1976. Cephaloglycin

Nomenclature

CAS number: 3577-01-3
(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2R)-aminophenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetate (ester); 7-(d-2-amino-2-phenylacetamido)-3-acetoxymethyl-Δ3-cephem-4-carboxylic acid; 7-(d-α-aminophenylacetamido) cephalosporanic acid; Kefglycin (Lilly).
C18H19N3O6S; mol wt 405.42.
C 53.33%, H 4.72%, N 10.36%, O 23.68%, S 7.91%.

Description and references

Semi-synthetic cephalosporin antibiotic. Prepn: BE 635137; F. W. Wall et al., US 3422103 (1964, 1969 both to Glaxo); GB 1017624 (1966 to Merck & Co.); Spencer et al., J. Med. Chem. 9, 746 (1966); of d- and dl-forms: GB 985747 (1965 to Lilly); Kurita et al., J. Antibiot. 19A, 243 (1966). Metabolism and pharmacokinetics in man: J. Haginaka et al., J. Antibiot. 33, 236 (1980).

Chemical structure

Derivative

Dihydrate.

Nomenclature

CAS number: 22202-75-1
Kafocin (Lilly).

Properties

Crystalline powder, mp 223-250° (dec). uv max (2% DMF): 258 nm (E1%1cm 166). Isoelectric point and pH of maximum stability: 4.5.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins