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Antiinfective agent stubs
Fialuridine
Другие языки:

Fialuridine

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Fialuridine
Skeletal formula
Ball-and-stick model
Clinical data
Other names 2′-Fluoro-5-iodouracil
ATC code
  • none
Identifiers
  • 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]-5-iodopyrimidine-2,4-dione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
Chemical and physical data
Formula C9H10FIN2O5
Molar mass 372.091 g·mol−1
3D model (JSmol)
  • c1c(c(=O)[nH]c(=O)n1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)I
  • 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
 ☒NcheckY (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.


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