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

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
Induction of IgG1 and IgE responses to protein-conjugated and unconjugated beta-lactam antibiotics in the mouse--efficacy of Freund's complete adjuvant.	1985 Dec 15	2416589
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
[A successful treatment of an infective endocarditis caused by methicillin-resistant Staphylococcus aureus with a combination of cefmetazole with fosfomycin].	1989 Sep	2810754
MRSA meningitis in postoperative patients. Report of 4 cases.	1990 Jun	2232144
The significance of the intraoperative repeated dosing of antimicrobials for preventing surgical wound infection in colorectal surgery.	2005	16133667
Antimicrobial activity of antibiotics in combination with natural flavonoids against clinical extended-spectrum beta-lactamase (ESBL)-producing Klebsiella pneumoniae.	2005 Jul	16161024
[Surveillance of susceptibility of clinical isolates to cefmetazole between 2000 and 2003].	2005 Jun	16161756
[Prophylactic effect of fosfomycin on postoperative infection in gastroenterological surgery].	2006 Dec	17334060
Case report: infective endocarditis caused by Brevundimonas vesicularis.	2006 Dec 29	17194310
[A case of multiple recurrence of Clostridium difficile-associated diarrhea--analysis of isolates from the patient using PCR ribotyping].	2006 Feb	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 Feb	16440125
Prediction of pharmacokinetics of antibiotics in patients with end-stage renal disease.	2006 Jul	16819188
Emergence and prevalence of beta-lactamase-producing Klebsiella pneumoniae resistant to cephems in Japan.	2006 Jun	16701983
LC/MS/MS method for the determination of trace amounts of cefmetazole and cefpodoxime proxetil contaminants in pharmaceutical manufacturing environments.	2006 Jun 16	16704914
Beta-lactam antibiotic-induced release of lipoteichoic acid from Staphylococcus aureus leads to activation of neutrophil granulocytes.	2006 Jun 27	16803618
Determination of cefmetazole residue at pharmaceutical manufacturing facilities by chemiluminescence flow injection analysis.	2006 May 3	16413735
Verification of cefmetazole and cefpodoxime proxetil contamination to other pharmaceuticals by liquid chromatography-tandem mass spectrometry.	2006 Oct	17015995
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
[Fundamental study on the selection of antimicrobial prophylactic agents in abdominal surgery].	2007 Aug	18018416
Change of drug excretory pathway by CCl4-induced liver dysfunction in rat.	2007 Aug 1	17544377
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
Humanization of excretory pathway in chimeric mice with humanized liver.	2007 Jun	17341479
Characterization of antimicrobial resistance patterns and class 1 integrons in Escherichia coli O26 isolated from humans and animals.	2007 Mar	17390416
[Pyometra as a cause of fever; report on two cases].	2007 May	17564120
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
Lemierre syndrome: a case of postanginal sepsis.	2007 Sep	17939341
Chimeric mice with humanized liver.	2008 Apr 3	18248870
Xanthogranulomatous pyelonephritis successfully treated with antibiotics only.	2008 Dec	19114330
In vitro antimicrobial susceptibility of Mycobacterium abscessus in Korea.	2008 Feb	18303198
Effect of plasma protein binding on in vitro-in vivo correlation of biliary excretion of drugs evaluated by sandwich-cultured rat hepatocytes.	2008 Jul	18388177
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
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
Risk factors for complications after laparoscopic surgery in colorectal cancer patients: experience of 401 cases at a single institution.	2009 Aug	19506946
Implementing a standard protocol to decrease the incidence of surgical site infections in rectal cancer surgery.	2010 Apr	20339987
Clostridium difficile bacteremia, Taiwan.	2010 Aug	20678312
Virtual Screening of potential drug-like inhibitors against Lysine/DAP pathway of Mycobacterium tuberculosis.	2010 Jan 18	20122228
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 Jun	20194529
The use of tacrolimus for recurrent lupus enteritis: a case report.	2010 May 24	20497521
Multicenter prospective randomized phase II study of antimicrobial prophylaxis in low-risk patients undergoing colon surgery.	2010 Oct	20872199

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 SODIUM

Official 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

CEFMETAZOLE SODIUM SALT

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

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Code System Code Type Description

EVMPD

SUB01118MIG

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EPA CompTox

DTXSID5045590

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ChEMBL

CHEMBL1201195

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SMS_ID

100000084966

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DRUG BANK

DBSALT000391

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PUBCHEM

23666711

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RXCUI

203140

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RxNorm

MERCK INDEX

m3197

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Merck Index

USAN

Z-5

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FDA UNII

37Y9VR4W7A

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CHEBI

3490

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NSC

758171

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CAS

56796-39-5

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NCI_THESAURUS

C65298

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ACTIVE MOIETY


					3J962UJT8H

CEFMETAZOLE

SUBSTANCE RECORD


					37Y9VR4W7A

CEFMETAZOLE SODIUM

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2020609Curator'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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

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

T_1/2