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CAS 69123-98-4

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Fialuridine

Description:
Fialuridine, also known by its chemical name 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil, is a nucleoside analog that has garnered interest primarily in the context of antiviral research, particularly for its potential use against hepatitis B virus. It is characterized by the presence of a fluorine atom at the 2' position of the sugar moiety, which alters its biological activity compared to natural nucleosides. Fialuridine exhibits a mechanism of action that involves incorporation into viral RNA or DNA, leading to disruption of viral replication. Its structure allows it to mimic the natural nucleoside uridine, facilitating its uptake by cells. However, Fialuridine has been associated with significant toxicity, particularly hepatotoxicity, which has limited its clinical application. The compound is typically studied in preclinical settings to better understand its pharmacological properties and to explore safer derivatives or formulations. Overall, Fialuridine represents a significant example of how structural modifications in nucleoside analogs can influence their therapeutic potential and safety profiles.
Formula:C9H10FIN2O5
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
InChI key:InChIKey=IPVFGAYTKQKGBM-BYPJNBLXSA-N
SMILES:F[C@@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C(=O)NC(=O)C(I)=C2
Synonyms:
  • 1-(2-Deoxy-2-fluoro-.beta.-D-arabinofuranosyl)-5-iodouracil
  • 1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione
  • 1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodouracil
  • 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione
  • 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodopyrimidine-2,4(1H,3H)-dione
  • 1-(2-Deoxy-2-fluoro-β-<span class="text-smallcaps">D</span>-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione
  • 1-(2-Deoxy-2-fluoro-β-<span class="text-smallcaps">D</span>-arabinofuranosyl)-5-iodouracil
  • 1-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodopyrimidine-2,4(1H,3H)-dione
  • 1-(2-deoxy-2-fluoropentofuranosyl)-5-iodopyrimidine-2,4(1H,3H)-dione
  • 1-[(2R,3S,4R,5R)-3-Fluoro-4-Hydroxy-5-(Hydroxymethyl)Oxolan-2-Yl]-5-Iodopyrimidine-2,4-Dione
  • See more synonyms
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