Fialuridine

Fialuridine
Clinical data
Synonyms	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 ;
PubChem CID	50313;
ChemSpider	45627 ;
UNII	53T7IN77LC;
KEGG	D04181 ;
ChEMBL	CHEMBL271475 ;
NIAID ChemDB	070971;
Chemical and physical data
Formula	C9H10FIN2O5
Molar mass	372.09 g/mol
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 ; Key:IPVFGAYTKQKGBM-BYPJNBLXSA-N ;
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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 1993 clinical study at the NIH, unexpected toxicity led to the death of 5 out of 15 patients from liver failure associated with lactic acidosis; two further participants required liver transplantation. 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.^[1]^[2]^[3]

References

↑ Tujios S, Fontana RJ. Mechanisms of drug-induced liver injury: from bedside to bench. Nat Rev Gastroenterol Hepatol. 2011 Apr;8(4):202-11. Review. PMID 21386809
↑ 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): 1099–1105. doi:10.1056/NEJM199510263331702. PMID 7565947.
↑ Thomson, Larry (1 March 1994). "The Cure that Killed". Discover. Retrieved 2 November 2013.

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[1] Tujios S, Fontana RJ. Mechanisms of drug-induced liver injury: from bedside to bench. Nat Rev Gastroenterol Hepatol. 2011 Apr;8(4):202-11. Review. PMID 21386809

[2] 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): 1099–1105. doi:10.1056/NEJM199510263331702. PMID 7565947.

[3] Thomson, Larry (1 March 1994). "The Cure that Killed". Discover. Retrieved 2 November 2013.