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| {{Drugbox
| | #REDIRECT [[Cefoperazone]] |
| | Watchedfields = changed
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| | verifiedrevid = 443509478
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| | IUPAC_name = (6''R'',7''R'')-7-[(2''R'')-2-{[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1''H''-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
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| | image = Cefoperazone.png
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| | image2 = Cefoperazone_ball-and-stick.png
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| <!--Clinical data-->
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| | tradename =
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| | Drugs.com = {{drugs.com|CONS|cefoperazone}}
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| | MedlinePlus = a601206
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| | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| | pregnancy_US = <!-- A / B / C / D / X -->
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| | pregnancy_category =
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| | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
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| | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
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| | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
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| | legal_status =
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| | routes_of_administration =
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| | |
| <!--Pharmacokinetic data-->
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| | bioavailability =
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| | protein_bound =
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| | metabolism =
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| | elimination_half-life =
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| | excretion = Hepatic
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| | |
| <!--Identifiers-->
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| | CASNo_Ref = {{cascite|correct|CAS}}
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| | CAS_number_Ref = {{cascite|correct|??}}
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| | CAS_number = 62893-19-0
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| | ATC_prefix = J01
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| | ATC_suffix = DD12
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| | ATC_supplemental = {{ATCvet|J51|DD12}}
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| | PubChem = 44185
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| | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| | DrugBank = DB01329
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| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| | ChemSpiderID = 40206
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| | UNII_Ref = {{fdacite|correct|FDA}}
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| | UNII = 7U75I1278D
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| | KEGG_Ref = {{keggcite|correct|kegg}}
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| | KEGG = D07645
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| | ChEMBL_Ref = {{ebicite|correct|EBI}}
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| | ChEMBL = 507674
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| | |
| <!--Chemical data-->
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| | C=25 | H=27 | N=9 | O=8 | S=2
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| | molecular_weight = 645.67 g/mol
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| | smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccc(O)cc3)NC(=O)N4C(=O)C(=O)N(CC)CC4)CSc5nnnn5C)C(=O)O
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| | 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
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| | InChIKey = GCFBRXLSHGKWDP-XCGNWRKABH
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| | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| | 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
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| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChIKey = GCFBRXLSHGKWDP-XCGNWRKASA-N
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| }}
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| __NOTOC__
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| {{SI}}
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| {{CMG}}
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| ==Overview==
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| '''Cefoperazone''' is a third-generation [[cephalosporin]] [[antibiotic]], marketed by [[Pfizer]] under the name '''Cefobid''', and also marked by Pharco B International under the name Cefazone and also marketed by Sigmatec Pharmaceuticals under the name Cefoperazone. It is one of few cephalosporin antibiotics effective in treating ''[[Pseudomonas]]'' bacterial infections which are otherwise resistant to these antibiotics.
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| Cefina-SB is a combination of [[sulbactam]] and cefoperazone. Cefoperazone exerts its bactericidal effect by inhibiting the [[bacterial]] [[cell wall]] 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. [http://www.gepach.com Gepach International] markets this combination of cefoperazone with sulbactam under the brand name Bacperazone.In India and SriLanka (Cefoperazone-Sulbactam) is manufacterd by [[Pfizer]] under the brand name of Magnex/Magnex-Forte depending on the Cefoperazone-Sulbactam ratio.
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| ==Spectrum of bacterial susceptibility==
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| 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.
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| * ''Haemophilus influenzae'': 0.12 - 0.25 µg/ml
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| * ''Staphylococcus aureus'': 0.125 - 32 µg/ml
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| * ''Streptococcus pneumoniae'': ≤0.007 - 1 µg/ml
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| <ref>http://antibiotics.toku-e.com/antimicrobial_462_1.html</ref> <ref>http://www.toku-e.com/Assets/MIC/Cefoperazone%20sodium.pdf</ref>
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| ==Adverse effects==
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| Cefoperazone contains an ''N''-methylthiotetrazole (NMTT or 1-MTT) [[side chain]]. As the antibiotic is broken down in the body, it releases free NMTT, which can cause [[hypoprothrombinemia]] (likely due to [[enzyme inhibitor|inhibition]] of the [[enzyme]] [[vitamin K epoxide reductase]]) and a reaction with ethanol similar to that produced by [[disulfiram]] (Antabuse), due to inhibition of [[aldehyde dehydrogenase]].<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> | |
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| ==References==
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| {{Reflist|2}}
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| {{-}}
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| {{CephalosporinAntiBiotics}}
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| [[Category:Cephalosporin antibiotics]]
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| [[Category:Tetrazoles]]
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| [[Category:Piperazines]]
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| [[Category:Phenols]]
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| [[Category:Drug]]
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| [[Category:Lactams]]
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