Temafloxacin

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Temafloxacin
File:Temafloxacin.png
Systematic (IUPAC) name
1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
Clinical data
Trade names Omniflox
Legal status
  • Withdrawn
Routes of
administration		 Oral
Identifiers
ATC code J01MA05 (WHO)
PubChem CID: 60021
DrugBank DB01405 N
ChemSpider 54143 YesY
UNII 1WZ12GTT67 N
KEGG D02469 N
ChEBI CHEBI:77788 N
ChEMBL CHEMBL277100 YesY
Chemical data
Formula C21H18F3N3O3
Molecular mass 417.381 g/mol
  • 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) YesY
  • Key:QKDHBVNJCZBTMR-UHFFFAOYSA-N YesY
 NYesY (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Temafloxacin (marketed by Abbott Laboratories as Omniflox) is a fluoroquinolone antibiotic drug which was withdrawn from sale in the United States shortly after its approval in 1992 because of serious adverse effects resulting in three deaths.[1][2] It is not marketed in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.

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

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External links

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