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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H27N9O8S2
Molecular Weight 645.667
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFOPERAZONE

SMILES

CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SCC(CSC4=NN=NN4C)=C(N3C2=O)C(O)=O)C5=CC=C(O)C=C5)C(=O)C1=O

InChI

InChIKey=GCFBRXLSHGKWDP-XCGNWRKASA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C25H27N9O8S2
Molecular Weight 645.667
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cefoperazone (marketed under the name Cefobid) is a third-generation cephalosporin antibiotic. Cefoperazone has a broad spectrum of activity: Respiratory Tract Infections caused by S. pneumoniae, H. influenzae, S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes (Group A beta-hemolytic streptococci), P. aeruginosa, Klebsiella pneumoniae, E. coli, Proteus mirabilis, and Enterobacter species. Peritonitis and Other Intra-abdominal Infections caused by E. coli, P. aeruginosa, and anaerobic gram-negative bacilli (including Bacteroides fragilis). Bacterial Septicemia caused by S. pneumoniae, S. agalactiae, S. aureus, Pseudomonas aeruginosa, E. coli, Klebsiella spp., Klebsiella pneumoniae, Proteus species (indole-positive and indole-negative), Clostridium spp. and anaerobic gram-positive cocci. Infections of the Skin and Skin Structures caused by S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes, and P. aeruginosa. Pelvic Inflammatory Disease, Endometritis, and Other Infections of the Female Genital Tract caused by N. gonorrhoeae, S. epidermidis, S. agalactiae, E. coli, Clostridium spp., Bacteroides species (including Bacteroides fragilis), and anaerobic gram-positive cocci. Cefobid has no activity against Chlamydia trachomatis. Therefore, when Cefobid is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added. Urinary Tract Infections caused by Escherichia coli and Pseudomonas aeruginosa. Cefoperazone, a third-generation cephalosporin, interferes with cell wall synthesis by binding to the penicillin-binding proteins (PBPs), thus preventing cross-linking of nascent peptidoglycan. Cefoperazone is stable to penicillinases and has a high degree of stability to many beta-lactamases produced by gram-negative bacteria. When tested in vitro, cefoperazone has demonstrated synergistic interactions with aminoglycosides against gram-negative bacilli. As with all cephalosporins, hypersensitivity manifested by skin reactions or drug fever. Reversible neutropenia may occur with prolonged administration. Diarrhea or loose stools has been reported also.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Cefoperazone (Medocef*) in the modern therapy of severe bacterial infections].
2001
Effect of cefaperazone/sulbactam and ampicillin/sulbactam on the in vitro activity of human erythrocyte glucose-6-phosphate dehydrogenase.
2001
[The clinical investigation of bacteriology of chronic suppurative otitis media].
2001 Dec
Antibiotic combinations in polymicrobic diabetic foot infections.
2001 Dec
Survey of antibiotic resistance in Pseudomonas aeruginosa by The Tokyo Johoku Association of Pseudomonas Studies.
2001 Dec
Nosocomial bloodstream infection in pediatric patients: Siriraj Hospital, Bangkok; 1996-1999.
2001 Feb
[Determination of unbound concentration of drug in drug-human serum albumin mixture by high performance frontal analysis].
2001 Jul
[Clinical analysis of neutropenic fever associated with hematological disorders].
2001 Mar
Seroprevalence and antibiotic sensitivity of serotypes of Salmonella enterica in Greek pig herds.
2001 Mar 31
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone.
2002
[A control study on bacterial resistance and clinical features of lower respiratory tract infection with Pseudomonas aeruginosa in medical intensive care unit and general ward].
2002 Dec
[Molecular characteristics of beta-lactamase from Klebsiella pneumoniae].
2002 Feb 25
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice.
2002 Jul
Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci.
2002 Mar
Multiresistant Acinetobacter infections: a role for sulbactam combinations in overcoming an emerging worldwide problem.
2002 Mar
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.
2002 Mar 8
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002 Mar 8
In vitro antibiotic release from poly(3-hydroxybutyrate-co-3-hydroxyvalerate) rods.
2002 Mar-Apr
[beta-lactamase-producing activity and antimicrobial susceptibility of major pathogenic bacteria isolated from clinical samples. Japan beta-lactamase Research Group].
2002 Sep
[Sulperazone in the treatment of severe infections in patients with cancer].
2003
[Yearly changes in antibacterial activities of cefozopran against various clinical isolates between 1996 and 2001--II. Gram-negative bacteria].
2003 Aug
Carbapenem-resistant Pseudomonas aeruginosa-carrying VIM-2 metallo-beta-lactamase determinants, Croatia.
2003 Aug
The status of drug resistance and ampC gene expression in Enterobacter cloacae.
2003 Aug
[Current data on antibiotic resistance of the most important bovine mastitis pathogens in Switzerland].
2003 Dec
Detection limits of antimicrobials in ewe milk by delvotest photometric measurements.
2003 Feb
[Activity of fourth generation cephalosporins against clinical isolates of Enterobacteriaceae].
2003 Jul-Sep
Emergence of ceftriaxone-resistant Salmonella isolates and rapid spread of plasmid-encoded CMY-2-like cephalosporinase, Taiwan.
2003 Mar
[Clinical and bacteriological substantiation of the use of cefoperazone/sulbactam in complex therapy of patients with pyo-destructive forms of lower respiratory tract infection (LRTI)].
2004
Double-disk synergy test positivity in Stenotrophomonas maltophilia clinical strains.
2004
Effective antibiotic regime for postoperative acute cholangitis in biliary atresia--an evolving scene.
2004 Dec
Isolation and characterisation of Arcobacter butzleri from meat.
2004 Feb 15
Derivatives of phosphate Schiff base transition metal complexes: synthesis, studies and biological activity.
2004 Jan
Comparison in a rat thigh abscess model of imipenem, meropenem and cefoperazone-sulbactam against Acinetobacter baumannii strains in terms of bactericidal efficacy and resistance selection.
2004 Jan 8
[Comparison of efficacy between ceftriaxone and cefoperazone plus sulbactam in peri-operative treatment of acute suppurative cholangitis].
2004 Nov 17
[Survey of the utilization and adverse effects of antibacterial drugs in patients admitted for respiratory diseases].
2005 Feb
[Distribution and drug-resistance of 3 500 gram-negative bacteria in Guangzhou].
2005 Feb
Patents

Sample Use Guides

In Vivo Use Guide
The usual adult daily dose is 2 to 4 grams per day administered in equally divided doses every 12 hours. In severe infections or infections caused by less sensitive organisms, the total daily dose and/or frequency may be increased. Patients have been successfully treated with a total daily dosage of 6–12 grams divided into 2, 3 or 4 administrations ranging from 1.5 to 4 grams per dose. When treating infections caused by Streptococcus pyogenes, therapy should be continued for at least 10 days.
Route of Administration: Intravenous; Intramuscular
In Vitro Use Guide
MIC90 of cefoperazone against S. marcescens, E. cloacae, ESBL-K. pneumoniae and A. baumannii were >128 mg/L.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:50:30 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:30 UTC 2019
Record UNII
7U75I1278D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFOPERAZONE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CEFOPERAZONE [MI]
Common Name English
CEFOPERAZONE [VANDF]
Common Name English
CEFOPERAZONE [WHO-DD]
Common Name English
CEFOPERAZONE [INN]
Common Name English
PERACEF
Brand Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((((4-ETHYL-2,3-DIOXO-1-PIPERAZINYL)CARBONYL)AMINO)(4-HYDROXYPHENYL)ACETYL)AMINO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO, (6R-(6.ALPHA.,7.BETA.(R*)))-
Common Name English
(6R,7R)-7-((R)-2-(4-ETHYL-2,3-DIOXO-1-PIPERAZINECARBOXAMIDO)-2-(P-HYDROXYPHENYL)ACETAMIDO-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Common Name English
Classification Tree Code System Code
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
WHO-VATC QJ01DD62
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
WHO-ATC J01DD62
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
LIVERTOX 165
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
WHO-VATC QJ51DD12
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NCI_THESAURUS C357
Created by admin on Mon Oct 21 19:50:30 UTC 2019 , Edited by admin on Mon Oct 21 19:50:30 UTC 2019
WHO-ATC J01DD12
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
WHO-VATC QJ01DD12
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000175488
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
263-749-4
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
PUBCHEM
44187
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
EVMPD
SUB07402MIG
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
WIKIPEDIA
CEFOPERAZONE
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
ChEMBL
CHEMBL507674
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
LactMed
62893-19-0
Created by admin on Mon Oct 21 19:50:30 UTC 2019 , Edited by admin on Mon Oct 21 19:50:30 UTC 2019
PRIMARY
NCI_THESAURUS
C61663
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
MERCK INDEX
M3201
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY Merck Index
CAS
62893-19-0
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
MESH
D002438
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
RXCUI
2184
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY RxNorm
EPA CompTox
62893-19-0
Created by admin on Mon Oct 21 19:50:30 UTC 2019 , Edited by admin on Mon Oct 21 19:50:30 UTC 2019
PRIMARY
DRUG BANK
DB01329
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
INN
4742
Created by admin on Mon Oct 21 19:50:31 UTC 2019 , Edited by admin on Mon Oct 21 19:50:31 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC