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    Fosifloxuridine Nafalbenamide

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    2D Structure
    Also known as: Nuc-3373, 1332837-31-6, 4yo6qt3sz9, Cpf-373, Nuc-3073, Fosifloxuridine nafalbenamide [usan]
    Molecular Formula
    C29H29FN3O9P
    Molecular Weight
    613.5  g/mol
    InChI Key
    BIOWRMNRHMERIO-ZVAHOJSLSA-N
    FDA UNII
    4YO6QT3SZ9
    Fosifloxuridine Nafalbenamide is 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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    benzyl (2S)-2-[[[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-naphthalen-1-yloxyphosphoryl]amino]propanoate
    2.1.2 InChI
    InChI=1S/C29H29FN3O9P/c1-18(28(36)39-16-19-8-3-2-4-9-19)32-43(38,42-24-13-7-11-20-10-5-6-12-21(20)24)40-17-25-23(34)14-26(41-25)33-15-22(30)27(35)31-29(33)37/h2-13,15,18,23,25-26,34H,14,16-17H2,1H3,(H,32,38)(H,31,35,37)/t18-,23-,25+,26+,43?/m0/s1
    2.1.3 InChI Key
    BIOWRMNRHMERIO-ZVAHOJSLSA-N
    2.1.4 Canonical SMILES
    CC(C(=O)OCC1=CC=CC=C1)NP(=O)(OCC2C(CC(O2)N3C=C(C(=O)NC3=O)F)O)OC4=CC=CC5=CC=CC=C54
    2.1.5 Isomeric SMILES
    C[C@@H](C(=O)OCC1=CC=CC=C1)NP(=O)(OC[C@@H]2[C@H](C[C@@H](O2)N3C=C(C(=O)NC3=O)F)O)OC4=CC=CC5=CC=CC=C54
    2.2 Other Identifiers
    2.2.1 UNII
    4YO6QT3SZ9
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Nuc-3073

    2.3.2 Depositor-Supplied Synonyms

    1. Nuc-3373

    2. 1332837-31-6

    3. 4yo6qt3sz9

    4. Cpf-373

    5. Nuc-3073

    6. Fosifloxuridine Nafalbenamide [usan]

    7. Benzyl (2s)-2-[[[(2r,3s,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-naphthalen-1-yloxyphosphoryl]amino]propanoate

    8. Unii-4yo6qt3sz9

    9. Chembl2181367

    10. Ex-a4413

    11. Who 10749

    12. Db14859

    13. Fosifloxuridine Nafalbenamide [inn]

    14. Hy-109115

    15. Cs-0078080

    16. Fosifloxuridine Nafalbenamide [who-dd]

    17. J3.616.613d

    18. A936616

    19. Benzyl N-[p-ambo-2'-deoxy-5-fluoro-p-(naphthalen-1-yl)-5'-uridyly]}-l-alaninate

    20. L-alanine, N-(2'-deoxy-5-fluoro-p-1-naphthalenyl-5'-uridylyl)-, Phenylmethyl Ester

    21. N-(2'-deoxy-5-fluoro-p-1-naphthalenyl-5'-uridylyl)-l-alanine Phenylmethyl Ester

    22. Benzyl (2s)-2-{[{[(2r,3s,5r)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-1(2h)-pyrimidinyl)-3-hydroxytetrahydro-2-furanyl]methoxy}(1-naphthyloxy)phosphoryl]amino}propanoate

    23. L-alanine, N-(-2'-deoxy-2',2'-difluoro-p-1-naphthalenyl-5'-cytidylyl)-, Phenylmethyl Ester

    2.4 Create Date
    2011-10-03
    3 Chemical and Physical Properties
    Molecular Weight 613.5 g/mol
    Molecular Formula C29H29FN3O9P
    XLogP33
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count12
    Exact Mass613.16254467 g/mol
    Monoisotopic Mass613.16254467 g/mol
    Topological Polar Surface Area153 Ų
    Heavy Atom Count43
    Formal Charge0
    Complexity1100
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1