Temafloxacin

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Temafloxacin
Temafloxacin.png
Systematic (IUPAC) name
1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
Clinical data
Legal status
  • Withdrawn
Routes Oral
Identifiers
ATC code J01MA05
PubChem CID 60021
DrugBank DB01405
ChemSpider 54143 YesY
UNII 1WZ12GTT67 N
KEGG D02469 N
ChEBI CHEBI:77788 N
ChEMBL CHEMBL277100 YesY
Chemical data
Formula C21H18F3N3O3 
Mol. mass 417.381 g/mol
 N (what is this?)  (verify)

Temafloxacin (marketed by Abbott Laboratories as Omniflox) is a fluoroquinolone antibiotic drug which was withdrawn from sale in the United States shortly after its approval in 1992 because of serious adverse effects resulting in three deaths.[1][2]

History[edit]

Omniflox was approved to treat lower respiratory tract infections, genital and urinary infections like prostatitis, and skin infections in the United States by the Food and Drug Administration in January 1992. Severe adverse reactions, including allergic reactions and hemolytic anemia,[3] developed in about fifty patients during the first four months of its use, leading to three patient deaths. Abbott withdrew the drug from sale in June 1992.

Pharmacokinetic[edit]

Following oral administration the compound is well absorbed from the gastrointestinal tract. The oral bioavailability is greater than 90%. Temafloxacin has a good tissue penetration in various biological fluids and tissues, particularly in the respiratory tissues, nasal secretions, tonsils, prostate and bone.[4] In these districts the concentrations achieved are equal to or higher than those in serum.[5] The fluoroquinolone has a 7-8 hour half-life.[6] The penetration into the central nervous system (CNS)is less pronounced.[6]The escretion from the body is primarily due to the glomerular filtration.[7][8][9]

Clinical uses[edit]

The compound is indicated for treating lower respiratory tract infections (community-acquired pneumonia, exacerbations of chronic bronchitis), genital and urinary tract infections (prostatitis, gonococcal and non-gonococcal urethritis, cervicitis), skin and soft tissue infections.[6][10][11][12]

See also[edit]

References[edit]

  1. ^ "Recalling the Omniflox (Temafloxacin) Tablets" (pdf). Food and Drug Administration. 1992-06-05. Retrieved 2014-10-15. 
  2. ^ "ABBOTT WITHDRAWS TEMAFLOXACIN - Pharmaceutical industry news". The Pharmaletter. 1992-06-15. Retrieved 2014-10-16. 
  3. ^ Rubinstein, E. (2001). "History of quinolones and their side effects.". Chemotherapy. 47 Suppl 3: 3–8; discussion 44–8. doi:10.1159/000057838. PMID 11549783. 
  4. ^ Sorgel F, Naber KG, Kinzig M, Mahr G, Muth P (December 1991). "Comparative pharmacokinetics of ciprofloxacin and temafloxacin in humans: a review". Am. J. Med. 91 (6A): 51S–66S. PMID 1662896. 
  5. ^ Sörgel F (1992). "Penetration of temafloxacin into body tissues and fluids". Clin Pharmacokinet. 22 Suppl 1: 57–63. PMID 1319872. 
  6. ^ a b c Pankey GA (December 1991). "Temafloxacin: an overview". Am. J. Med. 91 (6A): 166S–172S. PMID 1662889. 
  7. ^ Granneman GR, Carpentier P, Morrison PJ, Pernet AG (February 1992). "Pharmacokinetics of temafloxacin in humans after multiple oral doses". Antimicrob. Agents Chemother. 36 (2): 378–86. PMC 188445. PMID 1318680. Retrieved 2014-10-17. 
  8. ^ Granneman GR, Braeckman R, Kraut J, Shupien S, Craft JC (November 1991). "Temafloxacin pharmacokinetics in subjects with normal and impaired renal function". Antimicrob. Agents Chemother. 35 (11): 2345–51. PMC 245383. PMID 1666497. Retrieved 2014-10-17. 
  9. ^ Dudley MN (December 1991). "A review of the pharmacokinetic profile of temafloxacin". J. Antimicrob. Chemother. 28 Suppl C: 55–64. PMID 1664830. Retrieved 2014-10-17. 
  10. ^ Gentry LO (December 1991). "Review of quinolones in the treatment of infections of the skin and skin structure". J. Antimicrob. Chemother. 28 Suppl C: 97–110. PMID 1787128. Retrieved 2014-10-17. 
  11. ^ Wise R (December 1991). "Comparative penetration of selected fluoroquinolones into respiratory tract fluids and tissues". Am. J. Med. 91 (6A): 67S–70S. PMID 1662897. 
  12. ^ Symonds WT, Nix DE (September 1992). "Lomefloxacin and temafloxacin: two new fluoroquinolone antimicrobials". Clin Pharm 11 (9): 753–66. PMID 1325892. 

External links[edit]