DrugBank: Cefmetazole (DB00274)

targets (6) transporters (2) carriers (1)

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

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
KEGG Compound	C08103
PubChem Compound	42008
PubChem Substance	46504461
ChemSpider	38311
ChEBI	3489
ChEMBL	3489
Therapeutic Targets Database	DAP001179
Drug Product Database	0
Wikipedia	http://en.wikipedia.org/wiki/Cefmetazole

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 Gene: mecA Protein Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: mrcA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: mrcB Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: ftsI Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: dacA Protein Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: dacC Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

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:

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:

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

Organism class: bacterial
UniProt ID: P02919 Link_out

Gene: mrcB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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:

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:

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:

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 Gene: SLC15A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: SLC15A2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

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:

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:

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 Gene: ALB Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. 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

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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.