Cefacetrile

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 ;
PubChem CID	91562;
DrugBank	DB01414 ;
ChemSpider	82675 ;
UNII	FDM21QQ344;
KEGG	D07629 ;
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 ; 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.[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.

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References

"Cefacetrile Summary Report" (PDF). European Medicines Agency, Committee for Veterinary Medicinal Products. 1998.
Haberfeld H, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-183-8.
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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[1] "Cefacetrile Summary Report" (PDF). European Medicines Agency, Committee for Veterinary Medicinal Products. 1998.

[AC-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.