Cefmetazole
Basic information
- CAS
56796-20-4- Standard SMILES
CO[C@@]1(NC(=O)CSCC#N)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@@H]21- InChIKey
SNBUBQHDYVFSQF-HIFRSBDPSA-N- Molecular formula
- C15H17N7O5S3
- Average molar mass
- 471.5 g/mol
- Monoisotopic mass
- 471.04533019
Overview
Cefmetazole is a second-generation cephalosporin antibiotic having N1-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7beta and 7alpha respectively of the parent cephem bicyclic structure. It has a role as an antibacterial drug. It is a conjugate acid of a cefmetazole(1-).
Names & identifiers
- Preferred name
- Cefmetazole
- IUPAC
- (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefmetazole
- Molecular formula
- C15H17N7O5S3
- Molecular weight
- 471.53
Names & synonyms
cefmetazole56796-20-4CefmetazoloCefmetazolum(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCefmetazol3J962UJT8HCHEBI:3489U-72791DTXSID7022756(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 acid5-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-, (6R-cis)-
Show more names
cs1170(6rCMZU 72791U 72791aSKF 83088Cefatrixine
(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(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(6R,7S)-7-((2-(cyanomethylsulfanyl)acetyl)amino)-7-methoxy-3-((1-methyltetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(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 acidRefChem:574974DTXCID502756J01DA40260-384-2
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 239 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 9
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 818
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
-2.2
-0.6
Solubility2.16e+00 g/L
Physical DescriptionSolid
Collision Cross Section192.97 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 163 · 163-165C
- Density
- 1.438 · 1.4380 (rough estimate)
- refractive index
- 1.74 · 1.7400 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly, Heated)
- form
- Solid
- pka
- 2.65 · 2.65±0.50(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Cefmetazole
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- wgk
- 2
- rtecs
- XI0372200
- hs_code
- 2941906000
- risk_code
- 36/37/38-42/43
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 26-36
- Hazard statements
- H315-H317-H319-H334-H335
- Precautionary statements
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
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 <i>Proteus</i>, <i>Serratia</i>, anaerobic gram-negative bacilli (including <i>B. fragilis</i>), and some <i>E. coli</i>, <i>Klebsiella</i>, and <i>P. mirabilis</i>, 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).
Biological Half-Life1.50 ±0.14 hours
Metabolism/MetabolitesNo appreciable metabolism.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionBioavailability is approximately 100% following intramuscular injection.
Cellular LocationsExtracellular
Applications
DescriptionCefmetazole is a cephamycin with a nonaromatic side chain at C-7. In addition to a fairly characteristic second-generation cephalosporin antimicrobial spectrum, it possess fairly significant anti-antiaerobic activity. The ejection of its C-3 side chain leads to alcohol intolerance of the disulfuram type and prolonged clotting times.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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