Active Ingredient History

NOW
  • Now
Fialuridine, or 1-(2-deoxy-2-fluoro-1-D-arabinofuranosyl)-5-iodouracil (FIAU), is a nucleoside analogue that was investigated as a potential therapy for hepatitis B virus infection. In a 1993 clinical study at the NIH, unexpected toxicity led to the death of 5 out of 15 patients from liver failure alongside lactic acidosis; two further participants required liver transplantation. It is suspected that the toxicity of fialuridine was a result of mitochondrial damage caused by the incorporation of fialuridine into mitochondrial DNA via its 3'-hydroxyl moiety, leading to impaired DNA synthesis. This toxicity was unusual in that it was not predicted by animal studies.   Wikipedia

  • SMILES: OC[C@H]1O[C@H]([C@@H](F)[C@@H]1O)N2C=C(I)C(=O)NC2=O
  • InChIKey: IPVFGAYTKQKGBM-BYPJNBLXSA-N
  • Mol. Mass: 372.09
  • ALogP: -1.27
  • ChEMBL Molecule:
More Chemistry
123i-fiau | 1-(2-deoxy-2-fluoro-beta-arabinofuranosyl)-5-iodouracil | 1-(2'fluoro-2'-deoxyarabinofuranosyl)-5-iodouracil | 2'-fluoro-5-iodoarauracil | fialuridine | fiau

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