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Grepafloxacin: Wikis


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1 : 1 mixture (racemate)
Systematic (IUPAC) name
(RS)-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline- 3-carboxylic acid
CAS number 119914-60-2
ATC code J01MA11
PubChem 72474
DrugBank APRD01003
Chemical data
Formula C 19H22FN3O3  
Mol. mass 359.395 g/mol
Pharmacokinetic data
Bioavailability  ?
Protein binding 50%
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?
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Grepafloxacin hydrochloride (trade name Raxar, Glaxo Wellcome) was a oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn world wide from markets owing to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death.[1]

GlaxoSmithKline marketed Raxar at doses of 200 milligrams, 400 milligrams and 600 milligrams. Records filed with the U.S. Food and Drug Administration (FDA) showed that Raxar was cited as a suspect in the reported deaths of 13 patients. There were four deaths associated with patients who took Raxar in 600-milligram doses within the clinical trials submitted with the New Drug Application (NDA) in 1997. The package insert approved by the FDA stated that "there were no deaths or permanent disabilities" among those who took Raxar in 400-milligram doses. It was the FDA’s position that none of the noted fatalities "was shown to be attributable to Raxar." On Oct. 27, 1999, GlaxoSmithKline removed Raxar from clinical use citing to the fact that Raxar's effect on "QT interval prolongation" was unacceptably risky. [2]

Other drugs within this class (i.e. sparfloxacin, moxifloxacin, levofloxacin, gatifloxacin, gemifloxacin) have also been associated with QT interval prolongation, resulting in sudden death of the patient.[3]

See also


  1. ^ Sprandel, KA.; Rodvold, KA. (2003). "Safety and tolerability of fluoroquinolones.". Clin Cornerstone Suppl 3: S29-36. PMID 14992418.  
  2. ^
  3. ^ Fluoroquinolones and QT prolongation research continues Prolongation of the QT interval is associated with potentially life-threatening ventricular tachyarrhythmias such as torsades de pointes. by Kimberly Madewell, PharmD


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