Chemistry:Fialuridine

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Short description: Chemical compound
Fialuridine
Skeletal formula
Ball-and-stick model
Clinical data
Other names2′-Fluoro-5-iodouracil
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
Chemical and physical data
FormulaC9H10FIN2O5
Molar mass372.091 g·mol−1
3D model (JSmol)
 ☒N☑Y (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.[1][2][3]

References

  1. "Mechanisms of drug-induced liver injury: from bedside to bench". Nature Reviews. Gastroenterology & Hepatology 8 (4): 202–11. April 2011. doi:10.1038/nrgastro.2011.22. PMID 21386809. 
  2. "Hepatic failure and lactic acidosis due to fialuridine (FIAU), an investigational nucleoside analogue for chronic hepatitis B". The New England Journal of Medicine 333 (17): 1099–105. October 1995. doi:10.1056/NEJM199510263331702. PMID 7565947. 
  3. Thomson, Larry (1 March 1994). "The Cure that Killed". Discover Magazine. http://discovermagazine.com/1994/mar/thecurethatkille345#.UnVB6ErVlkd. Retrieved 2 November 2013.