Fialuridine

Fialuridine
Clinical data


ATC code	none
Identifiers
IUPAC name 1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]-5-iodopyrimidine-2,4-dione
Synonyms	2′-Fluoro-5-iodouracil
CAS Number	69123-98-4^N
PubChem (CID)	50313
ChemSpider	45627
UNII	53T7IN77LC^Y
KEGG	D04181^Y
ChEMBL	CHEMBL271475^N
NIAID ChemDB	070971
Chemical and physical data
Formula	C₉H₁₀FIN₂O₅
Molar mass	372.09 g/mol
3D model (Jmol)	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
^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 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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