Garenoxacin
Title: Garenoxacin
CAS Registry Number: 194804-75-6
CAS Name: 1-Cyclopropyl-8-(difluoromethoxy)-7-[(1R)-2,3-dihydro-1-methyl-1H-isoindol-5-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
Manufacturers' Codes: T-3811
Molecular Formula: C23H20F2N2O4
Molecular Weight: 426.41
Percent Composition: C 64.78%, H 4.73%, F 8.91%, N 6.57%, O 15.01%
Literature References: Des-F(6)-quinolone antibacterial; topoisomerase II inhibitor. Prepn: Y. Todo et al., WO 9729102; eidem, US 6025370 (1997, 2000 both to Toyama); and antibacterial activity: K. Hayashi et al., Arzneim.-Forsch. 52, 903 (2002). HPLC determn in serum: D. Xuan et al., J. Chromatogr. B 765, 37 (2001). Mechanism of action study: D. Ince et al., Antimicrob. Agents Chemother. 46, 3370 (2002). Comparative antimicrobial spectra: M. Takahata et al., ibid. 43, 1077 (1999); M. Bassetti et al., ibid. 46, 234 (2002). Clinical pharmacokinetics: D. A. Gajjar et al., ibid. 47, 2256 (2003); and pharmacodynamics: S. Van Wart et al., ibid. 48, 4766 (2004). Toxicology study: A. Nagai et al., J. Toxicol. Sci. 27, 219 (2002). Review of pharmacology and therapeutic potential: R. Frechette, Curr. Opin. Invest. Drugs 2, 1706-1711 (2001).
Properties: Pale yellow plates from ethanol as 0.25 hydrate, mp 226-227°. [a]D27 -9.0° (c = 0.10 in N,N-dimethylformamide). Also reported as hydrate, mp 234-235°.
Melting point: mp 226-227°; mp 234-235°
Optical Rotation: [a]D27 -9.0° (c = 0.10 in N,N-dimethylformamide)
 
Derivative Type: Methanesulfonate
CAS Registry Number: 223652-82-2; 223652-90-2 (monohydrate)
Additional Names: Garenoxacin mesylate
Manufacturers' Codes: BMS-284756; T-3811ME
Molecular Formula: C23H20F2N2O4.CH4O3S
Molecular Weight: 522.52
Percent Composition: C 55.17%, H 4.63%, F 7.27%, N 5.36%, O 21.43%, S 6.14%
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Quinolones and Analogs; Topoisomerase II Inhibitor.

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