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4 Drugs in Development

4 Drugs in Development

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Also known as: 135598-68-4, Tas-109, Radgocitabine, (2r,3s,4s,5r)-2-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolane-3-carbonitrile, Tas 109, 00m634hd2v

Molecular Formula

C₁₀H₁₂N₄O₄

Molecular Weight

252.23 g/mol

InChI Key

DCYBPMFXJCWXNB-JWIUVKOKSA-N

FDA UNII

00M634HD2V

Radgocitabine is an analogue of the nucleoside deoxycytidine with potential antineoplastic activity. Upon administration, radgocitabine is incorporated into DNA and directly inhibits the activity of DNA polymerase, which may result in inhibition of DNA replication and cell cycle arrest in the S and G2/M phases, DNA fragmentation, and tumor cell apoptosis.

1 2D Structure

Radgocitabine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4S,5R)-2-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolane-3-carbonitrile

2.1.2 InChI

InChI=1S/C10H12N4O4/c11-3-5-8(16)6(4-15)18-9(5)14-2-1-7(12)13-10(14)17/h1-2,5-6,8-9,15-16H,4H2,(H2,12,13,17)/t5-,6+,8-,9+/m0/s1

2.1.3 InChI Key

DCYBPMFXJCWXNB-JWIUVKOKSA-N

2.1.4 Canonical SMILES

C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)C#N

2.1.5 Isomeric SMILES

C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)C#N

2.2 Other Identifiers

2.2.1 UNII

00M634HD2V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2'-cyano-2'-deoxyarabinofuranosylcytosine

2. 2'-cyano-2'deoxy-1-beta-d-arabinofuranosylcytosine

2.3.2 Depositor-Supplied Synonyms

1. 135598-68-4

2. Tas-109

3. Radgocitabine

4. (2r,3s,4s,5r)-2-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolane-3-carbonitrile

5. Tas 109

6. 00m634hd2v

7. 2'-cyano-2'-deoxy-1-(beta-d-arabinofuranosyl)cytosine

8. (2r,3s,4s,5r)-2-(4-amino-2-oxopyrimidin-1(2h)-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-carbonitrile

9. Unii-00m634hd2v

10. Radgocitabine [who-dd]

11. Radgocitabine [inn]

12. Chembl337450

13. Schembl1006241

14. Dtxsid30159474

15. Chebi:145435

16. Dfp10917

17. Ex-a1611

18. Hy-16445a

19. 4-amino-l-(2-cyano-2-deoxy-beta-d-arabinofuranosyl)- 2(1h)-pyrimidinone

20. Akos030573293

21. Cs-6837

22. Db11667

23. Ns00069241

24. A857813

25. 1-(2-deoxy-2-cyano-beta-d-arabinofuranosyl)cytosine

26. Q27231358

27. 1-(2-c-cyano-2-deoxy-beta-d-arabino-pentofuranosyl) Cytosine

28. 2'-c-cyano-2'-deoxy-1-beta-d-arabino-pentofuranosyl-cytosine

29. 2'-cyano-2'-deoxy-1-(.beta.-d-arabinofuranosyl)cytosine

30. 4-amino-1-(2-cyano-2-deoxy-beta-d-arabinofuranosyl)pyrimidin-2(1h)-one

31. 2(1h)-pyrimidinone, 4-amino-1-(2-cyano-2-deoxy-.beta.-d-arabinofuranosyl)-

32. 4-amino-l-(2-cyano-2-deoxy-.beta.-d-arabinofuranosyl)- 2(1h)-pyrimidinone

33. (2r,3s,4s,5r)-2-(4-amino-2-oxopyrimidin-1(2h)-yl)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-3-carbonitrile

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₂N₄O₄
Molecular Weight	252.23 g/mol
XLogP3	-2.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	132
Heavy Atom Count	18
Formal Charge	0
Complexity	466
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1