CA1068680A - Method of preparing stable sterile crystalline cephalosporins for parenteral administration - Google Patents
Method of preparing stable sterile crystalline cephalosporins for parenteral administrationInfo
- Publication number
- CA1068680A CA1068680A CA246,175A CA246175A CA1068680A CA 1068680 A CA1068680 A CA 1068680A CA 246175 A CA246175 A CA 246175A CA 1068680 A CA1068680 A CA 1068680A
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- cephalosporin
- temperature
- hours
- percent
- 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
Links
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 58
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 57
- 150000001780 cephalosporins Chemical class 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000007911 parenteral administration Methods 0.000 title claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract description 15
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims abstract description 15
- 229960003237 betaine Drugs 0.000 claims abstract description 15
- 229960000603 cefalotin Drugs 0.000 claims abstract description 15
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 claims abstract description 15
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 claims abstract description 15
- 229960003408 cefazolin sodium Drugs 0.000 claims abstract description 15
- 229960003866 cefaloridine Drugs 0.000 claims abstract description 14
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 claims abstract description 14
- 230000006911 nucleation Effects 0.000 claims abstract description 14
- 238000010899 nucleation Methods 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 42
- 239000013078 crystal Substances 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 25
- 239000003708 ampul Substances 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 230000001954 sterilising effect Effects 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 abstract description 19
- 238000003860 storage Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 description 9
- 238000011049 filling Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008227 sterile water for injection Substances 0.000 description 2
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000004686 pentahydrates Chemical class 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000004383 yellowing Methods 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
- A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—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 sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/567,224 US4029655A (en) | 1975-04-11 | 1975-04-11 | Method of preparing stable sterile crystalline cephalosporins for parenteral administration |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068680A true CA1068680A (en) | 1979-12-25 |
Family
ID=24266257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA246,175A Expired CA1068680A (en) | 1975-04-11 | 1976-02-20 | Method of preparing stable sterile crystalline cephalosporins for parenteral administration |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4029655A (enExample) |
| JP (1) | JPS51123813A (enExample) |
| BE (1) | BE840280A (enExample) |
| CA (1) | CA1068680A (enExample) |
| DE (1) | DE2614668C2 (enExample) |
| ES (1) | ES446906A1 (enExample) |
| FR (1) | FR2306993A1 (enExample) |
| GB (1) | GB1537874A (enExample) |
| IE (1) | IE42955B1 (enExample) |
| IL (1) | IL49073A (enExample) |
| NL (1) | NL7603659A (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996355A (en) * | 1975-01-02 | 1976-12-07 | American Home Products Corporation | Permanent suspension pharmaceutical dosage form |
| IL53427A0 (en) * | 1976-11-24 | 1978-01-31 | Lilly Co Eli | Method of preparing a rapidly dissolving powder of sterile crystalline cefozolin sodium for parenteral administration |
| US4115644A (en) * | 1977-09-19 | 1978-09-19 | Eli Lilly And Company | Process for preparing pure cefamandole from alkali metal and ammonium salts thereof |
| US4132848A (en) * | 1977-11-03 | 1979-01-02 | Eli Lilly And Company | Method of preparing a rapidly dissolving powder of crystalline cephalothin sodium for parenteral administration |
| FR2421905A1 (fr) * | 1977-11-24 | 1979-11-02 | Lilly Co Eli | Preparation d'une poudre de cephalothine-sodiu m stable, pour administration parenterale |
| JPS54147917A (en) * | 1978-05-08 | 1979-11-19 | Sumitomo Chem Co Ltd | Ferrze-drying method |
| YU44680B (en) * | 1982-07-30 | 1990-12-31 | Glaxo Lab Ltd | Process for obtaining very pure amorphous form of cephuroxim axetile |
| JPS60120886A (ja) * | 1983-12-02 | 1985-06-28 | Takeda Chem Ind Ltd | セフェムカルボン酸のナトリウム塩の結晶 |
| JPH06786B2 (ja) * | 1984-02-22 | 1994-01-05 | 塩野義製薬株式会社 | セフアロチンナトリウムの結晶性凍結乾燥製剤の製造法 |
| US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
| US5244891A (en) * | 1985-08-05 | 1993-09-14 | Bristol-Myers Squibb Company | Injectable compositions of cefepime dihydrochloride hydrate |
| US4714760A (en) * | 1985-08-20 | 1987-12-22 | Bristol-Myers Company | Cephalosporin intermediates |
| US4808617A (en) * | 1985-12-18 | 1989-02-28 | Bristol-Myers Company | Lyophilized or precipitated cephalosporin zwitterion and salt combination |
| GB8808433D0 (en) * | 1988-04-11 | 1988-05-11 | Merck Sharp & Dohme | Therapeutic agents |
| TW264475B (enExample) * | 1991-09-20 | 1995-12-01 | Takeda Pharm Industry Co Ltd | |
| US6111098A (en) * | 1994-05-02 | 2000-08-29 | Shionogi & Co., Ltd. | Crystal of pyrrolidylthiocarbapenem derivative, lyophilized preparation containing said crystal, and process for producing the same |
| DE602005002742T2 (de) * | 2004-04-22 | 2008-01-24 | Pfizer Products Inc., Groton | Verfahren zur stabilisierung von ungeordnetem cefovecin-natriumsalz |
| CN101759708B (zh) * | 2008-12-23 | 2012-07-04 | 深圳信立泰药业股份有限公司 | 头孢地嗪钠晶型及其制备方法和含有该晶型的药物组合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3085884A (en) * | 1958-07-28 | 1963-04-16 | Liquefreeze Company Inc | Method of freezing and shipping foodstuffs |
| GB1234802A (en) * | 1968-04-19 | 1971-06-09 | British American Tobacco Co | Improvements relating to the packing of liquids |
| US3725003A (en) * | 1969-11-04 | 1973-04-03 | Moore Perk Corp | Method of sterile packaging |
-
1975
- 1975-04-11 US US05/567,224 patent/US4029655A/en not_active Expired - Lifetime
-
1976
- 1976-02-18 IE IE316/76A patent/IE42955B1/en unknown
- 1976-02-19 IL IL49073A patent/IL49073A/xx unknown
- 1976-02-20 CA CA246,175A patent/CA1068680A/en not_active Expired
- 1976-03-31 FR FR7609360A patent/FR2306993A1/fr active Granted
- 1976-04-01 JP JP51036674A patent/JPS51123813A/ja active Granted
- 1976-04-01 BE BE1007297A patent/BE840280A/xx not_active IP Right Cessation
- 1976-04-05 DE DE2614668A patent/DE2614668C2/de not_active Expired
- 1976-04-07 NL NL7603659A patent/NL7603659A/xx not_active Application Discontinuation
- 1976-04-07 GB GB14019/76A patent/GB1537874A/en not_active Expired
- 1976-04-10 ES ES446906A patent/ES446906A1/es not_active Expired
-
1977
- 1977-02-09 US US05/767,234 patent/US4104391A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IL49073A (en) | 1979-03-12 |
| BE840280A (fr) | 1976-10-01 |
| DE2614668C2 (de) | 1986-10-30 |
| DE2614668A1 (de) | 1976-10-21 |
| US4104391A (en) | 1978-08-01 |
| IL49073A0 (en) | 1976-04-30 |
| JPS6143356B2 (enExample) | 1986-09-26 |
| NL7603659A (nl) | 1976-10-13 |
| JPS51123813A (en) | 1976-10-28 |
| FR2306993B1 (enExample) | 1978-11-17 |
| GB1537874A (en) | 1979-01-04 |
| IE42955L (en) | 1976-10-11 |
| FR2306993A1 (fr) | 1976-11-05 |
| US4029655A (en) | 1977-06-14 |
| ES446906A1 (es) | 1977-05-16 |
| IE42955B1 (en) | 1980-11-19 |
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