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).
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.