Cefacetrile

Cefacetrile (INN, also spelled cephacetrile) is a broad-spectrum first generation cephalosporin antibiotic effective in gram-positive and gram-negative bacterial infections. It is a bacteriostatic antibiotic.[1][2] Cefacetrile is marketed under the trade names Celospor, Celtol, and Cristacef,[3] and as Vetimast for the treatment of mammary infections in lactating cows.[2]

Cefacetrile
Clinical data
Trade namesCelospor, Celtol, Cristacef
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intravenous, intramuscular, intramammary
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding23 to 38%
Elimination half-life1.2 hours
ExcretionRenal (72%)
Identifiers
IUPAC name
  • (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-
    8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-
    carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.030.449
Chemical and physical data
FormulaC13H13N3O6S
Molar mass339.32 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CC#N)COC(=O)C)C(=O)O
InChI
  • InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1 Y
  • Key:RRYMAQUWDLIUPV-BXKDBHETSA-N Y
  (verify)

Synthesis
Cefacetrile synthesis: NL 6600586 (1966 to Ciba-Geigy).

It was made by reacting 7-ACA (7-aminocephalosporanic acid) with cyanoacetyl chloride in the presence of tributylamine.

References
  1. "Cefacetrile Summary Report" (PDF). European Medicines Agency, Committee for Veterinary Medicinal Products. 1998.
  2. Haberfeld H, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-183-8.
  3. Horiuchi N, Oyakawa Y, Oka R, Fujiwara T (October 1980). "[Clinical evaluation of cephacetrile (Celtol) for respiratory infections (author's transl)]". The Japanese Journal of Antibiotics. 33 (10): 1145–55. PMID 7206219.
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