Cefminox
Basic information
- CAS
84305-41-9- Standard SMILES
CO[C@@]1(NC(=O)CSC[C@@H](N)C(=O)O)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@@H]21- InChIKey
JSDXOWVAHXDYCU-VXSYNFHWSA-N- Molecular formula
- C16H21N7O7S3
- Average molar mass
- 519.6 g/mol
- Monoisotopic mass
- 519.06645956
Overview
Cefminox is a second-generation cephamycin antibiotic having [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and 2-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}acetamido side-groups located respectively at positions 3 and 7beta of the cephem nucleus. A broad-spectrum bactericide, it is especially effective against Gram-negative and anaerobic bacteria. It is a member of tetrazoles and a cephamycin. It is a conjugate acid of a cefminox(1-).
Names & identifiers
- Preferred name
- Cefminox
- IUPAC
- (6R,7S)-7-[[2-[(2S)-2-amino-2-carboxyethyl]sulfanylacetyl]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
- CEFMINOX
- Molecular formula
- C16H21N7O7S3
- Molecular weight
- 519.58
Names & synonyms
Cefminox84305-41-9CefminoxumCMNXMT 141Mt-141MT-141 FREE ACIDPW08Y13465CHEBI:135817DTXSID3010161745-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((((2S)-2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R,7S)-(6R,7S)-7-[[2-[(2S)-2-amino-3-hydroxy-3-oxopropyl]sulfanylacetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Show more names
(6R,7S)-7-[[[[(S)-2-Amino-2-carboxyethyl]thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,6β)-7α-[[[[(S)-2-Amino-2-carboxyethyl]thio]acetyl]amino]-7β-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]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-[[[[(2S)-2-amino-2-carboxyethyl]thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-
Properties
Computed structural properties
- XLogP
- -4
- Topological polar surface area
- 279 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 11
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 862
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Physicochemical properties
- Density
- 1.86 · 1.86±0.1 g/cm3(Predicted)
- pka
- 2.05 · 2.05±0.10(Predicted)
- FDA UNII
- 8 Y13465 · PW08Y13465
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of ActionCefminox is a β-lactam cephalosporin that binds and inactivates bacterial penicillin-binding proteins (PBPs), inhibiting peptidoglycan cell-wall synthesis.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications
UsesCefminox was found to dramatically inhibit growth of PASMCs with no obvious cytotoxicity. Growth inhibition by cefminox was partially reversed by both the IP antagonist RO113842 and the PPARγ antagonist GW9662.
Additional notes
DefinitionChEBI: Cefminox is a second-generation cephamycin antibiotic having [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and 2-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}acetamido side-groups located respectively at positions 3 and 7beta of the cephem nucleus. A broad-spectrum bactericide, it is especially effective against Gram-negative and anaerobic bacteria. It is a cephamycin and a member of tetrazoles. It is a conjugate acid of a cefminox(1-).
Related reactions
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Compound notes
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