{{short description|Antibiotic}} {{Drugbox | Watchedfields = changed | verifiedrevid = 443509478 | 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 | image = Cefoperazone.svg | image_class = skin-invert-image | image2 = Cefoperazone ball-and-stick.png | image_class2 = bg-transparent <!--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 = 40206 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7U75I1278D | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D07645 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 507674 <!--Chemical data--> | C=25 | H=27 | N=9 | O=8 | S=2 | 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 | 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = GCFBRXLSHGKWDP-XCGNWRKASA-N }} <!-- Definition and medical uses --> '''Cefoperazone''' is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name '''Cefobid'''. It is one of few cephalosporin antibiotics effective in treating ''Pseudomonas'' bacterial infections which are otherwise resistant to these antibiotics.
<!-- Society and culture --> 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> Cefoperazone/sulbactam (Sulperazon) is a co-formulation with sulbactam.
==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 μg/ml * ''Staphylococcus aureus'': 0.125 - 32 μg/ml * ''Streptococcus pneumoniae'': ≤0.007 - 1 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== 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 inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse effect), due to inhibition of aldehyde dehydrogenase.<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>
== References == {{Reflist}}
{{CephalosporinAntiBiotics}}
Category:Acetaldehyde dehydrogenase inhibitors Category:Cephalosporin antibiotics Category:Tetrazoles Category:Diketopiperazines Category:4-Hydroxyphenyl compounds Category:Acetamides Category:Lactams Category:Drugs developed by Pfizer