Cefacetrile

Cefacetrile

Systematic (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
Clinical data
Trade names	Celospor, Celtol, Cristacef
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous, intramuscular, intramammary
Legal status	℞ (Prescription only)
Pharmacokinetic data
Protein binding	23 to 38%
Biological half-life	1.2 hours
Excretion	Renal (72%)
Identifiers
CAS Number	10206-21-0
ATC code	J01DB10 (WHO) QJ51DB10
PubChem	CID 91562
DrugBank	DB01414
ChemSpider	82675
UNII	FDM21QQ344
KEGG	D07629
ChEMBL	CHEMBL2104099
Chemical data
Formula	C13H13N3O6S
Molar mass	339.325 g/mol
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 Key:RRYMAQUWDLIUPV-BXKDBHETSA-N
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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]

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 3-85200-183-8.
3. Horiuchi, N.; Oyakawa, Y.; Oka, R.; Fujiwara, T. (1980). "Clinical evaluation of cephacetrile (Celtol) for respiratory infections (author's transl)". The Japanese journal of antibiotics 33 (10): 1145–1155. PMID 7206219.