Fialuridine

Fialuridine

Skeletal formula
Ball-and-stick model
Systematic (IUPAC) name
1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]-5-iodopyrimidine-2,4-dione
Identifiers
CAS Number	69123-98-4 N
ATC code	none
PubChem	CID: 50313
UNII	53T7IN77LC Y
KEGG	D04181 Y
ChEMBL	CHEMBL271475 N
NIAID ChemDB	070971
Synonyms	2′-Fluoro-5-iodouracil
Chemical data
Formula	C9H10FIN2O5
Molecular mass	372.09 g/mol
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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 1992 clinical study at the NIH, unexpected toxicity led to the death of 5 out of 15 patients from liver failure associated with lactic acidosis. This toxicity was unusual in that it was not predicted by animal studies. It is suspected that the drug's toxicity was due to its damaging mitochondria.