7908. Prulifloxacin

Nomenclature

CAS number: 123447-62-1
6-Fluoro-1-methyl-7-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-1-piperazinyl]-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid; NM-441; Quisnon (Nippon Shinyaku); Sword (Meiji); Unidrox (Angelini).
C21H20FN3O6S; mol wt 461.46.
C 54.66%, H 4.37%, F 4.12%, N 9.11%, O 20.80%, S 6.95%.

Description and references

Fluoroquinolone antibacterial; prodrug for active metabolite, ulifloxacin. Prepn: M. Kise et al., EP 315828; eidem, US 5086049 (1989, 1992 both to Nippon Shinyaku); J. Segawa et al., J. Med. Chem. 35, 4727 (1992). Comparative in vivo activity: M. Ozaki et al., Antimicrob. Agents Chemother. 35, 2496 (1991). Clinical pharmacokinetics: M. Nakashima et al., J. Clin. Pharmacol. 34, 930 (1994). Clinical comparison with ciprofloxacin in chronic bronchitis: C. Grassi et al., Respiration 69, 217 (2002). Review of pharmacology: M. G. Matera, Pulm. Pharmacol. Ther. 19, 20-29 (2006); of clinical development: M. Cazzola et al., ibid. 30-37.

Chemical structure

Properties

Pale yellow powder from acetonitrile, mp 220° (dec).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs