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Compound Detail

CHEMBL1851943

PRACINOSTAT
🧪 Phase III
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🧪 Phase III
CCCCc1nc2cc(/C=C/C(=O)NO)ccc2n1CCN(CC)CC

Basic Information

ChEMBL ID CHEMBL1851943
Name PRACINOSTAT
Phase Phase III
Structure Type MOL
InChI Key JHDKZFFAIZKUCU-ZRDIBKRKSA-N

Known Names

Pracinostat SB 939 SB-939 Sb939
19
Targets
35
Activities
3
Assay Types
6
PK Parameters
20
Publications
4
Known Names
7
Indications

Molecular Properties

358.5
MW (Da)
3.24
ALogP
5
HBA
2
HBD
70.4
PSA (Ų)
0.39
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -stat

Extended Properties

Molecular Formula C20H30N4O2
MW 358.49
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -1.26

Indications

Leukemia, Myeloid, Acute Myelodysplastic Syndromes Myeloproliferative Disorders Prostatic Neoplasms, Castration-Resistant Sarcoma Neoplasms Neoplasms

Activity Summary

IC50 20 meas. best 7.3
Ki 14 meas. best 7.8
EC50 1 meas. best 5.02

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 2
CHEMBL1937
Ki 7.8 7.685 16.0 2
Histone deacetylase 4
CHEMBL3524
Ki 7.8 7.8 16.0 1
Histone deacetylase 8
CHEMBL3192
Ki 7.8 7.56 16.0 2
Histone deacetylase 1
CHEMBL325
Ki 7.8 7.675 16.0 2
Histone deacetylase 3
CHEMBL1829
Ki 7.72 7.72 19.0 1
Histone deacetylase 5
CHEMBL2563
Ki 7.68 7.68 21.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
Ki 7.64 7.64 23.0 1
Histone deacetylase 9
CHEMBL4145
Ki 7.62 7.62 24.0 1
Histone deacetylase 11
CHEMBL3310
Ki 7.37 7.37 43.0 1
Histone deacetylase 1
CHEMBL325
IC50 7.3 7.3 50.0 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
IC50 7.16 7.16 70.0 1
Plasmodium falciparum
CHEMBL364
IC50 7.1 7.1 80.0 2
Polyamine deacetylase HDAC10
CHEMBL5103
IC50 7.09 6.13 82.0 3
Histone deacetylase 6
CHEMBL1865
IC50 7.03 6.7467 93.0 3
Histone deacetylase 7
CHEMBL2716
Ki 6.97 6.97 107.0 1
Histone deacetylase
CHEMBL2093865
IC50 6.9 6.9 126.0 1
Histone deacetylase 8
CHEMBL3192
IC50 6.85 6.2 140.0 2
Plasmodium berghei
CHEMBL612653
IC50 6.82 6.82 150.0 2
Histone deacetylase 6
CHEMBL1865
Ki 6.61 6.61 247.0 1
Histone deacetylase 2
CHEMBL1937
IC50 6.54 6.54 290.0 1
Histone deacetylase 5
CHEMBL2563
IC50 5.29 5.29 5113.0 1
MCF7
CHEMBL387
IC50 5.27 5.27 5340.0 1
MDA-MB-231
CHEMBL400
IC50 5.27 5.27 5340.0 1
T47D
CHEMBL614361
IC50 5.27 5.27 5340.0 1
Trypanosoma brucei brucei
CHEMBL612851
EC50 5.02 5.02 9549.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1028.0 ng.hr.mL-1 Homo sapiens
Cmax 497.0 nM Homo sapiens
T1/2 6.7 hr Homo sapiens
T1/2 6.0 hr Rattus norvegicus
T1/2 6.0 hr Homo sapiens
Tmax 1.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 4 Ki = 16.0 nM 7.8 Inhibition of human HDAC4 25637120
Histone deacetylase 1 Ki = 16.0 nM 7.8 Inhibition of recombinant human HDAC-1 expressed in baculovirus infected insect ... -
Histone deacetylase 2 Ki = 16.0 nM 7.8 Inhibition of recombinant human HDAC-2 expressed in baculovirus infected insect ... -
Histone deacetylase 8 Ki = 16.0 nM 7.8 Inhibition of recombinant human HDAC-8 expressed in HEK293-F cells using Fluor d... -
Histone deacetylase 3 Ki = 19.0 nM 7.72 Inhibition of human HDAC3 25637120
Histone deacetylase 5 Ki = 21.0 nM 7.68 Inhibition of human HDAC5 25637120
Polyamine deacetylase HDAC10 Ki = 23.0 nM 7.64 Inhibition of human HDAC10 25637120
Histone deacetylase 9 Ki = 24.0 nM 7.62 Inhibition of human HDAC9 25637120
Histone deacetylase 2 Ki = 27.0 nM 7.57 Inhibition of human HDAC2 25637120
Histone deacetylase 1 Ki = 28.0 nM 7.55 Inhibition of human HDAC1 25637120
Histone deacetylase 11 Ki = 43.0 nM 7.37 Inhibition of human HDAC11 25637120
Histone deacetylase 8 Ki = 48.0 nM 7.32 Inhibition of human HDAC8 25637120
Histone deacetylase 1 IC50 = 50.0 nM 7.3 Inhibition of full length recombinant human C-terminal FLAG/His-tagged HDAC1 (1 ... 29360358
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 70.0 nM 7.16 Inhibition of recombinant human C-terminal His-tagged HDAC3 (1 to 428 end residu... 29360358
Plasmodium falciparum IC50 = 80.0 nM 7.1 Antimalarial activity against Plasmodium falciparum infected in human erythrocyt... 28241112
Plasmodium falciparum IC50 = 80.0 nM 7.1 Antimalarial activity against Plasmodium falciparum infected in human erythrocyt... 24904967
Polyamine deacetylase HDAC10 IC50 = 82.0 nM 7.09 Inhibition of N-terminal FLAG-tagged human HDAC10 (2 to 631 residues) expressed ... 29360358
Histone deacetylase 6 IC50 = 93.0 nM 7.03 Inhibition of recombinant human N-terminal GST-tagged HDAC6 expressed in baculov... 29360358
Histone deacetylase 7 Ki = 107.0 nM 6.97 Inhibition of human HDAC7 25637120
Histone deacetylase IC50 = 126.0 nM 6.9 Inhibition of HDAC in human HeLa cell nuclear extracts using Fluor de Lys as sub... 24119555

Literature References

PubMed DOI Target Context # Activities
28218840 10.1021/acs.jmedchem.6b01507 Leukotriene A-4 hydrolase 5
- 10.6019/CHEMBL4808148 Histone deacetylase 6 5
25637120 10.1016/j.bmc.2014.12.066 Homo sapiens 4
33691794 10.1186/s13148-021-01037-1 A549 4
28241112 10.1021/acs.jmedchem.6b01595 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
24119555 10.1016/j.bmcl.2013.09.051 Histone deacetylase 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL5096127 Schistosoma mansoni 2
32791404 10.1016/j.ejmech.2020.112679 MDA-MB-231 2
30964290 10.1021/acs.jmedchem.8b01936 Polyamine deacetylase HDAC10 2
28985084 10.1021/acs.jmedchem.7b01444 Plasma 2
- 10.1039/C1MD00199J Histone deacetylase 8 1
25637120 10.1016/j.bmc.2014.12.066 Histone deacetylase 3 1
- 10.1039/C1MD00199J Histone deacetylase 1 1
- 10.1039/C1MD00199J Histone deacetylase 2 1
24904967 10.1016/j.ejmech.2014.05.050 Unchecked 1
24904967 10.1016/j.ejmech.2014.05.050 ADMET 1
24119555 10.1016/j.bmcl.2013.09.051 HCT-116 1

Data from ChEMBL 36 via Core Engine