8735. Sparfloxacin

Nomenclature

CAS number: 110871-86-8
rel-5-Amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid; AT-4140; CI-978; PD-131501; Spara (Dainippon); Zagam (Specia).
C19H22F2N4O3; mol wt 392.40.
C 58.16%, H 5.65%, F 9.68%, N 14.28%, O 12.23%.

Description and references

Fluorinated quinolone antibacterial. Prepn: J. Matsumoto et al., EP 221463; eidem, US 4795751 (1987, 1989 both to Dainippon). Synthesis and structure-activity relationship: T. Miyamoto et al., J. Med. Chem. 33, 1645 (1990). Antibacterial activity: S. Nakamura et al., Antimicrob. Agents Chemother. 33, 1167 (1989). Comparative in vitro antimicrobial spectrum: T. Kojima et al., ibid. 1980. Pharmacokinetics: S. Nakamura et al., ibid. 34, 89 (1990). Subacute toxicity studies: M. Yasuba et al., Chemotherapy 39, Suppl. 4, 180 (1991), C.A. 115, 247561d (1991); M. Iida et al., ibid. 195, C.A. 115, 247562e (1991).

Chemical structure

Properties

Crystals from chloroform + ethanol, mp 266-269° (dec). pKa1 6.25, pKa2 9.30.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs