4069. Fialuridine

Nomenclature

CAS number: 69123-98-4
1-(2-Deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione; 1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodouracil; 5-iodo-2′-fluoroarauracil; FIAU.
C9H10FIN2O5; mol wt 372.09.
C 29.05%, H 2.71%, F 5.11%, I 34.11%, N 7.53%, O 21.50%.

Description and references

Exptl antiviral agent; nucleoside analog with antihepatitis B activity. Prepn: K. A. Watanabe et al., J. Med. Chem. 22, 21 (1979). Antiviral activity: J. M. Colacino, C. Lopez, Antimicrob. Agents Chemother. 24, 505 (1983); K. A. Staschke et al., Antiviral Res. 23, 45 (1994). Clinical pharmacokinetics: R. R. Bowsher et al., Antimicrob. Agents Chemother. 38, 2134 (1994). Report of trial suspension: S. R. Ahmed, Lancet 342, 166 (1993). Evaluation of mechanism of hepatotoxicity: L. Cui et al., J. Clin. Invest. 95, 555 (1995). Clinical toxicological profile: W. Stevenson et al., Transplant. Proc. 27, 1219 (1995).

Chemical structure

Properties

Crystals from ethanol, mp 216-217°.