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
Legal status	℞ (Prescription only)
Routes of administration	Intravenous, intramuscular, intramammary
Pharmacokinetic data
Protein binding	23 to 38%
Biological half-life	1.2 hours
Excretion	Renal (72%)
Identifiers
CAS Number	10206-21-0 Y
ATC code	J01DB10 (WHO) QJ51DB10 (WHO)
PubChem	CID: 91562
DrugBank	DB01414 Y
ChemSpider	82675 Y
UNII	FDM21QQ344 Y
KEGG	D07629 Y
ChEMBL	CHEMBL2104099
Chemical data
Formula	C13H13N3O6S
Molecular 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 Y Key:RRYMAQUWDLIUPV-BXKDBHETSA-N Y
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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. 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.