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Identification
Name Cefmetazole
Accession Number DB00274 (APRD00852)
Type small molecule
Groups approved
Description

A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted. [PubChem]

Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Cefmetazole sodium
  • Cefmetazolo [INN-Spanish]
  • Cefmetazolum [INN-Latin]
Brand names
  • Zefazone
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 56796-20-4
Weight Average: 471.534
Monoisotopic: 471.045328759
Chemical Formula C15H17N7O5S3
InChI Key InChIKey=SNBUBQHDYVFSQF-HIFRSBDPSA-N
InChI
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
Plain Text
IUPAC Name
(6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)CSCC#N)OC)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Ethers
  • Nitriles and Derivatives
  • Cephalosporins
Substructures
  • Ethers
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Nitriles and Derivatives
  • Aliphatic and Aryl Amines
  • Aminals and Derivatives
  • Beta Lactams
  • Enamines
  • Cyanides
  • Tetrazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Azetidines
  • Cyanamides
Pharmacology
Indication For the treatment of infections caused by susceptible organisms.
Pharmacodynamics Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive Proteus, Serratia, anaerobic gram-negative bacilli (including B. fragilis), and some E. coli, Klebsiella, and P. mirabilis, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.
Mechanism of action The bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Absorption Bioavailability is approximately 100% following intramuscular injection.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

No appreciable metabolism.

Route of elimination Not Available
Half life 1.50 ±0.14 hours
Clearance Not Available
Toxicity Oral LD50 in rats is 3,204 mg/kg. With other b-lactam antibiotics, adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers Not Available
Dosage forms
Form Route Strength
Powder, for solution Intramuscular
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility 94.2 mg/L PhysProp
logP -2.2 PhysProp
Predicted Properties
Property Value Source
water solubility 2.16e+00 g/l ALOGPS
logP -0.38 ALOGPS
logP -0.65 ChemAxon Molconvert
logS -2.34 ALOGPS
pKa 8.72 ChemAxon Molconvert
hydrogen acceptor count 9 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 163.33 ChemAxon Molconvert
rotatable bond count 9 ChemAxon Molconvert
refractivity 124.57 ChemAxon Molconvert
polarizability 44.50 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00910 Link_out
KEGG Compound C08103 Link_out
PubChem Compound 42008 Link_out
PubChem Substance 46504461 Link_out
ChemSpider 38311 Link_out
ChEBI 3489 Link_out
ChEMBL 3489 Link_out
Therapeutic Targets Database DAP001179 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefmetazole Link_out
ATC Codes
  • J01DC09
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (52.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Penicillin binding protein 2a

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: C1KC03 Link_out
Gene: mecA Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yokota T, Yoshida R, Utsui Y, Tajima M: Cefmetazole: a broad spectrum cephem antibiotic effective on methicillin- and cephem-resistant Staphylococcus aureus. Drugs Exp Clin Res. 1985;11(1):29-38. Pubmed

2. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)

Organism class: bacterial
UniProt ID: P02918 Link_out
Gene: mrcA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. Pubmed

3. Penicillin-binding protein 1B

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)

Organism class: bacterial
UniProt ID: P02919 Link_out
Gene: mrcB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. Pubmed

4. Peptidoglycan synthetase ftsI

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates

Organism class: bacterial
UniProt ID: P0AD68 Link_out
Gene: ftsI
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. Pubmed

5. Penicillin-binding protein 5 precursor

Pharmacological action: yes
Actions: inhibitor

Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors

Organism class: bacterial
UniProt ID: P0AEB2 Link_out
Gene: dacA
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. Pubmed

6. D-alanyl-D-alanine carboxypeptidase dacC

Pharmacological action: yes
Actions: inhibitor

Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors

Organism class: bacterial
UniProt ID: P08506 Link_out
Gene: dacC Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. de la Rosa EJ, de Pedro MA, Vazquez D: Penicillin binding proteins: role in initiation of murein synthesis in Escherichia coli. Proc Natl Acad Sci U S A. 1985 Sep;82(17):5632-5. Pubmed

Transporters

1. Oligopeptide transporter, small intestine isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

2. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

Carriers

1. Serum albumin

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:02

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.