 (en) * | 2020-08-17 | 2022-02-17 | Northwestern University | Enhancing subcutaneous injection and target tissue accumulation of nanoparticles via co-administration with macropinocytosis inhibitory nanoparticles (minp) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2052950A1 (en) | 1990-10-10 | 1992-04-11 | David P. Evitts | Aqueous ophthalmic microemulsions of tepoxalin |
| US5422116A (en) | 1994-02-18 | 1995-06-06 | Ciba-Geigy Corporation | Liquid ophthalmic sustained release delivery system |
| US5798380A (en) | 1996-02-21 | 1998-08-25 | Wisconsin Alumni Research Foundation | Cytoskeletal active agents for glaucoma therapy |
| US6586425B2 (en) | 1996-02-21 | 2003-07-01 | Wisconsin Alumni Research Foundation | Cytoskeletal active agents for glaucoma therapy |
| JP3677421B2 (ja) * | 1999-12-27 | 2005-08-03 | 扶桑薬品工業株式会社 | 涙液分泌促進組成物 |
| US20030165545A1 (en) * | 2002-01-30 | 2003-09-04 | Allergan, Inc. | Ophthalmic compositions including oil-in-water emulsions, and methods for making and using same |
| CN101160315A (zh) * | 2005-03-25 | 2008-04-09 | 印斯拜尔药品股份有限公司 | 细胞骨架的活性化合物，组合物及用途 |
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2007
- 2007-03-01 US US11/680,893 patent/US7785624B2/en not_active Expired - Fee Related
- 2007-03-02 RU RU2008139113/15A patent/RU2434633C2/ru not_active IP Right Cessation
- 2007-03-02 JP JP2008557515A patent/JP2009528390A/ja not_active Withdrawn
- 2007-03-02 KR KR1020087021403A patent/KR20080098636A/ko not_active Withdrawn
- 2007-03-02 CA CA002644198A patent/CA2644198A1/en not_active Abandoned
- 2007-03-02 MX MX2008011112A patent/MX2008011112A/es active IP Right Grant
- 2007-03-02 EP EP07757790A patent/EP1993563A4/en not_active Withdrawn
- 2007-03-02 AU AU2007223378A patent/AU2007223378A1/en not_active Abandoned
- 2007-03-02 WO PCT/US2007/063171 patent/WO2007103782A2/en not_active Ceased
- 2007-03-02 BR BRPI0708483-8A patent/BRPI0708483A2/pt not_active IP Right Cessation
-
2010
- 2010-08-13 US US12/856,412 patent/US20100305175A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7785624B2 (en) | 2010-08-31 |
| EP1993563A2 (en) | 2008-11-26 |
| US20070225343A1 (en) | 2007-09-27 |
| JP2009528390A (ja) | 2009-08-06 |
| KR20080098636A (ko) | 2008-11-11 |
| RU2434633C2 (ru) | 2011-11-27 |
| WO2007103782A2 (en) | 2007-09-13 |
| US20100305175A1 (en) | 2010-12-02 |
| BRPI0708483A2 (pt) | 2011-05-31 |
| MX2008011112A (es) | 2008-09-08 |
| EP1993563A4 (en) | 2009-05-20 |
| RU2008139113A (ru) | 2010-04-10 |
| WO2007103782A3 (en) | 2008-03-20 |
| AU2007223378A1 (en) | 2007-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130304 |