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 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;
	(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.¹² 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

It was made by reacting 7-ACA (7-aminocephalosporanic acid) with cyanoacetyl chloride in the presence of tributylamine.

References

"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.
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.

[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.

[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.

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