CA1314231C - Ifosphamide lyophilisate and process for its preparation - Google Patents
Ifosphamide lyophilisate and process for its preparationInfo
- Publication number
- CA1314231C CA1314231C CA000550706A CA550706A CA1314231C CA 1314231 C CA1314231 C CA 1314231C CA 000550706 A CA000550706 A CA 000550706A CA 550706 A CA550706 A CA 550706A CA 1314231 C CA1314231 C CA 1314231C
- Authority
- CA
- Canada
- Prior art keywords
- ifosfamide
- weight
- hexitol
- process according
- solution
- 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
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 229960001101 ifosfamide Drugs 0.000 title claims abstract description 84
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 17
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000243 solution Substances 0.000 claims description 51
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 235000010355 mannitol Nutrition 0.000 claims description 16
- 229930195725 Mannitol Natural products 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 239000000594 mannitol Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 230000008014 freezing Effects 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 238000011049 filling Methods 0.000 description 24
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- 238000004108 freeze drying Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000001035 drying Methods 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229960002920 sorbitol Drugs 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 238000001802 infusion Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000011146 sterile filtration Methods 0.000 description 3
- ZZVDXRCAGGQFAK-UHFFFAOYSA-N 2h-oxazaphosphinine Chemical class N1OC=CC=P1 ZZVDXRCAGGQFAK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-UNTFVMJOSA-N L-iditol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO FBPFZTCFMRRESA-UNTFVMJOSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- FBPFZTCFMRRESA-FBXFSONDSA-N Allitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-FBXFSONDSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-altritol Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- FBPFZTCFMRRESA-OMMKOOBNSA-N L-altritol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@@H](O)CO FBPFZTCFMRRESA-OMMKOOBNSA-N 0.000 description 1
- FBPFZTCFMRRESA-BXKVDMCESA-N L-mannitol Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO FBPFZTCFMRRESA-BXKVDMCESA-N 0.000 description 1
- 229930182842 L-mannitol Natural products 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- -1 for example mannitol Chemical compound 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FGCSIJPPCNCQJB-FAOVPRGRSA-M sodium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;chloride Chemical compound [Na+].[Cl-].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O FGCSIJPPCNCQJB-FAOVPRGRSA-M 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
-
- 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
-
- 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
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Amplifiers (AREA)
- Control Of El Displays (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Indole Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3637089.4 | 1986-10-31 | ||
| DE3637089 | 1986-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1314231C true CA1314231C (en) | 1993-03-09 |
Family
ID=6312873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000550706A Expired - Lifetime CA1314231C (en) | 1986-10-31 | 1987-10-30 | Ifosphamide lyophilisate and process for its preparation |
Country Status (25)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE65402T1 (de) * | 1988-03-19 | 1991-08-15 | Asta Pharma Ag | Ifosfamid-mesna-lyophilisat und verfahren zu dessen herstellung. |
| US5227373A (en) * | 1991-10-23 | 1993-07-13 | Bristol-Myers Squibb Co. | Lyophilized ifosfamide compositions |
| WO1995007083A1 (en) * | 1993-09-10 | 1995-03-16 | F.H. Faulding & Co. Limited | Ifosfamide lyophilisate composition |
| DE19529057B4 (de) * | 1995-08-08 | 2007-12-13 | Baxter Healthcare S.A. | Ifosfamid-Lyophilisat-Zubereitungen |
| KR20010034552A (ko) * | 1998-03-03 | 2001-04-25 | 요시히코 시오노 | 포스포리파제 저해제인 소듐[[3-(2-아미노-1,2-디옥소에틸)-2-에틸-1-(페닐메틸)-1ｈ-인돌-4-일]옥시]아세테이트를 포함하는 약학적 조성물 |
| BR0314068A (pt) * | 2002-09-05 | 2005-07-05 | Bharat Serums & Vaccines Ltd | Processo para a preparação de uma composição estável com baixo nìvel de toxicidade; composição estável que contém oxazafosforina; uso de uma composição estável que contém oxazafosforina; e método de tratamento de uma doença maligna |
| MXPA05005919A (es) * | 2002-12-02 | 2005-09-21 | Bharat Serums & Vaccines Ltd | Composiciones de ifosfamida para la administracion parenteral, y un proceso para su preparacion. |
| US8436190B2 (en) * | 2005-01-14 | 2013-05-07 | Cephalon, Inc. | Bendamustine pharmaceutical compositions |
| BRPI0715279A2 (pt) * | 2006-09-29 | 2013-06-11 | Infa Sa | sistema de embalagem, sistema de embalagem para uma composiÇço farmacÊutica, mÉtodo para transferir uma composiÇço farmcÊutica para administraÇço por infusço intravenosa, uso de um sistema de embalagem, kit para administraÇço parenteral de fÁrmacos com um acesso intravenoso e kit admnistraÇço parenteral de princÍpios ativos |
| CN105900385B (zh) * | 2014-12-04 | 2019-08-27 | 华为技术有限公司 | 在数据通信网中的负载分配 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732340A (en) * | 1966-07-11 | 1973-05-08 | Asta Werke Ag Chem Fab | N',o-propylene phosphoric acid ester diamides |
| DE2750207A1 (de) * | 1977-05-09 | 1978-11-16 | Walton J Smith | Gefriergetrocknete zusammensetzungen, insbesondere gefriergetrocknete pharmazeutische praeparate und verfahren zu deren herstellung |
| DE3279834D1 (en) * | 1981-12-31 | 1989-08-31 | Asta Pharma Ag | 4-sulfido-oxaza phosphorines and their use in the treatment of cancer, and in immunosuppression |
| US4537883A (en) * | 1982-11-12 | 1985-08-27 | Mead Johnson & Company | Lyophilized cyclophosphamide |
-
1987
- 1987-09-15 NO NO873860A patent/NO873860L/no unknown
- 1987-10-20 ES ES87115322T patent/ES2017982B3/es not_active Expired - Lifetime
- 1987-10-20 DE DE8787115322T patent/DE3764235D1/de not_active Expired - Lifetime
- 1987-10-20 EP EP87115322A patent/EP0265812B1/de not_active Expired - Lifetime
- 1987-10-20 AT AT87115322T patent/ATE55250T1/de not_active IP Right Cessation
- 1987-10-23 MX MX895887A patent/MX8958A/es unknown
- 1987-10-26 IN IN837/CAL/87A patent/IN168119B/en unknown
- 1987-10-27 FI FI874727A patent/FI87140C/fi not_active IP Right Cessation
- 1987-10-28 EG EG61687A patent/EG18333A/xx active
- 1987-10-29 JP JP62272002A patent/JPS63159319A/ja active Granted
- 1987-10-29 RU SU874203570A patent/RU1836079C/ru active
- 1987-10-29 IL IL84312A patent/IL84312A/xx not_active IP Right Cessation
- 1987-10-29 PT PT86032A patent/PT86032B/pt unknown
- 1987-10-29 UA UA4203570A patent/UA11075A/uk unknown
- 1987-10-30 DK DK569687A patent/DK169308B1/da not_active IP Right Cessation
- 1987-10-30 ZA ZA878183A patent/ZA878183B/xx unknown
- 1987-10-30 AU AU80529/87A patent/AU598602B2/en not_active Ceased
- 1987-10-30 YU YU01973/87A patent/YU197387A/xx unknown
- 1987-10-30 CA CA000550706A patent/CA1314231C/en not_active Expired - Lifetime
- 1987-10-30 DD DD87308471A patent/DD262582A5/de not_active IP Right Cessation
- 1987-10-30 KR KR1019870012077A patent/KR900003491B1/ko not_active Expired
- 1987-10-30 HU HU874900A patent/HU197987B/hu unknown
-
1990
- 1990-08-09 GR GR90400533T patent/GR3000708T3/el unknown
-
1992
- 1992-10-27 LV LVP-92-174A patent/LV10051B/lv unknown
-
1993
- 1993-07-07 GE GEAP1993972A patent/GEP19971025B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |