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{{drugbox
{{Drugbox
| IUPAC_name       = (6''R'',7''S'')-7-{[2-[(4-ethyl-2,3-dioxo-piperazine-1-<br>carbonyl)amino]-2-(4-hydroxyphenyl)acetyl}amino]-<br>3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-<br>1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
| Watchedfields = changed
| image             = Cefoperazone.svg
| verifiedrevid = 443509478
| CAS_number        = 62893-19-0
| 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
| ATC_prefix        = J01
| image = Cefoperazone.png
| ATC_suffix        = DD12
| image2 = Cefoperazone_ball-and-stick.png
| ATC_supplemental  = {{ATC|J01|DD62}}
<!--Clinical data-->
| PubChem          = 44185
| tradename =
| DrugBank          =
| Drugs.com = {{drugs.com|CONS|cefoperazone}}
| C=25|H=27|N=9|O=8|S=2
| MedlinePlus = a601206
| molecular_weight  = 645.67 g/mol
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| bioavailability  =
| pregnancy_US = <!-- A / B            / C / D / X -->
| protein_bound    =
| pregnancy_category =   
| metabolism        =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| elimination_half-life =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| excretion        =  
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_status =
| pregnancy_category=   
| routes_of_administration =
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
 
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
<!--Pharmacokinetic data-->
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| bioavailability = 
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| protein_bound = 
| legal_status     =  
| metabolism = 
| routes_of_administration =  
| elimination_half-life = 
| excretion = Hepatic
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| 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
| molecular_weight = 645.67 g/mol
| 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
| 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
| InChIKey = GCFBRXLSHGKWDP-XCGNWRKABH
| 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
}}
}}
{{EH}}
__NOTOC__
{{SI}}
{{SI}}
{{CMG}}


==Overview==
==Overview==
'''Cefoperazone''' is a third generation [[cephalosporin]] [[antibiotic]]. Marketed by [[pfizer]] under the name '''Cefobid'''<sup>'''®'''</sup>.
'''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.
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.
 
==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>http://antibiotics.toku-e.com/antimicrobial_462_1.html</ref><ref>http://www.toku-e.com/Assets/MIC/Cefoperazone%20sodium.pdf</ref>


''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. Cefina-SB is available as injection for the treatment of bacterial infections. In some countries, the combination is sold as ''Sulperazone''. Cefoperazone is available in the United States as Cefobid.
==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 [[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>


{{SIB}}
==References==
{{Reflist|2}}
{{-}}
{{CephalosporinAntiBiotics}}
{{CephalosporinAntiBiotics}}


{{WH}}
[[Category:Cephalosporin antibiotics]]
{{WS}}
[[Category:Tetrazoles]]
[[Category:Piperazines]]
[[Category:Phenols]]
[[Category:Drug]]
[[Category:Lactams]]

Latest revision as of 18:47, 18 August 2015

Cefoperazone
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601206
ATC code
Pharmacokinetic data
ExcretionHepatic
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC25H27N9O8S2
Molar mass645.67 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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. 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. 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.

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[1][2]

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), due to inhibition of aldehyde dehydrogenase.[3]

References

  1. ↑ http://antibiotics.toku-e.com/antimicrobial_462_1.html
  2. ↑ http://www.toku-e.com/Assets/MIC/Cefoperazone%20sodium.pdf
  3. ↑ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
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