Grepafloxacin

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Grepafloxacin
Grepafloxacin.svg
Systematic (IUPAC) name
(RS)-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline- 3-carboxylic acid
Clinical data
AHFS/Drugs.com Multum Consumer Information
Legal status
?
Pharmacokinetic data
Protein binding 50%
Identifiers
CAS number 119914-60-2 YesY
ATC code J01MA11
PubChem CID 72474
DrugBank DB00365
ChemSpider 65391 YesY
UNII L1M1U2HC31 YesY
KEGG C11368 YesY
ChEMBL CHEMBL583 YesY
Chemical data
Formula C19H22FN3O3 
Mol. mass 359.395 g/mol
 YesY (what is this?)  (verify)

Grepafloxacin hydrochloride (trade name Raxar, Glaxo Wellcome) was an oral broad-spectrum fluoroquinolone antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn world wide from markets in 1999,[1][2] owing to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death.[3]

Clinical uses[edit]

Grepafloxacin was used for treating exacerbations of chronic bronchitis caused by susceptible bacteria (eg Haemophilus influenzae, Streptococcus pneumoniae, Moraxella catarrhalis),[4][5][6] community-acquired pneumonia (including those, in addition to the above germs, caused by Mycoplasma pneumoniae)[7][8] gonorrhea and non-gonococcal urethritis and cervicitis (for example caused by Chlamydia trachomatis or Ureaplasma urealyticum).[9][10]

See also[edit]

References[edit]

  1. ^ "Glaxo Wellcome voluntary withdrawn Raxar (Grepafloxacin)". Retrieved 2014-10-12. 
  2. ^ "Withdrawal of Product: RAXAR (grepafloxacin HCl) 600 mg Tablets, 400 mg Tablets, and 200 mg Tablets". U.S. Food and Drug Administation. Retrieved 2014-10-12. 
  3. ^ Sprandel, KA.; Rodvold, KA. (2003). "Safety and tolerability of fluoroquinolones.". Clin Cornerstone. Suppl 3: S29–36. PMID 14992418. 
  4. ^ Chodosh S, Lakshminarayan S, Swarz H, Breisch S (January 1998). "Efficacy and safety of a 10-day course of 400 or 600 milligrams of grepafloxacin once daily for treatment of acute bacterial exacerbations of chronic bronchitis: comparison with a 10-day course of 500 milligrams of ciprofloxacin twice daily". Antimicrob. Agents Chemother. 42 (1): 114–20. PMC 105465. PMID 9449270. Retrieved 2014-10-12. 
  5. ^ Langan CE, Cranfield R, Breisch S, Pettit R (December 1997). "Randomized, double-blind study of grepafloxacin versus amoxycillin in patients with acute bacterial exacerbations of chronic bronchitis". J. Antimicrob. Chemother. 40 Suppl A: 63–72. PMID 9484875. Retrieved 2014-10-12. 
  6. ^ Langan CE, Zuck P, Vogel F, McIvor A, Peirzchala W, Smakal M, Staley H, Marr C (October 1999). "Randomized, double-blind study of short-course (5 day) grepafloxacin versus 10 day clarithromycin in patients with acute bacterial exacerbations of chronic bronchitis". J. Antimicrob. Chemother. 44 (4): 515–23. PMID 10588313. Retrieved 2014-10-12. 
  7. ^ O'Doherty B, Dutchman DA, Pettit R, Maroli A (December 1997). "Randomized, double-blind, comparative study of grepafloxacin and amoxycillin in the treatment of patients with community-acquired pneumonia". J. Antimicrob. Chemother. 40 Suppl A: 73–81. PMID 9484876. Retrieved 2014-10-12. 
  8. ^ Felmingham D (March 2000). "Respiratory pathogens: assessing resistance patterns in Europe and the potential role of grepafloxacin as treatment of patients with infections caused by these organisms". J. Antimicrob. Chemother. 45: 1–8. PMID 10719006. Retrieved 2014-10-12. 
  9. ^ Ridgway GL, Salman H, Robbins MJ, Dencer C, Felmingham D (December 1997). "The in-vitro activity of grepafloxacin against Chlamydia spp., Mycoplasma spp., Ureaplasma urealyticum and Legionella spp". J. Antimicrob. Chemother. 40 Suppl A: 31–4. PMID 9484871. Retrieved 2014-10-12. 
  10. ^ McCormack WM, Martin DH, Hook EW, Jones RB (1998). "Daily oral grepafloxacin vs. twice daily oral doxycycline in the treatment of Chlamydia trachomatis endocervical infection". Infect Dis Obstet Gynecol 6 (3): 109–15. doi:10.1155/S1064744998000210. PMC 1784789. PMID 9785106. Retrieved 2014-10-12.