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CAS 131-06-6

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1-β-D-Arabinofuranosyl-5-fluorouracil

Description:
1-β-D-Arabinofuranosyl-5-fluorouracil, commonly known as Ara-5-FU, is a nucleoside analog of uracil that incorporates a fluorine atom at the 5-position of the pyrimidine ring. This compound is characterized by its structural modification, which includes the arabinofuranosyl sugar moiety, enhancing its biological activity. It exhibits antitumor properties, primarily by interfering with RNA and DNA synthesis, making it a candidate for cancer treatment, particularly in solid tumors. The presence of the fluorine atom contributes to its mechanism of action, as it inhibits thymidylate synthase, an enzyme critical for DNA replication. Ara-5-FU is typically administered in a clinical setting and can be used in combination with other chemotherapeutic agents to improve efficacy. Its pharmacokinetics and metabolism are influenced by the sugar configuration, which affects cellular uptake and retention. Overall, 1-β-D-Arabinofuranosyl-5-fluorouracil represents an important compound in the field of oncology, showcasing the significance of structural modifications in enhancing therapeutic potential.
Formula:C9H11FN2O6
InChI:InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6+,8-/m1/s1
InChI key:InChIKey=FHIDNBAQOFJWCA-MNCSTQPFSA-N
SMILES:O[C@@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C(=O)NC(=O)C(F)=C2
Synonyms:
  • 1-(beta-D-arabinofuranosyl)-5-fluoropyrimidine-2,4(1H,3H)-dione
  • 1-beta-D-Arabinofuranosyl-5-fluoro-(1H,3H)-pyrimidine-2,4-dione
  • 1-β-<span class="text-smallcaps">D</span>-Arabinofuranosyl-5-fluoro-2,4(1H,3H)-pyrimidinedione
  • 1-β-<span class="text-smallcaps">D</span>-Arabinofuranosyl-5-fluorouracil
  • 1-β-<span class="text-smallcaps">D</span>-Arabinosyl-5-fluorouracil
  • 1-β-D-arabinofuranosyl-5-fluoro-(1H,3H)-pyrimidine-2,4-dione
  • 2,4(1H,3H)-Pyrimidinedione, 1-β-<span class="text-smallcaps">D</span>-arabinofuranosyl-5-fluoro-
  • 5-Fluorouracil arabinoside
  • 5-fluoro-1-pentofuranosylpyrimidine-2,4(1H,3H)-dione
  • Nsc 406444
  • See more synonyms
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