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(O)c3ccccc3)C(=O)N12- InChIKey
DYAIAHUQIPBDIP-UJBKNGIVSA-N- Molecular formula
- C18H18N6O8S3
- Average molar mass
- 542.6 g/mol
- Monoisotopic mass
- 542.03482507
Names & identifiers
- Preferred name
- (6R,7R)-7-[(2-hydroxy-2-phenyl-acetyl)amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- IUPAC
- (6R,7R)-7-[(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
SCHEMBL537693AKOS015909693(6R,7R)-7-[(2-hydroxy-2-phenyl-acetyl)amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(7R)-7-(2-Hydroxy-2-phenylacetylamino)-6-oxo-3-{[1-(sulfomethyl)(1,2,3,4-tetraazol-5-ylthio)]methyl}-2H,7H,7aH-azetidino[2,1-b]1,3-thiazine-4-carboxylic acidMonocidCefodiePratledMonocidurCEFONICIDSKF-750737-beta(r*)))-Cefonicid USP/EP/BP
Show more names
Cefonicid (free base)amino)-8-oxo-3-(((1-sulfomethyl)-1h-tetrazol-5-yl)thio)methyl)-,(6r-(6-alpha,
Database identifiers
- CAS
61270-58-4- PubChem CID
- 43592
Properties
Computed structural properties
- 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
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
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.
UsesA semi-synthetic cephalosporin antibiotic related to Cefamandole. Antibacterial
Upstream & downstream products
Upstream raw materials
Related reactions
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Compound notes
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