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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 of CEFMETAZOLE SODIUM

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
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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.
Curative
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.
Curative
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.
Curative
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.
Curative
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

AUC

ValueDoseCo-administeredAnalytePopulation
151 μg × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.43 h
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
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
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
PubMed

PubMed

TitleDatePubMed
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
[A successful treatment of an infective endocarditis caused by methicillin-resistant Staphylococcus aureus with a combination of cefmetazole with fosfomycin].
1989 Sep
MRSA meningitis in postoperative patients. Report of 4 cases.
1990 Jun
Incidence of beta-lactamase production and antimicrobial susceptibility of anaerobic gram-negative rods isolated from pus specimens of orofacial odontogenic infections.
2001 Feb
[Immunological properties of S-1090, cefmatilen hydrochloride hydrate].
2001 May
[A three-year review of acute respiratory tract infections caused by Streptococcus milleri group].
2002 Mar
Significance of SIRS score in therapeutic strategy for acute appendicitis.
2002 Mar-Apr
Meningitis caused by Enterococcus gallinarum in patients with ventriculoperitoneal shunts.
2003 Dec
Enhancement of antimicrobial effects of various antibiotics against methicillin-resistant Staphylococcus aureus (MRSA) by combination with fosfomycin.
2003 Dec
[Successful combination therapy of teicoplanin with cefmetazole on postoperative cardiovascular MRSA infections: clinical report on two cases].
2003 Feb
[Detection of novel nucleotide substitutions resulting amino acid substitutions in TEM type beta-lactamase gene isolated from a clinically isolated extended spectrum beta-lactamases (ESBLs) productive Escherichia coli].
2003 Mar
Unmasking hypotension by beta lactam during dextran sulfate low-density lipoprotein apheresis.
2004 Dec
[Study of resistance mechanism on cefotaxime resistant Proteus mirabilis isolated from clinical specimens and its clinical background].
2004 Jan
Escherichia coli producing CTX-M-2 beta-lactamase in cattle, Japan.
2004 Jan
[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
Fluoroquinolone-resistant Salmonella Paratyphi A.
2005 Jan
Antimicrobial activity of antibiotics in combination with natural flavonoids against clinical extended-spectrum beta-lactamase (ESBL)-producing Klebsiella pneumoniae.
2005 Jul
Prediction of pharmacokinetics of antibiotics in patients with end-stage renal disease.
2006 Jul
LC/MS/MS method for the determination of trace amounts of cefmetazole and cefpodoxime proxetil contaminants in pharmaceutical manufacturing environments.
2006 Jun 16
Effects of air tourniquet on the antibiotics concentration, in bone marrow, injected just before the start of operation.
2007
[Fundamental study on the selection of antimicrobial prophylactic agents in abdominal surgery].
2007 Aug
Involvement of MRP4 (ABCC4) in the luminal efflux of ceftizoxime and cefazolin in the kidney.
2007 Jun
Humanization of excretory pathway in chimeric mice with humanized liver.
2007 Jun
Characterization of antimicrobial resistance patterns and class 1 integrons in Escherichia coli O26 isolated from humans and animals.
2007 Mar
[Pyometra as a cause of fever; report on two cases].
2007 May
Chimeric mice with humanized liver.
2008 Apr 3
Pneumomediastinum as first manifestation of emphysematous pyelonephritis in a patient who is non-diabetic.
2009
Risk factors for complications after laparoscopic surgery in colorectal cancer patients: experience of 401 cases at a single institution.
2009 Aug
Implementing a standard protocol to decrease the incidence of surgical site infections in rectal cancer surgery.
2010 Apr
Clostridium difficile bacteremia, Taiwan.
2010 Aug
The use of tacrolimus for recurrent lupus enteritis: a case report.
2010 May 24
Multicenter prospective randomized phase II study of antimicrobial prophylaxis in low-risk patients undergoing colon surgery.
2010 Oct
Patents

Sample Use Guides

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
MART.   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
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
MI  
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
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
Code System Code Type Description
EVMPD
SUB01118MIG
Created by admin on Fri Dec 15 16:17:01 UTC 2023 , Edited by admin on Fri Dec 15 16:17:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045590
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201195
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
SMS_ID
100000084966
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
DRUG BANK
DBSALT000391
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
PUBCHEM
23666711
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
RXCUI
203140
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY RxNorm
MERCK INDEX
m3197
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY Merck Index
USAN
Z-5
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
FDA UNII
37Y9VR4W7A
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
CHEBI
3490
Created by admin on Fri Dec 15 16:17:01 UTC 2023 , Edited by admin on Fri Dec 15 16:17:01 UTC 2023
PRIMARY
NSC
758171
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY
CAS
56796-39-5
Created by admin on Fri Dec 15 16:17:01 UTC 2023 , Edited by admin on Fri Dec 15 16:17:01 UTC 2023
PRIMARY
NCI_THESAURUS
C65298
Created by admin on Fri Dec 15 16:17:02 UTC 2023 , Edited by admin on Fri Dec 15 16:17:02 UTC 2023
PRIMARY