1972. Cephacetrile Sodium

Nomenclature

CAS number: 23239-41-0
(6R,7R)-3-[(Acetyloxy)methyl]-7-[(cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid monosodium salt; sodium 7-(2-cyanoacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate acetate (ester); sodium 7-(2-cyanoacetamido)cephalosporanic acid; Ciba 36278-Ba; Celospor (Novartis); Ubrocef (Novartis); Vetimast (Novartis).
C13H12N3NaO6S; mol wt 361.31.
C 43.21%, H 3.35%, N 11.63%, Na 6.36%, O 26.57%, S 8.87%.

Description and references

Semi-synthetic cephalosporin antibiotic. Prepn: NL 6600586; Bickel et al., US 3483197 (1966, 1969 both to Ciba). Activity studies: Knüsel et al., Antimicrob. Agents Chemother. 1970, 140; Neu et al., J. Antibiot. 25, 400 (1972). Pharmacokinetics and clinical results: Kradolfer et al., Schweiz. Med. Wochenschr. 103, 711 (1973); Riess et al., ibid. 718. Toxicology: Kradolfer et al., Antimicrob. Agents Chemother. 1970, 150. Review: Arzneim.-Forsch. 24, 1446-1533 (1974).

Chemical structure

Properties

White crystalline powder. LD50 in mice (mg/kg): 4500 ± 540 i.v.; 9100 ± 1500 s.c. (Kradolfer).

Derivative

Free acid.

Properties

Needles from acetone + ether, mp 168-170° (dec). uv max (0.1N NaHCO3): 260 nm (ε 9300).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins