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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H26N9O8S2.Na
Molecular Weight 667.6524
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFOPERAZONE SODIUM

SMILES

CCN1CCN(C(=O)C1=O)C(=N[C@]([H])(c2ccc(cc2)[O-])C(=N[C@]3([H])C(=O)N4C(=C(CS[C@]34[H])CSc5nnnn5C)C(=O)O)O)O.[Na+]

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 C25H26N9O8S2
Molecular Weight 644.6626
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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

4.064256E11
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

4.064256E11
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

4.064256E11
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

4.064256E11
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

4.064256E11
Curative
CEFOBID

Approved Use

Urinary Tract Infections caused by Escherichia coli and Pseudomonas aeruginosa.

Launch Date

4.064256E11
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
[The clinical investigation of bacteriology of chronic suppurative otitis media].
2001 Dec
[Characterization of cefoperazone resistance gene on plasmid pFC in E. coli HX88108].
2001 Mar
Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone.
2002
[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
In vitro and in situ evidence for the contribution of Labrasol and Gelucire 44/14 on transport of cephalexin and cefoperazone by rat intestine.
2002 Nov
Comparison of screening methods for TEM- and SHV-derived extended-spectrum beta-lactamase detection.
2002 Nov
First occurrence of transferable extended-spectrum beta-lactamase hydrolyzing cefoperazone in multiresistant nosocomial strains of Klebsiella pneumoniae from two hospitals in Czech and Slovak Republics.
2002 Oct
Antimicrobial susceptibility of major pathogens of orofacial odontogenic infections to 11 beta-lactam antibiotics.
2002 Oct
Pseudomonas aeruginosa: resistance and therapy.
2002 Sep
[Efficacy and safety of cefoperazone/sulbactam in the treatment of children with mucoviscidosis during exacerbation of the bronchopulmonary process].
2003
[Comparative clinical and epidemiological evaluation of beta-lactam antibiotics in the treatment of intraabdominal infections].
2003
[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
[Comparative analysis of the effectiveness and costs of azithromycin and cefoperazone treatment of patients during COPD exacerbation].
2003 Jan
Current status of drug resistance among gram-negative bacilli isolated from admitted cases in a tertiary care centre.
2003 Jan
Hypersensitivity vasculitis induced by cefoperazone/sulbactam.
2003 Jan 3
[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
Retrospective analysis of antibiotic susceptibility patterns of respiratory isolates of Pseudomonas aeruginosa in a Turkish University Hospital.
2003 Mar 7
[Assay of Acinetobacter SPP drug-resistance by Kirby-Bauer and Etest method].
2003 May
Preoperative antimicrobial administration for prevention of postoperative infection in patients with laparoscopic cholecystectomy.
2003 Oct
The susceptibility of non-fermentative Gram-negative bacilli to cefperazone and sulbactam compared with other antibacterial agents.
2003 Oct
Pharmacodynamics and pharmacokinetics of cefoperazone and cefamandole in dogs following single dose intravenous and intramuscular administration.
2003 Sep
Square-wave voltammetric determination of cefoperazone in a bacterial culture, pharmaceutical drug, milk, and urine.
2003 Sep
[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
Pacemaker lead endocarditis caused by Achromobacter xylosoxidans.
2004 Apr
Flies and Campylobacter infection of broiler flocks.
2004 Aug
Vibrio vulnificus in Taiwan.
2004 Aug
Effective antibiotic regime for postoperative acute cholangitis in biliary atresia--an evolving scene.
2004 Dec
Amebic liver abscess, Mirizzi syndrome, and acute hepatic failure.
2004 Feb
[Study of resistance mechanism on cefotaxime resistant Proteus mirabilis isolated from clinical specimens and its clinical background].
2004 Jan
Derivatives of phosphate Schiff base transition metal complexes: synthesis, studies and biological activity.
2004 Jan
Separation of cefoperazone enantiomers using beta-cyclodextrin as chiral additive by capillary zone electrophoresis.
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
Antibiotic susceptibility of coagulase-negative staphylococci isolated from goats' milk.
2004 Jun
In vitro activities of beta-lactam antibiotics alone and in combination with sulbactam against Gram-negative bacteria.
2004 Jun
In vitro activity of cefepime and cefpirome compared to other third-generation cephem antibiotics against gram-negative nosocomial pathogens.
2004 Nov
[Comparison of efficacy between ceftriaxone and cefoperazone plus sulbactam in peri-operative treatment of acute suppurative cholangitis].
2004 Nov 17
Pharmacokinetics of quinacrine in the treatment of prion disease.
2004 Nov 29
Arcobacter species in humans.
2004 Oct
Acute interstitial nephritis due to cefoperazone.
2004 Sep
[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

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 Jun 25 21:02:23 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:23 UTC 2021
Record UNII
5FQG9774WD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFOPERAZONE SODIUM
EP   MART.   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
CEFOPERAZONE SODIUM [ORANGE BOOK]
Common Name English
NSC-758173
Code English
CEFOPERAZONE SODIUM [EP MONOGRAPH]
Common Name English
CP-52,640-2
Code English
CEFOPERAZONE SODIUM SALT
MI  
Common Name English
CEFOPERAZONE SODIUM COMPONENT OF SULPERAZONE
Brand Name English
CEFOBID
Brand Name English
CP-526402
Code English
CEFOPERAZONE (AS SODIUM)
Common Name English
SULPERAZONE COMPONENT CEFOPERAZONE SODIUM
Brand Name English
CP-52640-2
Code English
CEFOPERAZONE SODIUM SALT [MI]
Common Name English
SODIUM CEFOPERAZONE
Common Name English
CEFOPERAZONE SODIUM [EP]
Common Name English
CEFOPERAZONE SODIUM [MART.]
Common Name English
CEFOPERAZONE SODIUM [USP MONOGRAPH]
Common Name English
CEFOPERAZONE SODIUM [VANDF]
Common Name English
CEFOPERAZONE SODIUM [USAN]
Common Name English
SODIUM (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-CARBOXYLATE
Systematic Name English
CEFOPERAZONE SODIUM [JAN]
Common Name English
CEFOPERAZONE SODIUM [WHO-DD]
Common Name English
T-1551
Code English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
Code System Code Type Description
DRUG BANK
DBSALT001470
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
PUBCHEM
23663974
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
263-751-5
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
EPA CompTox
62893-20-3
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
CAS
62893-20-3
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
FDA UNII
5FQG9774WD
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
EVMPD
SUB01122MIG
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
MERCK INDEX
M3201
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C47435
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL507674
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY
RXCUI
227214
Created by admin on Fri Jun 25 21:02:23 UTC 2021 , Edited by admin on Fri Jun 25 21:02:23 UTC 2021
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY