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Thymectacin

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Also known as: 232925-18-7, 2zrz4tsw3f, Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate, Nb-1011, L-alanine, n-(5-((1e)-2-bromoethenyl)-2'-deoxy-p-phenyl-5'-uridylyl)-, methyl ester, Bvdu prodrug

Molecular Formula

C₂₁H₂₅BrN₃O₉P

Molecular Weight

574.3 g/mol

InChI Key

CFBLUORPOFELCE-BACVZHSASA-N

FDA UNII

2ZRZ4TSW3F

Brivudine Phosphoramidate is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVdU) with potential antineoplastic activity. Selectively active against tumor cells expressing high levels of thymidylate synthase (TS), brivudine is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, deoxyuridine monophosphate, for binding to TS. Unlike TS inhibitors, this agent is a reversible substrate for TS catalysis. Thus, TS retains activity and converts BVdUMP into cytotoxic metabolites. As key enzyme in the de novo synthesis of dTMP, TS is an enzyme critical to DNA biosynthesis and is overexpressed in many solid tumors.

1 2D Structure

Thymectacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl (2S)-2-[[[(2R,3S,5R)-5-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate

2.1.2 InChI

InChI=1S/C21H25BrN3O9P/c1-13(20(28)31-2)24-35(30,34-15-6-4-3-5-7-15)32-12-17-16(26)10-18(33-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,24,30)(H,23,27,29)/b9-8+/t13-,16-,17+,18+,35?/m0/s1

2.1.3 InChI Key

CFBLUORPOFELCE-BACVZHSASA-N

2.1.4 Canonical SMILES

CC(C(=O)OC)NP(=O)(OCC1C(CC(O1)N2C=C(C(=O)NC2=O)C=CBr)O)OC3=CC=CC=C3

2.1.5 Isomeric SMILES

C[C@@H](C(=O)OC)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)/C=C/Br)O)OC3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

2ZRZ4TSW3F

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 232925-18-7

2. 2zrz4tsw3f

3. Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate

4. Nb-1011

5. L-alanine, N-(5-((1e)-2-bromoethenyl)-2'-deoxy-p-phenyl-5'-uridylyl)-, Methyl Ester

6. Bvdu Prodrug

7. (2s)-methyl 2-(((((2r,3s,5r)-5-(5-((e)-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

8. Brivudine Phosphoramidate

9. Unii-2zrz4tsw3f

10. Schembl13904642

11. Dtxsid00177862

12. 5-(2-bromovinyl)-2'-deoxy-5'-uridyl-phenyl-alanylphosphoramidate, Trans-

13. Db05116

14. (e)-5-(2-bromovinyl)-2'-deoxy-5'-uridyl Phenyl L-methoxyalaninylphosphoramidate

15. E-5-(2-bromovinyl)-2'-deoxyuridine-5'-(l-methylalaninyl)-phenylphosphoramidate

16. Hy-106168

17. Cs-0025066

18. J3.616.614b

19. Q7799611

20. (s)-2-({(2r,3s,5r)-5-[5-((e)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethoxy}-phenoxy-phosphorylamino)-propionic Acid Methyl Ester

21. Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromovinyl]-2,4-dioxo-pyrimidin-1-yl]-3-hydroxy-tetrahydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate

2.4 Create Date

2006-04-28

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅BrN₃O₉P
Molecular Weight	574.3 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	11
Exact Mass	573.05118 g/mol
Monoisotopic Mass	573.05118 g/mol
Topological Polar Surface Area	153 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	909
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in colorectal cancer.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

NB1011 targets thymidylate synthase (TS), which catalyzes the transformation of E-5-(2-bromovinyl)-2'-deoxyuridine-5'-monophosphate (BVdUMP) into cytotoxic reaction products. Due to the elevated levels of TS expression in tumor cells compared to normal cells, these cytotoxic products are preferentially generated inside tumor cells, and, as expected, NB1011 is more toxic to cells with higher levels of TS expression. Therefore, NB1011 therapy should kill tumor cells without severely damaging normal cells.

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