CEFOPERAZONE SODIUM

US Previously Marketed

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 Search

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	C25H26N9O8S2
Molecular Weight	644.659
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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050551s043lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 232 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6448021	Inhibitor 8228

Conditions

Condition	Modality	Highest Phase	Product
Respiratory tract infections 85 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050551s043lbl.pdf	Curative	Approved 8360	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
Peritonitis and other intra-abdominal infections 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050551s043lbl.pdf	Curative	Approved 8360	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
Sepsis 71 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050551s043lbl.pdf	Curative	Approved 8360	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
Skin and skin structure infections 80 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050551s043lbl.pdf	Curative	Approved 8360	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
Pelvic inflammatory disease 12 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050551s043lbl.pdf	Curative	Approved 8360	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
Urinary tract infections 204 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050551s043lbl.pdf	Curative	Approved 8360	CEFOBID Approved Use Urinary Tract Infections caused by Escherichia coli and Pseudomonas aeruginosa. Launch Date 4.064256E11

C_max

Value	Dose	Co-administered	Analyte	Population
154.9 mg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3619425	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3619425	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

Value	Dose	Analyte	Population
211.62 mg × h/L per 1.73 m² EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3619425	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3619425	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6644441	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6644441	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6644441	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

T_1/2

Value	Dose	Analyte	Population
1.649 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3619425	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3619425	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6644441	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6644441	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6644441	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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT4 145 OAT1 595 OAT2 144 OAT3 636	P-gp 1527 OATP1B3 347 BCRP 555

Drug as perpetrator

Target	Modality	Activity
OAT2 146	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 1330 uM]
OAT3 638	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [Ki 1890 uM]
OAT1 599	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [Ki 210 uM]
OAT4 145	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [Ki 2800 uM]

Drug as victim

Target	Modality	Activity
BCRP 555	substrate 3326 Sources: https://link.springer.com/article/10.1007/s11095-015-1641-2 Page: 5.0	yes
OATP1B3 347	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/21372390/	yes
P-gp 1527	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7679430/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3493	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3493
ChemicalBook	CB4752040	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4752040
MolPort	MolPort-006-069-122	https://www.molport.com/shop/molecule-link/MolPort-006-069-122
Selleck Chemicals	cefoperazone-cefobid	http://www.selleckchem.com/products/cefoperazone-cefobid.html
ZINC	ZINC000003830432	http://zinc15.docking.org/substances/ZINC000003830432
eMolecules	3715751	https://www.emolecules.com/cgi-bin/more?vid=3715751

PubMed

Title	Date	PubMed
Effect of cefaperazone/sulbactam and ampicillin/sulbactam on the in vitro activity of human erythrocyte glucose-6-phosphate dehydrogenase.	2001	11868906
Biodegradable polyhydroxyalkanoate implants for osteomyelitis therapy: in vitro antibiotic release.	2001	11403236
Prevalence and analysis of risk factors for infections caused by resistant Escherichia coli strains in Anhui, China.	2001 Aug	11545486
Development of a new protocol for the isolation and quantification of Arcobacter species from poultry products.	2001 Dec 30	11789937
Nosocomial bloodstream infection in pediatric patients: Siriraj Hospital, Bangkok; 1996-1999.	2001 Feb	11336072
Randomized, double-blind, controlled study of cefoperazone-sulbactam plus cotrimoxazole versus ceftazidime plus cotrimoxazole for the treatment of severe melioidosis.	2001 Jul 1	11389491
[Characterization of cefoperazone resistance gene on plasmid pFC in E. coli HX88108].	2001 Mar	12733347
[Clinical analysis of neutropenic fever associated with hematological disorders].	2001 Mar	11321778
Seroprevalence and antibiotic sensitivity of serotypes of Salmonella enterica in Greek pig herds.	2001 Mar 31	11327648
[Causative agents of bloodstream infections in children with neoplasm, in 5 hospitals of Santiago (1994-1998)].	2001 Nov	11836882
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.	2001 Oct	11570857
Calorimetric analysis of cephalosporins using an immobilized TEM-1 beta-lactamase on Ni2+ chelating sepharose fast flow.	2001 Sep 1	11520032
The history of antibiotics: the Japanese story.	2002 Jun	12111564
Pharmacokinetics of cefoperazone and sulbactam in liver transplant patients.	2002 Jun	12043952
In vitro antimicrobial susceptibility of 183 Pseudomonas aeruginosa strains isolated from dogs to selected antipseudomonal agents.	2002 May	12069272
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	12445561
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	12462425
Pseudomonas aeruginosa: resistance and therapy.	2002 Sep	12226802
Comparative study of antimicrobial resistance of Pseudomonas aeruginosa strains isolated from patients of Caracas and Asunción in a 4-year-period.	2002 Sep	12218262
[Efficacy and safety of cefoperazone/sulbactam in the treatment of children with mucoviscidosis during exacerbation of the bronchopulmonary process].	2003	15176099
Carbapenem-resistant Pseudomonas aeruginosa-carrying VIM-2 metallo-beta-lactamase determinants, Croatia.	2003 Aug	12971373
The status of drug resistance and ampC gene expression in Enterobacter cloacae.	2003 Aug	12935420
[Surveillance of susceptibility of clinical isolates to cefmetazole between 2000 and 2002].	2003 Dec	15007873
[Current data on antibiotic resistance of the most important bovine mastitis pathogens in Switzerland].	2003 Dec	14725183
[Comparative analysis of the effectiveness and costs of azithromycin and cefoperazone treatment of patients during COPD exacerbation].	2003 Jan	12712826
Hypersensitivity vasculitis induced by cefoperazone/sulbactam.	2003 Jan 3	12556245
[Changes of antimicrobial resistance among nonfermenting gram-negative bacilli isolated from intensive care units from 1994 to 2001 in China].	2003 Mar 10	12820914
[Assay of Acinetobacter SPP drug-resistance by Kirby-Bauer and Etest method].	2003 May	12754133
The susceptibility of non-fermentative Gram-negative bacilli to cefperazone and sulbactam compared with other antibacterial agents.	2003 Oct	14522108
Flies and Campylobacter infection of broiler flocks.	2004 Aug	15496257
Effective antibiotic regime for postoperative acute cholangitis in biliary atresia--an evolving scene.	2004 Dec	15616934
Derivatives of phosphate Schiff base transition metal complexes: synthesis, studies and biological activity.	2004 Jan	14670488
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	14713318
[Comparison of efficacy between ceftriaxone and cefoperazone plus sulbactam in peri-operative treatment of acute suppurative cholangitis].	2004 Nov 17	15631798
Acute interstitial nephritis due to cefoperazone.	2004 Sep	15213314
[Survey of the utilization and adverse effects of antibacterial drugs in patients admitted for respiratory diseases].	2005 Feb	15699017
[Distribution and drug-resistance of 3 500 gram-negative bacteria in Guangzhou].	2005 Feb	15698988

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: 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 Created by `admin` on `Wed Jul 05 23:53:40 UTC 2023` Edited by `admin` on `Wed Jul 05 23:53:40 UTC 2023`
Record UNII	5FQG9774WD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFOPERAZONE SODIUM

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

Common Name

English

CEFOPERAZONE SODIUM COMPONENT OF SULPERAZONE

Brand Name

English

Cefoperazone sodium [WHO-DD]

Common 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 [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 [EP IMPURITY]

Common Name

English

CEFOPERAZONE SODIUM [JAN]

Common Name

English

T-1551

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C357