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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

Fosifloxuridine Nafalbenamide

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 Formula	C₂₉H₂₉FN₃O₉P
Molecular Weight	613.5 g/mol
XLogP3	3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	12
Exact Mass	613.16254467 g/mol
Monoisotopic Mass	613.16254467 g/mol
Topological Polar Surface Area	153 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	1100
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1