Details of the Drug

General Information of Drug (ID: DMTD7AB)

Drug Name
Pracinostat
Synonyms
Pracinostat; 929016-96-6; SB939; SB 939; Pracinostat (SB939); SB-939; UNII-GPO2JN4UON; GPO2JN4UON; CHEMBL1851943; (E)-3-(2-butyl-1-(2-(diethylamino)ethyl)-1H-benzo[d]imidazol-5-yl)-N-hydroxyacrylamide; 2-Propenamide, 3-[2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl]-N-hydroxy-, (2E)-; Pracinostat [INN]; (2E)-3-(2-Butyl-1-[2-(diethylamino)ethyl]-1h-1,3-benzodiazol-5-yl)-n-hydroxyprop-2-enamide; 2-Propenamide, 3-(2-butyl-1-(2-(diethylamino)ethyl)-1H-benzimidazol-5-yl)-N-hydroxy-, (2E)-
Indication
Disease Entry ICD 11 Status REF
Acute myeloid leukaemia 2A60 Phase 3 [1]
Myelodysplastic syndrome 2A37 Phase 2 [2]
Myelofibrosis 2A20.2 Phase 2 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 358.5
Logarithm of the Partition Coefficient (xlogp) 3.1
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Bioavailability
The bioavailability of drug is 30% []
Chemical Identifiers
Formula
C20H30N4O2
IUPAC Name
(E)-3-[2-butyl-1-[2-(diethylamino)ethyl]benzimidazol-5-yl]-N-hydroxyprop-2-enamide
Canonical SMILES
CCCCC1=NC2=C(N1CCN(CC)CC)C=CC(=C2)/C=C/C(=O)NO
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+
InChIKey
JHDKZFFAIZKUCU-ZRDIBKRKSA-N
Cross-matching ID
PubChem CID
49855250
ChEBI ID
CHEBI:95071
CAS Number
929016-96-6
DrugBank ID
DB05223
TTD ID
D0L2UQ
INTEDE ID
DR1832
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histone deacetylase (HDAC) TTBH0VX NOUNIPROTAC Modulator [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
AP-5 complex subunit sigma-1 (AP5S1) OTGS53SC AP5S1_HUMAN Gene/Protein Processing [4]
Bcl-2-modifying factor (BMF) OT90NSLI BMF_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [5]
RWD domain-containing protein 3 (RWDD3) OTE76DY5 RWDD3_HUMAN Gene/Protein Processing [4]
Tumor necrosis factor receptor superfamily member 19 (TNFRSF19) OTTVT4MB TNR19_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 8365).
3 Preclinical metabolism and disposition of SB939 (Pracinostat), an orally active histone deacetylase inhibitor, and prediction of human pharmacokinetics. Drug Metab Dispos. 2011 Dec;39(12):2219-32.
4 Development and validation of the TGx-HDACi transcriptomic biomarker to detect histone deacetylase inhibitors in human TK6 cells. Arch Toxicol. 2021 May;95(5):1631-1645. doi: 10.1007/s00204-021-03014-2. Epub 2021 Mar 26.
5 Discovery of (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl}-N-hydroxyacrylamide (SB939), an orally active histone deacetylase inhibitor with a superior preclinical profile. J Med Chem. 2011 Jul 14;54(13):4694-720. doi: 10.1021/jm2003552. Epub 2011 Jun 16.