Cefonicid

Cefonicide (or cefonicid) is a cephalosporin antibiotic.[1]

Cefonicid
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601206
ATC code
Identifiers
IUPAC name
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H18N6O8S3
Molar mass542.56 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4CS(=O)(=O)O)C(=O)O
InChI
  • InChI=1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1 Y
  • Key:DYAIAHUQIPBDIP-AXAPSJFSSA-N Y
  (verify)

It has a density of 1.92g/cm3.

Synthesis

Injectable semi-synthetic cephalosporin antibiotic related to cefamandole, q.v.

Cefonicid synthesis:[2][3][4]

Cefonicid is synthesized conveniently by nucleophilic displacement of the 3-acetoxy moiety of 1 with the appropriately substituted tetrazole thiole 2. The mandelic acid amide C-7 side chain is reminiscent of cefamandole.

See also

References
  1. Saltiel E, Brogden RN (September 1986). "Cefonicid. A review of its antibacterial activity, pharmacological properties and therapeutic use". Drugs. 32 (3): 222–59. doi:10.2165/00003495-198632030-00002. PMID 3530703.
  2. DE 2611270, Berges, David Alan, "Cephalosporin-Derivate [Cephalosporin derivatives]", published 1976-09-30, assigned to SmithKline Corp.
  3. D. A. Berges, U.S. Patent 4,048,311 (1977 to Smith Kline).
  4. U.S. Patent 4,093,723, U.S. Patent 4,159,373 (1978, 1979 both to Smith Kline).
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