Trovafloxacin

Title: Trovafloxacin
CAS Registry Number: 147059-72-1
CAS Name: (1a,5a,6a)-7-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
Manufacturers' Codes: CP-99219
Molecular Formula: C20H15F3N4O3
Molecular Weight: 416.35
Percent Composition: C 57.70%, H 3.63%, F 13.69%, N 13.46%, O 11.53%
Literature References: Fluorinated quinolone antibacterial. Prepn: K. E. Brighty, US 5164402 (1992 to Pfizer). Voltammetric determn in urine and serum: J. L. Vílchez et al., J. Pharm. Biomed. Anal. 31, 465 (2003). Antibacterial spectrum in vitro: H. C. Neu, N.-X. Chin, Antimicrob. Agents Chemother. 38, 2615 (1994). Clinical pharmacokinetics: R. Teng et al., J. Antimicrob. Chemother. 36, 385 (1995). Evaluation in gonorrhea: E. W. Hook et al., Antimicrob. Agents Chemother. 40, 1720 (1996). Mechanism of hepatotoxicity: M. J. Liguori et al., Hepatology 41, 177 (2005).
Derivative Type: Hydrochloride
CAS Registry Number: 146961-34-4
Molecular Formula: C20H15F3N4O3.HCl
Molecular Weight: 452.81
Percent Composition: C 53.05%, H 3.56%, F 12.59%, N 12.37%, O 10.60%, Cl 7.83%
Properties: Pale yellow crystals from acetonitrile/methanol, mp 246° (dec).
Melting point: mp 246° (dec)
Derivative Type: Methanesulfonate
CAS Registry Number: 147059-75-4
Additional Names: Trovafloxacin mesylate
Manufacturers' Codes: CP-99219-27
Trademarks: Trovan
Molecular Formula: C20H15F3N4O3.CH3SO3H
Molecular Weight: 512.46
Percent Composition: C 49.22%, H 3.74%, F 11.12%, N 10.93%, O 18.73%, S 6.26%
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Quinolones and Analogs.
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Trovafloxacin
Trovafloxacin.svg
Systematic (IUPAC) name
7-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-[1,8] naphthyridine-3-carboxylic acid
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a605016
Legal status Withdrawn from market
Routes Oral, intravenous
Identifiers
CAS number 147059-72-1 YesY
ATC code J01MA13
PubChem CID 62959
DrugBank DB00685
ChemSpider 16736478 YesY
UNII 9F388J00UK YesY
KEGG D08654 YesY
ChEMBL CHEMBL428 YesY
Chemical data
Formula C20H15F3N4O3 
Mol. mass 416.353 g/mol
 YesY (what is this?)  (verify)

Trovafloxacin (sold as Trovan by Pfizer and Turvel by Laboratorios Almirall) is a broad spectrum antibiotic that inhibits the uncoiling of supercoiled DNA in various bacteria by blocking the activity of DNA gyrase and topoisomerase IV.[1] It was withdrawn from the market due to the risk of hepatotoxicity. It had better gram-positive bacterial coverage and less gram-negative coverage than the previous fluoroquinolones.