Cephacetrile

Synonym(s): 7-cyanacetamido-cephalosporanic acid  |  cefacetrile

Class: Beta-lactam (cephalosporin)

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	Active against Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli, Klebsiella sp., Salmonella typhimurium, and Proteus mirabilis
Description:	Semi-synthetic compound derived from cephalosporin C; well-tolerated when administered by intramuscular injection (vs cephalothin); used in veterinary medicine
Year first mentioned:	1972
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@H]([C@H]2SC1)NC(=O)CC#N
Isomeric SMILES:	CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC#N)SC1)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
InChI Key:	RRYMAQUWDLIUPV-BXKDBHETSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/91562

External links:
Guide to Pharmacology:	cefacetrile
Main Source:	https://www.jstage.jst.go.jp/article/antibiotics1968/25/7/25_7_400/_article/-char/en