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Pracinostat

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Chemistry

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Also known as: 929016-96-6, Sb939, Sb 939, Pracinostat (sb939), Sb-939, Pracinostat [inn]

Molecular Formula

C₂₀H₃₀N₄O₂

Molecular Weight

358.5 g/mol

InChI Key

JHDKZFFAIZKUCU-ZRDIBKRKSA-N

FDA UNII

GPO2JN4UON

Pracinostat is an orally available, small-molecule histone deacetylase (HDAC) inhibitor with potential antineoplastic activity. Pracinostat inhibits HDACs, which may result in the accumulation of highly acetylated histones, followed by the induction of chromatin remodeling; the selective transcription of tumor suppressor genes; the tumor suppressor protein-mediated inhibition of tumor cell division; and, finally, the induction of tumor cell apoptosis. This agent may possess improved metabolic, pharmacokinetic and pharmacological properties compared to other HDAC inhibitors.

1 2D Structure

Pracinostat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-3-[2-butyl-1-[2-(diethylamino)ethyl]benzimidazol-5-yl]-N-hydroxyprop-2-enamide

2.1.2 InChI

InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+

2.1.3 InChI Key

JHDKZFFAIZKUCU-ZRDIBKRKSA-N

2.1.4 Canonical SMILES

CCCCC1=NC2=C(N1CCN(CC)CC)C=CC(=C2)C=CC(=O)NO

2.1.5 Isomeric SMILES

CCCCC1=NC2=C(N1CCN(CC)CC)C=CC(=C2)/C=C/C(=O)NO

2.2 Other Identifiers

2.2.1 UNII

GPO2JN4UON

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(2-butyl-1-(2-diethylaminoethyl)-1h-benzoimidazol-5-yl)-n-hydroxyacrylamide-hydrochloride

2. Sb939 Compound

2.3.2 Depositor-Supplied Synonyms

1. 929016-96-6

2. Sb939

3. Sb 939

4. Pracinostat (sb939)

5. Sb-939

6. Pracinostat [inn]

7. (e)-3-(2-butyl-1-(2-(diethylamino)ethyl)-1h-benzo[d]imidazol-5-yl)-n-hydroxyacrylamide

8. Gpo2jn4uon

9. Chembl1851943

10. 2-propenamide, 3-(2-butyl-1-(2-(diethylamino)ethyl)-1h-benzimidazol-5-yl)-n-hydroxy-, (2e)-

11. Unii-gpo2jn4uon

12. Pracinostatum

13. (2e)-3-[2-butyl-1-[2-(diethylamino)ethyl]-1h-benzimidazol-5-yl]-n-hydroxyacrylamide

14. (2e)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1h-benzimidazol-5-yl}-n-hydroxyacrylamide

15. Sb939,pracinostat

16. Pracinostat(sb939)

17. Sb939 (pracinostat)

18. Pracinostat [who-dd]

19. Mls006011217

20. Schembl833105

21. Gtpl8365

22. Chebi:95071

23. Dtxsid00239196

24. Ex-a351

25. Bcp02073

26. Bdbm50105330

27. Mfcd17215206

28. Nsc758249

29. S1515

30. Zinc43152558

31. Ccg-264903

32. Cs-0567

33. Db05223

34. Nsc-758249

35. (e)-3-[2-butyl-1-[2-(diethylamino)ethyl]benzimidazol-5-yl]-n-hydroxyprop-2-enamide

36. Ncgc00263136-04

37. Ac-33161

38. As-19395

39. Hy-13322

40. Smr004702979

41. Sw219429-1

42. Ec-000.2481

43. A850037

44. Q18344027

45. Kaempferol 3-o-.beta.-d-(6-e-p-coumaroylglucoside)

46. (2e)-3-[2-butyl-1-[2-(diethylamino)ethyl]-1h-benzimidazol-5-yl]-n-hydroxy-2-propenamide

47. (e)-3-[2-butyl-1-(2-diethylaminoethyl)benzimidazol-5-yl]prop-2-enehydroxamic Acid

48. (2e)-3-(2-butyl-1-(2-(dimethylamino)ethyl)-1h-benzimidazol-5-yl)-n-hydroxyprop-2-enamide

49. (2e)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1h-1,3-benzodiazol-5-yl}-n-hydroxyprop-2-enamide

50. (e)-3-(2-butyl-1-(2-diethylaminoethyl)-1h-benzimidazol-5-yl)-n-hydroxy-2-propenamide

2.4 Create Date

2011-02-14

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₀N₄O₂
Molecular Weight	358.5 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	10
Exact Mass	358.23687621 g/mol
Monoisotopic Mass	358.23687621 g/mol
Topological Polar Surface Area	70.4 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	453
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of various forms of cancer.

Treatment of acute myeloid leukaemia

5 Pharmacology and Biochemistry

5.1 Pharmacology

SB939 is a novel compound with superior pharmaceutical, metabolic and pharmacokinetic properties. SB939 has demonstrated excellent in vivo anti-tumour activity in various animal models with dose proportional pharmacodynamic effects. The pharmacokinetics and pharmacodynamic attributes of SB939 explain and differentiate it as the best in class HDAC inhibitor.

5.2 Absorption, Distribution and Excretion

Absorption

Oral bioavailability in mice is 34%.

5.3 Mechanism of Action

Inhibition of HDAC activity allows for the accumulation of acetyl groups on the histone lysine residues resulting in an open chromatin structure and transcriptional activation. In vitro, SB939 causes the accumulation of acetylated histones and induces cell cycle arrest and/or apoptosis of some transformed cells. The mechanism of the antineoplastic effect of SB939 has not been fully characterized.

Drugs in Development