U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N4CCN(CC)C(=O)C4=O)C5=CC=C(O)C=C5)C(O)=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 No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/cefobid-drug.htm

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEFOBID

Approved Use

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.

Launch Date

1982
Curative
CEFOBID

Approved Use

Peritonitis and Other Intra-abdominal Infections caused by E. coli, P. aeruginosa,* and anaerobic gram-negative bacilli (including Bacteroides fragilis).

Launch Date

1982
Curative
CEFOBID

Approved Use

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.

Launch Date

1982
Curative
CEFOBID

Approved Use

Infections of the Skin and Skin Structures caused by S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes,* and P. aeruginosa.

Launch Date

1982
Curative
CEFOBID

Approved Use

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.

Launch Date

1982
Curative
CEFOBID

Approved Use

Urinary Tract Infections caused by Escherichia coli and Pseudomonas aeruginosa.

Launch Date

1982
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
154.9 mg/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
221.8 mg/mL
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
211.62 mg × h/L per 1.73 m²
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
421.63 mg × h/L per 1.73 m²
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1147.5 mg × h/L
100 mg/kg 3 times / day multiple, intravenous
dose: 100 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
541.2 mg × h/L
50 mg/kg 3 times / day multiple, intravenous
dose: 50 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
761.7 mg × h/L
100 mg/kg single, intravenous
dose: 100 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.649 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.044 h
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.063 h
100 mg/kg 3 times / day multiple, intravenous
dose: 100 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
0.185 h
50 mg/kg 3 times / day multiple, intravenous
dose: 50 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
0.063 h
100 mg/kg single, intravenous
dose: 100 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFOPERAZONE serum
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1330 uM]
yes [Ki 1890 uM]
yes [Ki 210 uM]
yes [Ki 2800 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
[Cefoperazone (Medocef*) in the modern therapy of severe bacterial infections].
2001
Biodegradable polyhydroxyalkanoate implants for osteomyelitis therapy: in vitro antibiotic release.
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
A novel plasmid-mediated beta-lactamase that hydrolyzes broad-spectrum cephalosporins in a clinical isolate of Klebsiella pneumoniae.
2001 Dec
Development of a new protocol for the isolation and quantification of Arcobacter species from poultry products.
2001 Dec 30
[Antimicrobial susceptibility of Pseudomonas aeruginosa isolated in Fukushima Prefecture].
2001 Feb
In vivo application of biodegradable controlled antibiotic release systems for the treatment of implant-related osteomyelitis.
2001 Jan
[Determination of unbound concentration of drug in drug-human serum albumin mixture by high performance frontal analysis].
2001 Jul
Randomized, double-blind, controlled study of cefoperazone-sulbactam plus cotrimoxazole versus ceftazidime plus cotrimoxazole for the treatment of severe melioidosis.
2001 Jul 1
[Characterization of cefoperazone resistance gene on plasmid pFC in E. coli HX88108].
2001 Mar
Cephalosporins in surgical prophylaxis.
2001 Nov
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.
2001 Oct
[Complex detoxication therapy in obstructive jaundice of tumor genesis].
2002
Serotypes, virulence factors, antibiotic sensitivity, beta-lactamase activity and plasmid analysis of Salmonella from children with diarrhea in Tripoli (Libya).
2002
The importance of pets as reservoirs of resistant Enterococcus strains, with special reference to vancomycin.
2002 Aug
Klebsiella pneumoniae: epidemiology and analysis of risk factors for infections caused by resistant strains.
2002 Aug
[Molecular characteristics of beta-lactamase from Klebsiella pneumoniae].
2002 Feb 25
Pharmacokinetics of cefoperazone and sulbactam in liver transplant patients.
2002 Jun
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
The role of cefoperazone-sulbactam for treatment of severe melioidosis.
2002 Mar 1
In vitro antibiotic release from poly(3-hydroxybutyrate-co-3-hydroxyvalerate) rods.
2002 Mar-Apr
In vitro antimicrobial susceptibility of 183 Pseudomonas aeruginosa strains isolated from dogs to selected antipseudomonal agents.
2002 May
In vitro susceptibility of four serotypes of enterohaemorrhagic Escherichia coli to antimicrobial agents.
2002 May
Comparison of screening methods for TEM- and SHV-derived extended-spectrum beta-lactamase detection.
2002 Nov
Pseudomonas aeruginosa: resistance and therapy.
2002 Sep
The status of drug resistance and ampC gene expression in Enterobacter cloacae.
2003 Aug
[Comparative analysis of the effectiveness and costs of azithromycin and cefoperazone treatment of patients during COPD exacerbation].
2003 Jan
[Changes of antimicrobial resistance among nonfermenting gram-negative bacilli isolated from intensive care units from 1994 to 2001 in China].
2003 Mar 10
Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics.
2003 Mar 28
[Assay of Acinetobacter SPP drug-resistance by Kirby-Bauer and Etest method].
2003 May
Double-disk synergy test positivity in Stenotrophomonas maltophilia clinical strains.
2004
[Changes in plasma levels of LPS, TNFalpha and IL-6 in burn patients with severe infection treated with Imipenem or Cefoperazone].
2004 Apr
Pacemaker lead endocarditis caused by Achromobacter xylosoxidans.
2004 Apr
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
[Survey of the utilization and adverse effects of antibacterial drugs in patients admitted for respiratory diseases].
2005 Feb
Patents

Sample Use Guides

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: Other
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 Fri Dec 15 16:34:23 GMT 2023
Edited
by admin
on Fri Dec 15 16:34:23 GMT 2023
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 [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
Cefoperazone [WHO-DD]
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 Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
WHO-VATC QJ01DD62
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
WHO-ATC J01DD62
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
LIVERTOX NBK547862
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
LIVERTOX NBK548666
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
WHO-VATC QJ51DD12
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NCI_THESAURUS C357
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
WHO-ATC J01DD12
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
WHO-VATC QJ01DD12
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000175488
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
NDF-RT N0000011161
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
Code System Code Type Description
FDA UNII
7U75I1278D
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
ECHA (EC/EINECS)
263-749-4
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
CHEBI
3493
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
DRUG CENTRAL
543
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
PUBCHEM
44187
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
EVMPD
SUB07402MIG
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
WIKIPEDIA
CEFOPERAZONE
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL507674
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
NCI_THESAURUS
C61663
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
MERCK INDEX
m3201
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY Merck Index
CAS
62893-19-0
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
SMS_ID
100000081804
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
LACTMED
Cefoperazone
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
MESH
D002438
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
RXCUI
2184
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID2022759
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
DRUG BANK
DB01329
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
INN
4742
Created by admin on Fri Dec 15 16:34:23 GMT 2023 , Edited by admin on Fri Dec 15 16:34:23 GMT 2023
PRIMARY
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