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Identification
NameCefmetazole
Accession NumberDB00274  (APRD00852)
TypeSmall Molecule
GroupsApproved
DescriptionA 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
Synonyms
(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefmetazolo
Cefmetazolum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ZefazoneNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefmetazole sodium
56796-39-5
Thumb
  • InChI Key: BITQGIOJQWZUPL-PBCQUBLHSA-M
  • Monoisotopic Mass: 493.027273402
  • Average Mass: 493.516
DBSALT000391
Categories
UNII3J962UJT8H
CAS number56796-20-4
WeightAverage: 471.534
Monoisotopic: 471.045328759
Chemical FormulaC15H17N7O5S3
InChI KeyInChIKey=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
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Alkylarylthioether
  • Meta-thiazine
  • Heteroaromatic compound
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of infections caused by susceptible organisms.
PharmacodynamicsCefmetazole 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 actionThe bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Related Articles
AbsorptionBioavailability is approximately 100% following intramuscular injection.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

No appreciable metabolism.

Route of eliminationNot Available
Half life1.50 ±0.14 hours
ClearanceNot Available
ToxicityOral 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8407
Blood Brain Barrier-0.9932
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8283
P-glycoprotein inhibitor INon-inhibitor0.8047
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.8723
CYP450 2C9 substrateNon-substrate0.8274
CYP450 2D6 substrateNon-substrate0.8182
CYP450 3A4 substrateSubstrate0.5951
CYP450 1A2 substrateNon-inhibitor0.8575
CYP450 2C9 inhibitorNon-inhibitor0.82
CYP450 2D6 inhibitorNon-inhibitor0.895
CYP450 2C19 inhibitorNon-inhibitor0.8093
CYP450 3A4 inhibitorNon-inhibitor0.8551
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6417
Ames testNon AMES toxic0.8271
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9062
Rat acute toxicity2.2638 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9715
hERG inhibition (predictor II)Non-inhibitor0.7599
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility94.2 mg/LNot Available
logP-0.60SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility2.16 mg/mLALOGPS
logP-0.38ALOGPS
logP-0.65ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.38ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area163.33 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.57 m3·mol-1ChemAxon
Polarizability44.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01DC09
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.2 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolCefmetazole may increase the anticoagulant activities of Acenocoumarol.
DicoumarolCefmetazole may increase the anticoagulant activities of Dicoumarol.
Ethyl biscoumacetateCefmetazole may increase the anticoagulant activities of Ethyl biscoumacetate.
PhenindioneCefmetazole may increase the anticoagulant activities of Phenindione.
PhenprocoumonCefmetazole may increase the anticoagulant activities of Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefmetazole.
ProbenecidThe serum concentration of Cefmetazole can be increased when it is combined with Probenecid.
WarfarinCefmetazole may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
mecA
Uniprot ID:
C1KC03
Molecular Weight:
54918.915 Da
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:3915273 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
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).
Gene Name:
mrcA
Uniprot ID:
P02918
Molecular Weight:
93635.545 Da
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:3898066 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
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).
Gene Name:
mrcB
Uniprot ID:
P02919
Molecular Weight:
94291.875 Da
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:3898066 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Peptidoglycan glycosyltransferase activity
Specific Function:
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors (PubMed:7030331). Required for localization of FtsN (PubMed:9282742).
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular Weight:
63876.925 Da
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:3898066 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name:
dacA
Uniprot ID:
P0AEB2
Molecular Weight:
44443.62 Da
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:3898066 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name:
dacC
Uniprot ID:
P08506
Molecular Weight:
43608.595 Da
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:3898066 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Toxic substance binding
Specific Function:
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. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [PubMed:3339510 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
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.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
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:15567297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
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:15567297 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23