Misplaced Pages

Cefoperazone: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 14:01, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 07:05, 4 November 2024 edit undo2001:16b8:b418:1c00:8926:161d:c5f7:7097 (talk) rvTag: Undo 
(62 intermediate revisions by 47 users not shown)
Line 1: Line 1:
{{short description|Antibiotic}}
{{drugbox
{{Drugbox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 414053848 | verifiedrevid = 443509478
| IUPAC_name = ((6R,7R)-7-amino}-2-(4-hydroxyphenyl)acetamido]-3-{methyl}-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid | IUPAC_name = (6''R'',7''R'')-7-amino}-2-(4-hydroxyphenyl)acetamido]-3-{methyl}-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
| image = Cefoperazone.svg | image = Cefoperazone.svg
| image2 = Cefoperazone ball-and-stick.png
<!--Clinical data-->
| tradename =
| Drugs.com = {{drugs.com|CONS|cefoperazone}}
| MedlinePlus = a601206
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category =
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫ | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫ | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫ | legal_status =
⚫ | routes_of_administration =
<!--Pharmacokinetic data-->
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion = Hepatic
<!--Identifiers-->
⚫ | CAS_number_Ref = {{cascite|correct|??}}
⚫ | CAS_number = 62893-19-0
⚫ | ATC_prefix = J01
⚫ | ATC_suffix = DD12
⚫ | ATC_supplemental = {{ATCvet|J51|DD12}}
⚫ | PubChem = 44185
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank = DB01329
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 40206 | ChemSpiderID = 40206
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7U75I1278D | UNII = 7U75I1278D
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| InChI = 1/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1
⚫ | KEGG = D07645
⚫ | smiles = O=C2N1/C(=C(\CS12NC(=O)(c3ccc(O)cc3)NC(=O)N4C(=O)C(=O)N(CC)CC4)CSc5nnnn5C)C(=O)O
| InChIKey = GCFBRXLSHGKWDP-XCGNWRKABH
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 507674 | ChEMBL = 507674
<!--Chemical data-->
⚫ | C=25 | H=27 | N=9 | O=8 | S=2
⚫ | smiles = O=C2N1/C(=C(\CS12NC(=O)(c3ccc(O)cc3)NC(=O)N4C(=O)C(=O)N(CC)CC4)CSc5nnnn5C)C(=O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1 | StdInChI = 1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GCFBRXLSHGKWDP-XCGNWRKASA-N | StdInChIKey = GCFBRXLSHGKWDP-XCGNWRKASA-N
⚫ | CAS_number = 62893-19-0
⚫ | ATC_prefix = J01
⚫ | ATC_suffix = DD12
⚫ | ATC_supplemental = {{ATCvet|J51|DA32}}
⚫ | PubChem = 44185
⚫ | DrugBank = DB01329
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | KEGG = D07645
⚫ | C=25|H=27|N=9|O=8|S=2
| molecular_weight = 645.67 g/mol
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion = Hepatic
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category=
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫ | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫ | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫ | legal_status =
⚫ | routes_of_administration =
}} }}
<!-- Definition and medical uses -->
'''Cefoperazone''' is a third generation ] ], marketed by ] under the name '''Cefobid''', and also marked by ] under the name of '''Cefazone'''and also marketed by "sigmatec " under the name " cefoperazone" . It is one of few ] antibiotics effective in treating '']'' bacterial infections which are otherwise resistant to these antibiotics. '''Cefoperazone''' is a third-generation ] ], marketed by ] under the name '''Cefobid'''. It is one of few cephalosporin antibiotics effective in treating '']'' bacterial infections which are otherwise resistant to these antibiotics.


<!-- Society and culture -->
''Cefina-SB'' is a combination of ] and cefoperazone. Cefoperazone exerts its bactericidal effect by inhibiting the ] ] synthesis, and sulbactam acts as a beta-lactamase inhibitor, to increase the antibacterial activity of cefoperazone against beta-lactamase producing organisms. In some countries, the combination is sold as ''Sulperazone''. markets this combination of Cefoperazone with Sulbactam under the brand name '''Bacperazone'''
It was patented in 1974 and approved for medical use in 1981.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=494 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA494 |language=en}}</ref> ] (Sulperazon) is a co-formulation with ].

==Spectrum of bacterial susceptibility==
Cefoperazone has a broad spectrum of activity and has been used to target bacteria responsible for causing infections of the respiratory and urinary tract, skin, and the female genital tract. The following represents MIC susceptibility data for a few medically significant microorganisms.
* ''Haemophilus influenzae'': 0.12 - 0.25&nbsp;μg/ml
* ''Staphylococcus aureus'': 0.125 - 32&nbsp;μg/ml
* ''Streptococcus pneumoniae'': ≤0.007 - 1&nbsp;μg/ml<ref>{{cite web|url=http://antibiotics.toku-e.com/antimicrobial_462_1.html|title=Cefoperazone (Cefobid) - The Antimicrobial Index Knowledgebase - TOKU-E|website=antibiotics.toku-e.com}}</ref>


==Adverse effects== ==Adverse effects==
Cefoperazone contains an ''N''-methylthiotetrazole (NMTT or 1-MTT) ]. As the antibiotic is broken down in the body, it releases free NMTT, which can cause ] (likely due to ] of the ] ]) and a reaction with ethanol similar to that produced by ] (Antabuse), due to inhibition of ].<ref name=Goldfrank>{{cite book |author=Stork CM |editor=Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.) |title=Goldfrank's toxicologic emergencies |chapter=Antibiotics, antifungals, and antivirals |chapterurl=http://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847 |publisher=McGraw-Hill |location=New York |year=2006 |pages=847 |isbn=0-07-143763-0 |accessdate=2009-07-03}}</ref> Cefoperazone contains an ''N''-methylthiotetrazole (NMTT or 1-MTT) ]. As the antibiotic is broken down in the body, it releases free NMTT, which can cause ] (likely due to ] of the ] ]) and a reaction with ethanol similar to that produced by ] (]), due to inhibition of ].<ref name=Goldfrank>{{cite book | vauthors = Stork CM |veditors=Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA |title=Goldfrank's toxicologic emergencies |chapter=Antibiotics, antifungals, and antivirals |chapter-url=https://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847 |publisher=McGraw-Hill |location=New York |year=2006 |pages=847 |isbn=0-07-143763-0 |access-date=2009-07-03 }}</ref>

==Mechanism of action==
{{Empty section|date=August 2024}}


==References== ==References==
{{Reflist}} {{Reflist}}

{{-}}
{{CephalosporinAntiBiotics}} {{CephalosporinAntiBiotics}}


]
] ]
] ]
] ]
] ]
] ]
] ]
]

{{antibiotic-stub}}

]
]
]
]