4376. Gatifloxacin

Nomenclature

CAS number: 112811-59-3
1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid; Tequin (BMS); Zymar (Allergan).
C19H22FN3O4; mol wt 375.39.
C 60.79%, H 5.91%, F 5.06%, N 11.19%, O 17.05%.

Description and references

Fluorinated quinolone antibacterial. Prepn: K. Masuzawa et al., EP 230295; eidem, US 4980470 (1987, 1990 both to Kyorin); J. P. Sanchez et al., J. Med. Chem. 38, 4478 (1995); of the sesquihydrate: T. Matsumoto et al., US 5880283 (1999 to Kyorin). In vitro antibacterial activity: A. Bauernfeind, J. Antimicrob. Chemother. 40, 639 (1997); H. Fukuda et al., Antimicrob. Agents Chemother. 42, 1917 (1998). Clinical pharmacokinetics: M. Nakashima et al., ibid. 39, 2635 (1995). Clinical study in urinary tract infection: H. Nito, 10th Mediterranean Congr. Chemother. 1996, 327; in respiratory tract infection: S. Sethi, Expert Opin. Pharmacother. 4, 1847 (2003).

Chemical structure

Properties

Pale yellow prisms from methanol as hemihydrate, mp 162°.

Derivative

Sesquihydrate.

Nomenclature

CAS number: 180200-66-2
AM-1155.
C19H22FN3O4.1H2O; mol wt 384.40.
C 59.37%, H 6.03%, F 4.94%, N 10.93%, O 18.73%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs