Temafloxacin

Last updated

Temafloxacin
Temafloxacin structure.svg
Clinical data
Trade names Omniflox
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • Withdrawn
Identifiers
  • 1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H18F3N3O3
Molar mass 417.388 g·mol−1
3D model (JSmol)
  • Fc1ccc(c(F)c1)N\3c2cc(c(F)cc2C(=O)C(/C(=O)O)=C/3)N4CC(NCC4)C
  • InChI=1S/C21H18F3N3O3/c1-11-9-26(5-4-25-11)19-8-18-13(7-16(19)24)20(28)14(21(29)30)10-27(18)17-3-2-12(22)6-15(17)23/h2-3,6-8,10-11,25H,4-5,9H2,1H3,(H,29,30) Yes check.svgY
  • Key:QKDHBVNJCZBTMR-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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Temafloxacin (marketed by Abbott Laboratories as Omniflox) is a fluoroquinolone antibiotic drug which was withdrawn from sale in the United States shortly after its approval in 1992 because of serious adverse effects resulting in three deaths.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] It is not marketed in Europe.

Contents

History

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 over 100 patients during the first four months of its use, leading to three patient deaths. Abbott withdrew the drug from sale in June 1992.

Pharmacokinetics

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 excretion from the body is primarily due to glomerular filtration in the kidneys. [7] [8] [9]

Clinical uses

The compound was 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

References

  1. ↑ "Recalling the Omniflox (Temafloxacin) Tablets" (PDF). Food and Drug Administration. 1992-06-05. Archived from the original (PDF) on June 6, 2011. 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): 3–8, discussion 44–8. doi:10.1159/000057838. PMID   11549783. S2CID   21890070.
  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. doi:10.1016/0002-9343(91)90312-L. PMID   1662896.
  5. ↑ Sörgel F (1992). "Penetration of temafloxacin into body tissues and fluids". Clin Pharmacokinet. 22 (Suppl 1): 57–63. doi:10.2165/00003088-199200221-00010. PMID   1319872. S2CID   32791009.
  6. 1 2 3 Pankey GA (December 1991). "Temafloxacin: an overview". Am. J. Med. 91 (6A): 166S –172S. doi:10.1016/0002-9343(91)90332-r. 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. doi:10.1128/aac.36.2.378. PMC   188445 . PMID   1318680.
  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. doi:10.1128/aac.35.11.2345. PMC   245383 . PMID   1666497.
  9. ↑ Dudley MN (December 1991). "A review of the pharmacokinetic profile of temafloxacin" . J. Antimicrob. Chemother. 28 Suppl C: 55–64. doi:10.1093/jac/28.suppl_c.55. 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. doi:10.1093/jac/28.suppl_C.97. 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. doi:10.1016/0002-9343(91)90313-M. PMID   1662897.
  12. ↑ Symonds WT, Nix DE (September 1992). "Lomefloxacin and temafloxacin: two new fluoroquinolone antimicrobials". Clin Pharm. 11 (9): 753–66. PMID   1325892.
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