Fluorodeoxyuridylate

Fluorodeoxyuridylate, also known as FdUMP, 5-fluoro-2'-deoxyuridylate, and  5-fluoro-2'-deoxyuridine 5'-monophosphate, is a molecule formed in vivo from 5-fluorouracil and 5-fluorodeoxyuridine.

Fluorodeoxyuridylate
Names
IUPAC name
2′-Deoxy-5-fluorouridine 5′-(dihydrogen phosphate)
Systematic IUPAC name
[(2R,3S,5R)-5-(5-Fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
FdUMP
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
PubChem CID
UNII
  • InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
    Key: HFEKDTCAMMOLQP-RRKCRQDMSA-N
  • Na salt: InChI=1S/C9H12FN2O8P.Na/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18;/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18);/q;+1/p-1/t5-,6+,7+;/m0./s1
    Key: MMBCLHTXMDSSCH-VWZUFWLJSA-M
SMILES
  • acid: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)F)COP(=O)(O)O)O
  • Na salt: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)F)COP(=O)(O)[O-])O.[Na+]
Properties
C9H11FN2NaO8P
Molar mass 348.155 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

FdUMP acts as a suicide inhibitor of thymidylate synthase (TS). By inhibiting the deoxynucleotide biosynthesis, FdUMP stops the rapidly proliferation of fast-growing tumors, and it is therefore widely used as a cancer treatment.

Fluorouracil (5-FU) performs as a substrate during part of the catalytic cycle, and it is only during the synthesis of thymine from uridine, when it is combined with other molecules to form 5-FdUMP to produce an irreversible inhibition of the thymidylate synthase functions. This inhibition leads to an imbalance of the nucleotide grouping, stopping DNA synthesis.

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