Pracinostat

Pracinostat (SB939) is an orally bioavailable, small-molecule histone deacetylase (HDAC) inhibitor based on hydroxamic acid with potential anti-tumor activity characterized by favorable physicochemical, pharmaceutical, and pharmacokinetic properties.

Pracinostat

Names
Preferred IUPAC name (2E)-3-{2-Butyl-1-[2-(diethylamino)ethyl]-1H-1,3-benzimidazol-5-yl}-N-hydroxyprop-2-enamide
Other names Pracinostat
Identifiers
CAS Number	929016-96-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:95071
ChemSpider	25027185
PubChem CID	49855250
UNII	GPO2JN4UON Y
CompTox Dashboard (EPA)	DTXSID00239196
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+ Key: JHDKZFFAIZKUCU-ZRDIBKRKSA-N InChI=1/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+ Key: JHDKZFFAIZKUCU-ZRDIBKRKBK
SMILES CCCCC1=NC2=C(N1CCN(CC)CC)C=CC(=C2)/C=C/C(=O)NO
Properties
Chemical formula	C20H30N4O2
Molar mass	358.486 g·mol−1
Density	1.1±0.1 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Activity

Pracinostat selectively inhibits HDAC class I, II, IV without class III and HDAC6 in class IIb,^[1] but has no effect on other Zn-binding enzymes, receptors, and ion channels. It accumulates in tumor cells and exerts a continuous inhibition to histone deacetylase, resulting in acetylated histones accumulation, chromatin remodeling, tumor suppressor genes transcription, and ultimately, apoptosis of tumor cells.^[2]

Clinical medication

Clinical studies suggests that pracinostat has potential best pharmacokinetic properties when compared to other oral HDAC inhibitors.^[3] In March 2014, pracinostat has granted Orphan Drug for acute myelocytic leukemia (AML) and for the treatment of T-cell lymphoma by the Food and Drug Administration.