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.
Garlic Garryine Gastrins Gastrodia Gastrodin

Garenoxacin
Garenoxacin.svg
Systematic (IUPAC) name
1-Cyclopropyl-8-(difluoromethoxy)-7-[(1R)-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Clinical data
Legal status  ?
Routes Oral
Identifiers
CAS number 194804-75-6 N
ATC code J01MA19
PubChem CID 124093
ChemSpider 110579 N
UNII V72H9867WB YesY
KEGG D04031 YesY
Chemical data
Formula C23H20F2N2O4 
Mol. mass 426.412 g/mol
 N (what is this?)  (verify)

Garenoxacin (INN) is a quinolone antibiotic for the treatment of Gram-positive and Gram-negative bacterial infections.

Garenoxacin was discovered by Toyama Chemical Co., Ltd. of Tokyo, Japan, and is currently being marketed in Japan under the tradename Geninax. Schering-Plough holds worldwide rights for garenoxacin, except for Japan, South Korea, and China.

On February 13, 2006, Schering-Plough announced that the United States Food and Drug Administration has accepted the New Drug Application (NDA) for garenoxacin, and has been granted a 10-month review.[1]

Schering-Plough later withdrew its application to the United States Food and Drug Administration, FDA, (August 20, 2006) for approval of the antibiotic Garenoxacin.[2]

The European Medicines Agency (EMEA) had also been formally notified by Schering-Plough Europe (July 28 2007) of its decision to withdraw the application for a centralized marketing authorization for garenoxacin as well.[3][4][5] Based on the CHMP review of the data regarding safety and efficacy (risk/benefit), the CHMP considered the application for garenoxacin to be unapprovable.[6]