CEFMETAZOLE SODIUM

US Previously Marketed

First approved in 1989

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H16N7O5S3.Na
Molecular Weight	493.516
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CO[C@]1(NC(=O)CSCC#N)[C@H]2SCC(CSC3=NN=NN3C)=C(N2C1=O)C([O-])=O

InChI

InChIKey=BITQGIOJQWZUPL-PBCQUBLHSA-M

InChI=1S/C15H17N7O5S3.Na/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25;/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25);/q;+1/p-1/t13-,15+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C15H16N7O5S3
Molecular Weight	470.526
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2020609
Curator's Comment: description was created based on several sources, including: http://www.robholland.com/Nursing/Drug_Guide/data/monographframes/C039.html | http://en.pharmacodia.com/web/drug/1_7102.html

Cefmetazole is a semisynthetic cephamycin antibiotic. It has a broad spectrum of activity comparable to that of the second-generation cephalosporins, covering gram-positive, gram-negative, and anaerobic bacteria. Its bactericidal action results from inhibition of cell wall synthesis. It effectively treats abdominal and respiratory tract infections, pelvic inflammatory disease, urinary tract infections, skin and soft tissue infections and used for surgical prophylaxis, reducing or eliminating signs and symptoms of infection. Cefmetazole has a low frequency of adverse effects, and a side effect profile similar to that of other cephamycins. Adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3898066 \| https://www.ncbi.nlm.nih.gov/pubmed/3915273 \| https://www.ncbi.nlm.nih.gov/pubmed/3499861 \| https://www.ncbi.nlm.nih.gov/pubmed/3009484	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Intra-abdominal infections 50 Sources: http://www.tabletwise.com/us/zefazone-injectable	Curative	Approved 8583	Cefmetazon Approved Use Active against a wide range of gram-positive and gram-negative aerobic and anaerobic bacteria. Effectively treats abdominal and respiratory tract infections, pelvic inflammatory disease, urinary tract infections, skin and soft tissue infections and used for surgical prophylaxis, reducing or eliminating signs and symptoms of infection.
Urinary tract infections 207 Sources: http://www.robholland.com/Nursing/Drug_Guide/data/monographframes/C039.html	Curative	Approved 8583	Cefmetazon Approved Use Active against a wide range of gram-positive and gram-negative aerobic and anaerobic bacteria. Effectively treats abdominal and respiratory tract infections, pelvic inflammatory disease, urinary tract infections, skin and soft tissue infections and used for surgical prophylaxis, reducing or eliminating signs and symptoms of infection.
Respiratory tract infections 85 Sources: http://www.robholland.com/Nursing/Drug_Guide/data/monographframes/C039.html	Curative	Approved 8583	Cefmetazon Approved Use Active against a wide range of gram-positive and gram-negative aerobic and anaerobic bacteria. Effectively treats abdominal and respiratory tract infections, pelvic inflammatory disease, urinary tract infections, skin and soft tissue infections and used for surgical prophylaxis, reducing or eliminating signs and symptoms of infection.
Skin and soft tissue infections 33 Sources: http://www.robholland.com/Nursing/Drug_Guide/data/monographframes/C039.html	Curative	Approved 8583	Cefmetazon Approved Use Active against a wide range of gram-positive and gram-negative aerobic and anaerobic bacteria. Effectively treats abdominal and respiratory tract infections, pelvic inflammatory disease, urinary tract infections, skin and soft tissue infections and used for surgical prophylaxis, reducing or eliminating signs and symptoms of infection.
Gynecologic infections 19 Sources: http://www.tabletwise.com/us/zefazone-injectable	Curative	Approved 8583	Cefmetazon Approved Use Cefmetazole is used for Gynecologic infections, Intra-abdominal infections, Urinary tract infections, Respiratory tract infections, Skin infections, Soft tissue infections and other conditions.

AUC

Value	Dose	Analyte	Population
83.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2291659	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFMETAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
151 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2291659	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFMETAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
301 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2291659	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFMETAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2291659	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFMETAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.43 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2291659	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFMETAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2291659	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	CEFMETAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3489	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3489
ChemicalBook	CB9231320	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9231320
eMolecules	31587579	https://www.emolecules.com/cgi-bin/more?vid=31587579
eMolecules	36752375	https://www.emolecules.com/cgi-bin/more?vid=36752375
MolPort	MolPort-005-934-200	https://www.molport.com/shop/molecule-link/MolPort-005-934-200
ZINC	ZINC000003830417	http://zinc15.docking.org/substances/ZINC000003830417

PubMed

Title	Date	PubMed
Multicenter prospective randomized phase II study of antimicrobial prophylaxis in low-risk patients undergoing colon surgery.	2010-10	20872199
Clostridium difficile bacteremia, Taiwan.	2010-08	20678312
Involvement of multidrug resistance-associated protein 4 in efflux transport of prostaglandin E(2) across mouse blood-brain barrier and its inhibition by intravenous administration of cephalosporins.	2010-06	20194529
The use of tacrolimus for recurrent lupus enteritis: a case report.	2010-05-24	20497521
Implementing a standard protocol to decrease the incidence of surgical site infections in rectal cancer surgery.	2010-04	20339987
Virtual Screening of potential drug-like inhibitors against Lysine/DAP pathway of Mycobacterium tuberculosis.	2010-01-18	20122228
Risk factors for complications after laparoscopic surgery in colorectal cancer patients: experience of 401 cases at a single institution.	2009-08	19506946
Pneumomediastinum as first manifestation of emphysematous pyelonephritis in a patient who is non-diabetic.	2009	21754958
A human hepatocyte-bearing mouse: an animal model to predict drug metabolism and effectiveness in humans.	2009	19884982
Xanthogranulomatous pyelonephritis successfully treated with antibiotics only.	2008-12	19114330
Successful treatment of gastric perforation with thyrotoxic crisis.	2008-11	19091282
Klebsiella oxytoca bacteremia causing septic shock in recipients of hematopoietic stem cell transplant: Two case reports.	2008-09-18	18801186
Effect of plasma protein binding on in vitro-in vivo correlation of biliary excretion of drugs evaluated by sandwich-cultured rat hepatocytes.	2008-07	18388177
Simultaneous Klebsiella pneumoniae and amoebic liver abscess in an immunocompetent patient.	2008-05	18480655
Chimeric mice with humanized liver.	2008-04-03	18248870
Predominant contribution of rat organic anion transporting polypeptide-2 (Oatp2) to hepatic uptake of beta-lactam antibiotics.	2008-03	17891554
In vitro antimicrobial susceptibility of Mycobacterium abscessus in Korea.	2008-02	18303198
Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter.	2007-12	17939016
Specific antibiotic prophylaxis based on bile cultures is required to prevent postoperative infectious complications in pancreatoduodenectomy patients who have undergone preoperative biliary drainage.	2007-11	17726628
Lemierre syndrome: a case of postanginal sepsis.	2007-09	17939341
Change of drug excretory pathway by CCl4-induced liver dysfunction in rat.	2007-08-01	17544377
[Fundamental study on the selection of antimicrobial prophylactic agents in abdominal surgery].	2007-08	18018416
Randomized, multicenter trial of antibiotic prophylaxis in elective colorectal surgery: single dose vs 3 doses of a second-generation cephalosporin without metronidazole and oral antibiotics.	2007-07	17638804
Involvement of MRP4 (ABCC4) in the luminal efflux of ceftizoxime and cefazolin in the kidney.	2007-06	17344354
Humanization of excretory pathway in chimeric mice with humanized liver.	2007-06	17341479
[Pyometra as a cause of fever; report on two cases].	2007-05	17564120
Characterization of antimicrobial resistance patterns and class 1 integrons in Escherichia coli O26 isolated from humans and animals.	2007-03	17390416
[Clinical and bacterial analysis of pediatric urinary tract infection].	2007-01	17338310
Effects of air tourniquet on the antibiotics concentration, in bone marrow, injected just before the start of operation.	2007	17929134
Gemella morbillorum liver abscess.	2007	17577836
Application of chimeric mice with humanized liver for predictive ADME.	2007	17364883
Case report: infective endocarditis caused by Brevundimonas vesicularis.	2006-12-29	17194310
[Prophylactic effect of fosfomycin on postoperative infection in gastroenterological surgery].	2006-12	17334060
Verification of cefmetazole and cefpodoxime proxetil contamination to other pharmaceuticals by liquid chromatography-tandem mass spectrometry.	2006-10	17015995
Prediction of pharmacokinetics of antibiotics in patients with end-stage renal disease.	2006-07	16819188
Beta-lactam antibiotic-induced release of lipoteichoic acid from Staphylococcus aureus leads to activation of neutrophil granulocytes.	2006-06-27	16803618
LC/MS/MS method for the determination of trace amounts of cefmetazole and cefpodoxime proxetil contaminants in pharmaceutical manufacturing environments.	2006-06-16	16704914
Emergence and prevalence of beta-lactamase-producing Klebsiella pneumoniae resistant to cephems in Japan.	2006-06	16701983
Determination of cefmetazole residue at pharmaceutical manufacturing facilities by chemiluminescence flow injection analysis.	2006-05-03	16413735
[A case of multiple recurrence of Clostridium difficile-associated diarrhea--analysis of isolates from the patient using PCR ribotyping].	2006-02	16506665
In vitro activities of 16 antimicrobial agents against clinical isolates of extended-spectrum beta-lactamase-producing Escherichia coli and Klebsiella pneumoniae in two regional hospitals in Taiwan.	2006-02	16440125
Antimicrobial activity of antibiotics in combination with natural flavonoids against clinical extended-spectrum beta-lactamase (ESBL)-producing Klebsiella pneumoniae.	2005-07	16161024
[Surveillance of susceptibility of clinical isolates to cefmetazole between 2000 and 2003].	2005-06	16161756
The significance of the intraoperative repeated dosing of antimicrobials for preventing surgical wound infection in colorectal surgery.	2005	16133667
MRSA meningitis in postoperative patients. Report of 4 cases.	1990-06	2232144
[A successful treatment of an infective endocarditis caused by methicillin-resistant Staphylococcus aureus with a combination of cefmetazole with fosfomycin].	1989-09	2810754
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration].	1988-06	3172294
Myoclonic activity associated with cefmetazole, with a review of neurotoxicity of cephalosporins.	1988	3233864
Induction of IgG1 and IgE responses to protein-conjugated and unconjugated beta-lactam antibiotics in the mouse--efficacy of Freund's complete adjuvant.	1985-12-15	2416589
In vitro susceptibility of Mycobacterium fortuitum to N-formimidoyl thienamycin and several cephamycins.	1982-12	6961887

Patents

Sample Use Guides

In Vivo Use Guide

2 g every 8-1 2 hours for 5-14 days

Route of Administration: Intravenous

In Vitro Use Guide

Cefmetazole is stable to any type of bacterial beta-lactamases, it inhibited growth of Escherichia coli carrying R plasmids, Klebsiella spp., Proteus vulgaris, and Bacteroides fragilis at the concentration of less than 0.78 to 25.0 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:57 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:57 GMT 2025`
Record UNII	37Y9VR4W7A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFMETAZOLE SODIUM

Official Name

English

CEFMETAZOLE SODIUM SALT

Preferred Name

English

CEFMETAZOLE SODIUM [MART.]

Common Name

English

CEFMETAZOLE SODIUM [VANDF]

Common Name

English

CEFMETAZOLE SODIUM SALT [MI]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((((CYANOMETHYL)THIO)ACETYL)AMINO)-7-METHOXY-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, MONOSODIUM SALT, (6R-CIS)

Common Name

English

Cefmetazole sodium [WHO-DD]

Common Name

English

NSC-758171

Code

English

Sodium (6R,7S)-7-[2-[(cyanomethyl)thio]acetamido]-7-methoxy-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

CEFMETAZOLE SODIUM [ORANGE BOOK]

Common Name

English

ZEFAZONE

Brand Name

English

U-72791A

Code

English

CEFMETAZOLE SODIUM [USP MONOGRAPH]

Common Name

English

CEFMETAZOLE SODIUM [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357