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 names	Celospor, Celtol, Cristacef
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous, intramuscular, intramammary
ATC code	J01DB10 (WHO) QJ51DB10 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	23 to 38%
Elimination half-life	1.2 hours
Excretion	Renal (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	10206-21-0 Y
PubChem CID	91562
DrugBank	DB01414 Y
ChemSpider	82675 Y
UNII	FDM21QQ344
KEGG	D07629 Y
ChEMBL	ChEMBL2104099
CompTox Dashboard (EPA)	DTXSID0022779
ECHA InfoCard	100.030.449
Chemical and physical data
Formula	C13H13N3O6S
Molar mass	339.32 g·mol−1
3D model (JSmol)	Interactive image
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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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.^{[citation needed]}