For research use only. Not for therapeutic Use.
Fialuridine (Cat No.:R009440) is a nucleoside analog initially developed as an antiviral agent for treating hepatitis B virus (HBV) infections. It inhibits viral DNA polymerase by incorporating into viral DNA, causing chain termination and disrupting replication. Despite promising in vitro activity, clinical use was discontinued due to severe toxicity, including mitochondrial dysfunction and liver failure. Fialuridine remains a key compound in research, offering insights into nucleoside analog mechanisms, mitochondrial toxicity, and the development of safer antiviral therapies. Its study has significantly impacted antiviral drug design and preclinical safety evaluation.
| Catalog Number | R009440 |
| CAS Number | 69123-98-4 |
| Synonyms | 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; Fluoroiodoarauracil; NSC 678514;? |
| Molecular Formula | C9H10FIN2O5 |
| Purity | ≥95% |
| Target | Anti-infection |
| Solubility | Soluble in DMSO |
| Storage | Store at -20°C |
| IUPAC Name | 1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione |
| 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 |
| InChIKey | IPVFGAYTKQKGBM-BYPJNBLXSA-N |
| SMILES | C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)I |
| Reference | </br>1:Review of the Fialuridine (FIAU) Clinical Trials. Institute of Medicine (US) Committee to Review the Fialuridine (FIAU/FIAC) Clinical Trials; Manning FJ, Swartz M, editors. Washington (DC): National Academies Press (US); 1995. PMID: 25121268 Free Books & Documents</br>2:Fialuridine induces acute liver failure in chimeric TK-NOG mice: a model for detecting hepatic drug toxicity prior to human testing. Xu D, Nishimura T, Nishimura S, Zhang H, Zheng M, Guo YY, Masek M, Michie SA, Glenn J, Peltz G.PLoS Med. 2014 Apr 15;11(4):e1001628. doi: 10.1371/journal.pmed.1001628. eCollection 2014 Apr. PMID: 24736310 Free PMC Article</br>3:Identification of the mitochondrial targeting signal of the human equilibrative nucleoside transporter 1 (hENT1): implications for interspecies differences in mitochondrial toxicity of fialuridine. Lee EW, Lai Y, Zhang H, Unadkat JD.J Biol Chem. 2006 Jun 16;281(24):16700-6. Epub 2006 Apr 4. PMID: 16595656 Free Article</br>4:Antiviral activity and toxicity of fialuridine in the woodchuck model of hepatitis B virus infection. Tennant BC, Baldwin BH, Graham LA, Ascenzi MA, Hornbuckle WE, Rowland PH, Tochkov IA, Yeager AE, Erb HN, Colacino JM, Lopez C, Engelhardt JA, Bowsher RR, Richardson FC, Lewis W, Cote PJ, Korba BE, Gerin JL.Hepatology. 1998 Jul;28(1):179-91. PMID: 9657111 </br>5:Mitochondrial injury. Lessons from the fialuridine trial. Honkoop P, Scholte HR, de Man RA, Schalm SW.Drug Saf. 1997 Jul;17(1):1-7. Review. PMID: 9258627 </br>6:Fialuridine toxicity. Schmid R.Hepatology. 1997 Jun;25(6):1548. No abstract available. PMID: 9185783 </br>7:Mitochondrial and cellular toxicity induced by fialuridine in human muscle in vitro. Semino-Mora C, Leon-Monzon M, Dalakas MC.Lab Invest. 1997 Apr;76(4):487-95. PMID: 9111511 </br>8:Fialuridine is phosphorylated and inhibits DNA synthesis in isolated rat hepatic mitochondria. Horn DM, Neeb LA, Colacino JM, Richardson FC.Antiviral Res. 1997 Mar;34(1):71-4. PMID: 9107387 </br>9:Histopathologic changes associated with fialuridine hepatotoxicity. Kleiner DE, Gaffey MJ, Sallie R, Tsokos M, Nichols L, McKenzie R, Straus SE, Hoofnagle JH.Mod Pathol. 1997 Mar;10(3):192-9. PMID: 9071726 </br>10:Depletion of mitochondrial DNA, destruction of mitochondria, and accumulation of lipid droplets result from fialuridine treatment in woodchucks (Marmota monax). Lewis W, Griniuviene B, Tankersley KO, Levine ES, Montione R, Engelman L, de Courten-Myers G, Ascenzi MA, Hornbuckle WE, Gerin JL, Tennant BC.Lab Invest. 1997 Jan;76(1):77-87. PMID: 9010451 |
