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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H26N9O8S2.Na
Molecular Weight 667.649
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFOPERAZONE SODIUM

SMILES

[Na+].[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=NCFTXMQPRQZFMZ-WERGMSTESA-M
InChI=1S/C25H27N9O8S2.Na/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);/q;+1/p-1/t15-,16-,22-;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C25H26N9O8S2
Molecular Weight 644.659
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEFOBID
Curative
CEFOBID
Curative
CEFOBID
Curative
CEFOBID
Curative
CEFOBID
Curative
CEFOBID

Cmax

ValueDoseCo-administeredAnalytePopulation
154.9 mg/mL
1 g single, intravenous
CEFOPERAZONE serum
Homo sapiens
221.8 mg/mL
2 g single, intravenous
CEFOPERAZONE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
211.62 mg × h/L per 1.73 m²
1 g single, intravenous
CEFOPERAZONE serum
Homo sapiens
421.63 mg × h/L per 1.73 m²
2 g single, intravenous
CEFOPERAZONE serum
Homo sapiens
1147.5 mg × h/L
100 mg/kg 3 times / day multiple, intravenous
CEFOPERAZONE serum
Homo sapiens
541.2 mg × h/L
50 mg/kg 3 times / day multiple, intravenous
CEFOPERAZONE serum
Homo sapiens
761.7 mg × h/L
100 mg/kg single, intravenous
CEFOPERAZONE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.649 h
1 g single, intravenous
CEFOPERAZONE serum
Homo sapiens
2.044 h
2 g single, intravenous
CEFOPERAZONE serum
Homo sapiens
0.063 h
100 mg/kg 3 times / day multiple, intravenous
CEFOPERAZONE serum
Homo sapiens
0.185 h
50 mg/kg 3 times / day multiple, intravenous
CEFOPERAZONE serum
Homo sapiens
0.063 h
100 mg/kg single, intravenous
CEFOPERAZONE serum
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as victim

PubMed

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: Other
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
Record UNII
5FQG9774WD
Record Status Validated (UNII)
Record Version