Please Wait
Applying Filters...
Menu
Xls
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