CEFMETAZOLE

US Previously Marketed

First approved in 1989

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H17N7O5S3
Molecular Weight	471.534
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O

InChI

InChIKey=SNBUBQHDYVFSQF-HIFRSBDPSA-N

InChI=1S/C15H17N7O5S3/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)/t13-,15+/m1/s1

HIDE SMILES / InChI

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 233 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 8297

Conditions

Condition	Modality	Highest Phase	Product
Intra-abdominal infections 49 Sources: http://www.tabletwise.com/us/zefazone-injectable	Curative	Approved 8429	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 205 Sources: http://www.robholland.com/Nursing/Drug_Guide/data/monographframes/C039.html	Curative	Approved 8429	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 8429	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 8429	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 18 Sources: http://www.tabletwise.com/us/zefazone-injectable	Curative	Approved 8429	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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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

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
MolPort	MolPort-005-934-200	https://www.molport.com/shop/molecule-link/MolPort-005-934-200
ZINC	ZINC000003830417	http://zinc15.docking.org/substances/ZINC000003830417
eMolecules	31587579	https://www.emolecules.com/cgi-bin/more?vid=31587579
eMolecules	36752375	https://www.emolecules.com/cgi-bin/more?vid=36752375

PubMed

Title	Date	PubMed
In vitro susceptibility of Mycobacterium fortuitum to N-formimidoyl thienamycin and several cephamycins.	1982 Dec	6961887
Myoclonic activity associated with cefmetazole, with a review of neurotoxicity of cephalosporins.	1988	3233864
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration].	1988 Jun	3172294
Incidence of beta-lactamase production and antimicrobial susceptibility of anaerobic gram-negative rods isolated from pus specimens of orofacial odontogenic infections.	2001 Feb	11169133
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria].	2002 Feb	11977919
[A three-year review of acute respiratory tract infections caused by Streptococcus milleri group].	2002 Mar	11974885
Significance of SIRS score in therapeutic strategy for acute appendicitis.	2002 Mar-Apr	11995470
Influence of various antimicrobial agents on the intestinal flora in an intestinal MRSA-carrying rat model.	2004 Dec	15614458
[Feasibility of short-term antibiotic prophylaxis after pulmonary resection].	2004 Dec	15609652
Unmasking hypotension by beta lactam during dextran sulfate low-density lipoprotein apheresis.	2004 Dec	15558512
Escherichia coli producing CTX-M-2 beta-lactamase in cattle, Japan.	2004 Jan	15078599
[A case of probable bacterial translocation-associated sepsis in healthy adult].	2004 Mar	15103913
[A case of radiofrequency ablation therapy for recurrent hepatomas with tumor fever--efficacy of hepatic arterial infusion therapy with antibiotics and anticancer drugs].	2004 Oct	15553726
Mycobacterium goodii infections associated with surgical implants at Colorado hospital.	2004 Oct	15504281
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.	2005 Jan	15567297
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
Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter.	2007 Dec	17939016
[Clinical and bacterial analysis of pediatric urinary tract infection].	2007 Jan	17338310
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 Jul	17638804
Involvement of MRP4 (ABCC4) in the luminal efflux of ceftizoxime and cefazolin in the kidney.	2007 Jun	17344354
Specific antibiotic prophylaxis based on bile cultures is required to prevent postoperative infectious complications in pancreatoduodenectomy patients who have undergone preoperative biliary drainage.	2007 Nov	17726628
Xanthogranulomatous pyelonephritis successfully treated with antibiotics only.	2008 Dec	19114330
Predominant contribution of rat organic anion transporting polypeptide-2 (Oatp2) to hepatic uptake of beta-lactam antibiotics.	2008 Mar	17891554
Simultaneous Klebsiella pneumoniae and amoebic liver abscess in an immunocompetent patient.	2008 May	18480655
Successful treatment of gastric perforation with thyrotoxic crisis.	2008 Nov	19091282
Klebsiella oxytoca bacteremia causing septic shock in recipients of hematopoietic stem cell transplant: Two case reports.	2008 Sep 18	18801186

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.

Name

Type

Language

CEFMETAZOLE

Official Name

English

CEFMETAZOLE [USP-RS]

Common Name

English

(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-carboxylic acid

Systematic Name

English

CEFMETAZOLE [MART.]

Common Name

English

CEFMETAZOLE [VANDF]

Common Name

English

CEFMETAZOLE [USP MONOGRAPH]

Common Name

English

CEFMETAZOLE SODIUM [JAN]

Common Name

English

CEFMETAZOLE [USAN]

Common Name

English

U-72791

Code

English

Cefmetazole [WHO-DD]

Common Name

English

CEFMETAZOLE [USP IMPURITY]

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-, (6R-CIS)-

Common Name

English

CEFMETAZOLE [MI]

Common Name

English

cefmetazole [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01DC09