CAS 13276-67-0

thymidylyl-(3'-5')-2'-deoxy-5-fluorouridine

Description:

Thymidylyl-(3'-5')-2'-deoxy-5-fluorouridine, commonly referred to as 5-fluoro-2'-deoxyuridine monophosphate (FdUMP), is a nucleotide analog that incorporates a fluorine atom at the 5-position of the uracil base. This modification enhances its stability and alters its biological activity. The compound is a key intermediate in the synthesis of various nucleoside analogs and is primarily used in cancer therapy due to its ability to inhibit thymidylate synthase, an enzyme critical for DNA synthesis and repair. As a result, FdUMP can interfere with the proliferation of rapidly dividing cancer cells. The presence of the fluorine atom also contributes to its unique pharmacokinetic properties, making it a valuable tool in the development of chemotherapeutic agents. In terms of solubility, it is generally soluble in aqueous solutions, which facilitates its use in biological studies. Overall, FdUMP exemplifies the strategic modification of nucleotides to enhance therapeutic efficacy in oncology.

Formula: C₁₉H₂₄FN₄O₁₂P

InChI: InChI=1/C19H24FN4O12P/c1-8-4-23(18(29)21-16(8)27)15-3-11(12(6-25)34-15)36-37(31,32)33-7-13-10(26)2-14(35-13)24-5-9(20)17(28)22-19(24)30/h4-5,10-15,25-26H,2-3,6-7H2,1H3,(H,31,32)(H,21,27,29)(H,22,28,30)/t10-,11-,12+,13+,14+,15+/m0/s1

Synonyms:

• Dtpdfu
• Thymidine, 2'-deoxy-5-fluorouridyl-(5'-3')-
• [(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl]methyl (2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl hydrogen phosphate (non-preferred name)
• Thymidylyl-(3'-5')-2'-deoxy-5-fluorouridine