CA2554346C - Parenteral formulations comprising a beta-cyclodextrin and a preservative - Google Patents
Parenteral formulations comprising a beta-cyclodextrin and a preservative Download PDFInfo
- Publication number
- CA2554346C CA2554346C CA002554346A CA2554346A CA2554346C CA 2554346 C CA2554346 C CA 2554346C CA 002554346 A CA002554346 A CA 002554346A CA 2554346 A CA2554346 A CA 2554346A CA 2554346 C CA2554346 C CA 2554346C
- Authority
- CA
- Canada
- Prior art keywords
- cyclodextrin
- preservative
- pharmaceutical composition
- compound
- formula
- 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.)
- Expired - Lifetime
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 144
- 239000003755 preservative agent Substances 0.000 title claims abstract description 134
- 230000002335 preservative effect Effects 0.000 title claims abstract description 117
- 239000000203 mixture Substances 0.000 title claims description 115
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims description 4
- 238000009472 formulation Methods 0.000 title description 82
- 239000001116 FEMA 4028 Substances 0.000 title description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 title description 2
- 229960004853 betadex Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 146
- 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 abstract description 84
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 80
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical group CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 108
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- 150000003839 salts Chemical class 0.000 claims description 32
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 claims description 21
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- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical group O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims description 7
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- VNDHXHMRJVTMTK-WZVRVNPQSA-H hexasodium 4-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10-(hydroxymethyl)-15,20,25,30,35-pentakis(4-sulfonatobutoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methoxy]butane-1-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]1[C@H](O)[C@H]2O VNDHXHMRJVTMTK-WZVRVNPQSA-H 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 claims 1
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- -1 NaCI Chemical class 0.000 description 16
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
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- SIYLLGKDQZGJHK-UHFFFAOYSA-N dimethyl-(phenylmethyl)-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethyl]ammonium Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 SIYLLGKDQZGJHK-UHFFFAOYSA-N 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
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- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
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- 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
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
-
- 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
- A61K47/08—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
-
- 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
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
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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
- A61K9/0012—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/10—Antimycotics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nanotechnology (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medical Informatics (AREA)
- Communicable Diseases (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54089704P | 2004-01-30 | 2004-01-30 | |
| US60/540,897 | 2004-01-30 | ||
| PCT/IB2005/000100 WO2005082416A2 (en) | 2004-01-30 | 2005-01-17 | Antimicrobial preservatives to achieve multi-dose formulation using beta-cyclodextrins for liquid dosage forms |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2554346A1 CA2554346A1 (en) | 2005-09-09 |
| CA2554346C true CA2554346C (en) | 2009-11-17 |
Family
ID=34910697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002554346A Expired - Lifetime CA2554346C (en) | 2004-01-30 | 2005-01-17 | Parenteral formulations comprising a beta-cyclodextrin and a preservative |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US8183230B2 (enExample) |
| EP (1) | EP1713504B1 (enExample) |
| JP (1) | JP5021318B2 (enExample) |
| KR (1) | KR100834232B1 (enExample) |
| CN (1) | CN101090735A (enExample) |
| AR (2) | AR047469A1 (enExample) |
| AU (1) | AU2005216709B2 (enExample) |
| BR (1) | BRPI0506496B8 (enExample) |
| CA (1) | CA2554346C (enExample) |
| CO (1) | CO5700794A2 (enExample) |
| CY (1) | CY1119188T1 (enExample) |
| DK (1) | DK1713504T3 (enExample) |
| ES (1) | ES2638113T3 (enExample) |
| HU (1) | HUE034099T2 (enExample) |
| IL (1) | IL176676A0 (enExample) |
| LT (1) | LT1713504T (enExample) |
| NO (1) | NO20063858L (enExample) |
| NZ (1) | NZ548236A (enExample) |
| PL (1) | PL1713504T3 (enExample) |
| PT (1) | PT1713504T (enExample) |
| RU (1) | RU2332997C2 (enExample) |
| SI (1) | SI1713504T1 (enExample) |
| TW (1) | TW200524632A (enExample) |
| WO (1) | WO2005082416A2 (enExample) |
| ZA (1) | ZA200605148B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013273764B2 (en) * | 2011-11-29 | 2016-05-05 | Zoetis Services Llc | Pharmaceutical compositions |
| SG11201401597TA (en) * | 2011-11-29 | 2014-05-29 | Jurox Pty Ltd | Methods of preserving injectable pharmaceutical compositions comprising a cyclodextrin and a hydrophobic drug |
| DK3021832T3 (da) * | 2013-07-19 | 2021-05-25 | Boehringer Ingelheim Vetmedica Gmbh | Konserverede etherificerede cyclodextrinderivater indeholdende flydende vandig farmaceutisk sammensætning |
| ES2593210T3 (es) | 2013-12-04 | 2016-12-07 | Boehringer Ingelheim Vetmedica Gmbh | Composiciones farmacéuticas mejoradas de pimobendán |
| NL2015865B1 (en) | 2015-11-27 | 2017-06-13 | Le Vet B V | Maropitant Formulation. |
| IL312486B2 (en) | 2017-04-10 | 2025-05-01 | Chase Therapeutics Corp | NK1 antagonist combination and method for treating synucleinopathies |
| KR20250069704A (ko) | 2017-06-30 | 2025-05-19 | 체이스 테라퓨틱스 코포레이션 | 우울증을 치료하기 위한 nk-1 길항제 조성물 및 우울증 치료에 사용하는 방법 |
| JP7455852B2 (ja) * | 2019-02-15 | 2024-03-26 | ソール インターナショナル ディベロップメント エルティーディー． | 注射可能なフェノール製剤およびその使用の方法 |
| EP3725298A1 (en) | 2019-04-16 | 2020-10-21 | Faes Farma, S.A. | Stable and preserved pharmaceutical compositions of bilastine |
| CN112370451A (zh) * | 2020-12-08 | 2021-02-19 | 河北科技大学 | 一种枸橼酸马罗匹坦包合物、注射液及制备方法 |
| AT527172A1 (de) | 2023-04-25 | 2024-11-15 | Vetviva Richter Gmbh | Maropitantformulierung |
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| RU2103269C1 (ru) | 1991-05-31 | 1998-01-27 | Пфайзер Инк. | Производные хинуклидина или их фармацевтически приемлемые соли и фармацевтическая композиция |
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| DE10228049A1 (de) | 2002-06-24 | 2004-01-15 | Merck Patent Gmbh | Flüssige Zubereitung enthaltend Oligopeptide |
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2005
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- 2005-01-17 LT LTEP05702263.4T patent/LT1713504T/lt unknown
- 2005-01-17 CA CA002554346A patent/CA2554346C/en not_active Expired - Lifetime
- 2005-01-17 EP EP05702263.4A patent/EP1713504B1/en not_active Expired - Lifetime
- 2005-01-17 NZ NZ548236A patent/NZ548236A/en not_active IP Right Cessation
- 2005-01-17 KR KR1020067015283A patent/KR100834232B1/ko not_active Expired - Lifetime
- 2005-01-17 WO PCT/IB2005/000100 patent/WO2005082416A2/en not_active Ceased
- 2005-01-17 PL PL05702263T patent/PL1713504T3/pl unknown
- 2005-01-17 AU AU2005216709A patent/AU2005216709B2/en not_active Expired
- 2005-01-17 US US10/588,070 patent/US8183230B2/en active Active
- 2005-01-17 HU HUE05702263A patent/HUE034099T2/en unknown
- 2005-01-17 ES ES05702263.4T patent/ES2638113T3/es not_active Expired - Lifetime
- 2005-01-17 BR BRPI0506496A patent/BRPI0506496B8/pt active IP Right Grant
- 2005-01-17 SI SI200532166T patent/SI1713504T1/sl unknown
- 2005-01-17 CN CNA2005800032849A patent/CN101090735A/zh active Pending
- 2005-01-17 RU RU2006127422/15A patent/RU2332997C2/ru not_active IP Right Cessation
- 2005-01-17 DK DK05702263.4T patent/DK1713504T3/en active
- 2005-01-17 JP JP2006550330A patent/JP5021318B2/ja not_active Expired - Lifetime
- 2005-01-27 AR ARP050100283A patent/AR047469A1/es not_active Application Discontinuation
- 2005-01-28 TW TW094102680A patent/TW200524632A/zh unknown
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2006
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- 2006-07-03 IL IL176676A patent/IL176676A0/en unknown
- 2006-07-26 CO CO06073023A patent/CO5700794A2/es not_active Application Discontinuation
- 2006-08-29 NO NO20063858A patent/NO20063858L/no not_active Application Discontinuation
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2017
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- 2017-08-16 AR ARP170102291A patent/AR109357A2/es not_active Application Discontinuation
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