Drug nameTemafloxacin
DescriptionTemafloxacin is a fluoroquinolone antibiotic drug which was withdrawn from sale in the U.S. shortly after its approval in 1992 because of serious adverse reactions resulting in three deaths. [Wikipedia]
DrugBankPrimary Accession Number: DB01405
DINNot available
TypeSmall Molecule, Withdrawn
IndicationFor the treatment of lower respiratory tract infections, genital and urinary infections like prostatitis, and skin infections.
Mechanism of ActionThe bactericidal action of temafloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.
AbsorptionStudies in healthy volunteers indicate that the average bioavailability of temafloxacin exceeds 90%, with little intersubject variability.
ToxicitySevere adverse reactions, including allergic reactions and hemolytic anemia, developed in about fifty patients during the first four months of its use, leading to three patient deaths
Protein BindingNot available
Interactions
RXListNot available
KEGGdrug: D02469 / compound: Not Available
PubChemcompound: 60021 / substance: 14831465
PharmGKBNot available
Metabolizing Enzymes
NameGeneEntrezIDUniprotSNP
Target
NameGeneEntrezIDSwissprotSNP
DNA gyrase subunit AgyrAGYRA_HAEINrs41274928 rs2273709 rs6917902 rs59298334 rs941849 rs45597237 rs45496798 rs41274936 rs41274934 rs35768540 rs35708170 rs35514919 rs35085988 rs34716183 rs11962520 rs9472022 rs4714672 rs3215697 rs2841640
DNA topoisomerase 4 subunit AparCPARC_HAEINrs41274928 rs2273709 rs6917902 rs59298334 rs941849 rs45597237 rs45496798 rs41274936 rs41274934 rs35768540 rs35708170 rs35514919 rs35085988 rs34716183 rs11962520 rs9472022 rs4714672 rs3215697 rs2841640 s6917902
FilesDB01405.mol | pdb_507034824834-0.pdb | sdf_9348931614996-0.sdf |
Smilesisomeric:
C[C@H]1CN(CCN1)C1=C(F)C=C2C(=O)C(=CN(C2=C1)C1=C(F)C=C(F)C=C1)C(O)=O
canonical:
CC1CN(CCN1)C1=C(F)C=C2C(=O)C(=CN(C2=C1)C1=C(F)C=C(F)C=C1)C(O)=O

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