1919. Cefcapene Pivoxil

Nomenclature

CAS number: 105889-45-0
(6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy)methyl ester; (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-pentenoylamino]-3-(carbamoyloxymethyl)-3-cephem-4-carboxylic acid pivaloyloxymethyl ester; S-1108; Flumax (Shionogi).
C23H29N5O8S2; mol wt 567.64.
C 48.67%, H 5.15%, N 12.34%, O 22.55%, S 11.30%.

Description and references

Orally absorbed cephalosporin; ester prodrug of the active free acid metabolite, cefcapene. Prepn: Y. Hamashima et al., BE 904517; idem et al., US 4731361 (1986, 1988 both to Shionogi); K. Ishikura et al., J. Antibiot. 47, 466 (1994). In vitro activity and stability of the free acid: H. C. Neu et al., Antimicrob. Agents Chemother. 36, 1336 (1992). Metabolism: K. Totsuka et al., ibid. 757. Safety and pharmacokinetics: M. Nakashima et al., ibid. 762.

Chemical structure

Derivative

Free acid.

Nomenclature

CAS number: 135889-00-8
S-1006.
C17H19N5O6S2; mol wt 453.49.
C 45.02%, H 4.22%, N 15.44%, O 21.17%, S 14.14%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins