1986. Cephradine

Nomenclature

CAS number: 38821-53-3
(6R,7R)-7-[[(2R)-Amino-1,4-cyclohexadien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-[d-2-amino-2-(1,4-cyclohexadienyl)acetamido]desacetoxycephalosporanic acid; cefradine; SQ-11436; Cefro (Sankyo); Dexef (Dexo); Eskacef (GSK); Velocef (BMS); Zeefra (Bouchara-Recordati).
C16H19N3O4S; mol wt 349.40.
C 55.00%, H 5.48%, N 12.03%, O 18.32%, S 9.18%.

Description and references

A semisynthetic cephalosporin antibiotic. Prepn and activity data: Weisenborn et al., US 3485819 (1969 to Squibb); Dolfini et al., J. Med. Chem. 14, 117 (1971). Clinical trials: Limson et al., Curr. Ther. Res. 14, 101 (1972); Landa, ibid. 496. Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 5, 21-59 (1976). Review: W. E. Brown, J. R. Knill, in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 279-304.

Chemical structure

Derivative

Monohydrate.

Nomenclature

CAS number: 75975-70-1

Properties

Small, colorless crystals. mp 140-142° (dec). pK1 2.63; pK2 7.27. Sol in propylene glycol; slightly sol in acetone, ethanol. Insol in ether, chloroform, benzene, hexane.

Derivative

Dihydrate.

Nomenclature

CAS number: 31828-50-9
SQ-22022.

Properties

mp 183-185°.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins