Preferred Label : Fosifloxuridine Nafalbenamide;
NCIt synonyms : Nucleotide Analog NUC-3373; 5-FU Analog Prodrug NUC-3373; Phosphoramidate-FUDR-MP Prodrug NUC-3373; L-Alanine, N-(-2'-Deoxy-2',2'-difluoro-p-1-naphthalenyl-5'-cytidylyl)-, Phenylmethyl
Ester;
NCIt definition : A phosphoramidate-based prodrug of the monophosphate (MP) form of 5-fluoro-2'-deoxyuridine
(FUdR; FUDR), the active metabolite of fluorouracil (5-FU), an antimetabolite fluoropyrimidine
analog of the pyrimidine nucleoside, with potential antineoplastic activity. Upon
administration of the nucleotide analog prodrug fosifloxuridine nafalbenamide, fosifloxuridine
nafalbenamide is readily taken up by tumor cells. In the tumor cell, the phosphoramidate
moiety is removed and fosifloxuridine nafalbenamide is converted to its active form
FUDR-MP. In turn, FUDR-MP binds to and inhibits thymidylate synthase (TS), resulting
in the depletion of thymidine triphosphate (TTP) and thus DNA synthesis. With the
phosphoramidate moiety attached to FUDR-MP, fosifloxuridine nafalbenamide, compared
to 5-FU, is more lipophilic and accumulates in cancer cells by passive diffusion and
does not require a nucleoside transporter, thereby generating higher intracellular
concentrations. In addition, compared to 5-FU, once inside the cell FUDR-MP does not
need to be phosphorylated and is already in its active form. Unlike 5-FU, fosifloxuridine
nafalbenamide does not get deactivated or converted into toxic metabolites by dihydropyrimidine
dehydrogenase (DPD) and thymidine phosphorylase (TP), which leads to both a longer
half-life and less toxicity.;
UNII : 4YO6QT3SZ9;
InChIKey : BIOWRMNRHMERIO-ZVAHOJSLSA-N;
CAS number : 1332837-31-6;
Molecule name : NUC 3373; NUC-3373;
NCI Metathesaurus CUI : CL935731;
Origin ID : C156680;
UMLS CUI : C5139753;
Semantic type(s)
- concept_is_in_subset
- has_target
