Fialuridine

Fialuridine

File:Fialuridine.png
Systematic (IUPAC) name
1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]-5-iodopyrimidine-2,4-dione
Identifiers
ATC code	none
PubChem	CID 50313
Synonyms	2′-Fluoro-5-iodouracil
Chemical data
Formula	C9H10FIN2O5
Molar mass	372.09 g/mol[[]]

Fialuridine, or 1-(2-deoxy-2-fluoro-1-D-arabinofuranosyl)-5-iodouracil (FIAU), is a nucleoside analogue. It was originally designed as a therapy for hepatitis B virus infection. Unexpected toxicity lead to the death of 5 out of 15 patients in a clinical study at the NIH from fulminant liver failure. This toxicity was unusual in that it was not predicted by animal studies.

References

• McKenzie R, Fried MW, Sallie R; et al. (1995). "Hepatic failure and lactic acidosis due to fialuridine (FIAU), an investigational nucleoside analogue for chronic hepatitis B". N. Engl. J. Med. 333 (17): 1099–105. doi:10.1056/NEJM199510263331702. PMID 7565947. CS1 maint: Explicit use of et al. (link) CS1 maint: Multiple names: authors list (link)
• Review of the Fialuridine (FIAU) Clinical Trials, Committee to Review the Fialuridine (FIAU/FIAC) Clinical Trials, Division of Health Sciences Policy INSTITUTE OF MEDICINE Frederick J. Manning and Morton Swartz, Editors NATIONAL ACADEMY PRESS Washington, D.C.1995