Chemistry:Fialuridine

Short description: Chemical compound

Fialuridine

Clinical data
Other names	2′-Fluoro-5-iodouracil
ATC code	none
Identifiers
IUPAC name 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]-5-iodopyrimidine-2,4-dione
CAS Number	69123-98-4 N
PubChem CID	50313
ChemSpider	45627 N
UNII	53T7IN77LC
KEGG	D04181 Y
ChEMBL	ChEMBL271475 N
NIAID ChemDB	070971
Chemical and physical data
Formula	C9H10FIN2O5
Molar mass	372.091 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1c(c(=O)[nH]c(=O)n1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)I
InChI InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1 N Key:IPVFGAYTKQKGBM-BYPJNBLXSA-N N
NY (what is this?)  (verify)

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.