Fluorodeoxyuridylate information

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
CAS Number	acid: 134-46-3 Na salt: 103226-10-4
3D model (JSmol)	acid: Interactive image Na salt: Interactive image
ChEBI	acid: CHEBI:2129
ChEMBL	acid: ChEMBL886
ChemSpider	acid: 8321
DrugBank	acid: DB03761
KEGG	acid: C04242
PubChem CID	Na salt: 92043924
UNII	acid: 7CJ707H131
CompTox Dashboard (EPA)	acid: DTXSID60158450
InChI 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
Chemical formula	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

Fluorodeoxyuridylate,^[1] 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.

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.^[2]