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Basic information
- CAS
61270-58-4- Standard SMILES
O=C(O)C1=C(CSc2nnnn2CS(=O)(=O)O)CS[C@@H]2[C@H](NC(=O)[C@H](O)c3ccccc3)C(=O)N12- InChIKey
DYAIAHUQIPBDIP-AXAPSJFSSA-N- Molecular formula
- C18H18N6O8S3
- Average molar mass
- 542.6 g/mol
- Monoisotopic mass
- 542.03482507
Names & identifiers
- Preferred name
- Cefonicid
- IUPAC
- (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefonicid
- Molecular formula
- C18H18N6O8S3
- Molecular weight
- 542.57
Names & synonyms
CEFONICID61270-58-4CefonicidoCefonicidumMonocefCEFONICIDE6532B86WFG(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCHEBI:3491DTXSID7022758SK&F 75073(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-8-oxo-3-({[1-(sulfomethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Show more names
MonocidCefodiePratledMonocidurSKF-750737-beta(r*)))-Cefonicid USP/EP/BPCefonicid (free base)amino)-8-oxo-3-(((1-sulfomethyl)-1h-tetrazol-5-yl)thio)methyl)-,(6r-(6-alpha,
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-8-oxo-3-({[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-(((2R)-2-hydroxy-2-phenylacetyl)amino)-8-oxo-3-(((1-(sulfomethyl)-1H-tetrazol-5-yl)sulfanyl)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-(((2R)-2-hydroxy-2-phenylacetyl)amino)-8-oxo-3-((1-(sulfomethyl)tetrazol-5-yl)sulfanylmethyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-((2R)-2-hydroxy-2-phenylacetamido)-8-oxo-3-(((1-(sulfomethyl)-1H-1,2,3,4-tetrazol-5-yl)sulfanyl)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:124234DTXCID302758J01DA17SK&F75073
Properties
Computed structural propertiesFilling in
- XLogP
- -1.9
- Topological polar surface area
- 264 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 9
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 999
Experimental & physicochemical properties
Solubility8.95e-01 g/L
Physical DescriptionSolid
Collision Cross Section205.05 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Density
- 1.92 · 1.92±0.1 g/cm3(Predicted)
- pka
- -1.23 · -1.23±0.50(Predicted)
- FDA UNII
- 6532 B86WFG · 6532B86WFG
- ATC code
- 1 DC06 · J01DC06
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use；J01 - Antibacterials for systemic use；J01D - Other beta-lactam antibacterials；J01DC - Second-generation cephalosporins；J01DC06 - Cefonicid
QJ - Antiinfectives for systemic use；QJ01 - Antibacterials for systemic use；QJ01D - Other beta-lactam antibacterials；QJ01DC - Second-generation cephalosporins；QJ01DC06 - Cefonicid
Protein Binding98% bound to plasma proteins.
Pharmacodynamics
Cefonicid is a second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections.
Mechanism of Action
Cefonicid, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.
Biological Half-Life4.5 hours
Metabolism/MetabolitesNot metabolized.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Cellular LocationsExtracellular；Membrane
Applications
DescriptionCefonicid has an unesterified D-mandelic acid moiety at C-7 and a methylsulfothiotetrazole group at C-3. The latter is related to the MTT moiety mentioned above under cefamandole nafate; however, the clotting problems and Antabuse-like side effects associated with MTT have not been reported with cefonicid. The extra acid group in the C-3 side chain leads to this molecule being sold as an injectable disodium salt. Pain and discomfort at IM sites is experienced by some patients, as is a burning sensation and phlebitis. Cefonicid has a longer half-life than the other members of its group but achieves this at the price of somewhat lower potency against Gram-positive bacteria and aerobes. The drug is somewhat unstable, needs to be protected from light and heat, and may yellow or darken. If modest, however, this does not necessarily mean that the potency has decreased significantly, but overt precipitation does. Kirby-Bauer disk testing may overestimate the sensitivity of β-lactamase–producing bacteria to this agent, so some extra caution in interpretation of laboratory results is required.
Related reactions
1 records
Compound notes
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