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Cefacetrile

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(Redirected from Cephacetrile) Chemical compound Pharmaceutical compound
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--
    8-oxo-5-thia-1-azabicyclooct-2-ene-2-
    carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.030.449 Edit this at Wikidata
Chemical and physical data
FormulaC13H13N3O6S
Molar mass339.32 g·mol
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS12NC(=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
  • Key:RRYMAQUWDLIUPV-BXKDBHETSA-N
  (verify)

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. Cefacetrile is marketed under the trade names Celospor, Celtol, and Cristacef, and as Vetimast for the treatment of mammary infections in lactating cows.

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. Archived from the original (PDF) on 2020-05-26. Retrieved 2012-01-25.
  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). "". The Japanese Journal of Antibiotics. 33 (10): 1145–55. PMID 7206219.
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
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