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Compound Detail

CHEMBL408513

BELINOSTAT
💊 Approved Drug
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💊 Approved Drug
O=C(/C=C/c1cccc(S(=O)(=O)Nc2ccccc2)c1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL408513
Name BELINOSTAT
Phase Approved
Structure Type MOL
InChI Key NCNRHFGMJRPRSK-MDZDMXLPSA-N
Therapeutic ✓ Yes

Known Names

Beleodaq Belinostat NSC-726630 NSC726630 PX-105684 PXD-101 PXD101
42
Targets
168
Activities
3
Assay Types
24
PK Parameters
20
Publications
7
Known Names
20
Indications
1
Mechanisms

Molecular Properties

318.4
MW (Da)
2.01
ALogP
4
HBA
3
HBD
95.5
PSA (Ų)
0.45
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2014
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -stat
USAN Year 2006

Extended Properties

Molecular Formula C15H14N2O4S
MW 318.35
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -1.01

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Histone deacetylase inhibitor INHIBITOR Histone deacetylase ✓ ✓

Indications

Lymphoma, T-Cell Lymphoma, T-Cell, Peripheral Lymphoma, T-Cell, Peripheral Neoplasms Neoplasms Burkitt Lymphoma Carcinoma Carcinoma, Endometrioid Cystadenoma, Serous Fallopian Tube Neoplasms Glioblastoma Leukemia, Myeloid, Acute Leukemia-Lymphoma, Adult T-Cell Lymphoma, Large B-Cell, Diffuse Lymphoma, Large-Cell, Anaplastic Lymphoma, Mantle-Cell Lymphoma, Non-Hodgkin Lymphoma, T-Cell, Cutaneous Mesothelioma Multiple Myeloma

ATC Classification

L01XH04
belinostat
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 127 meas. best 10.23
Ki 29 meas. best 9.07
EC50 12 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
RAW264.7
CHEMBL612557
 IC50 10.23 6.575 0.1 4
Histone deacetylase 1
CHEMBL325
 Ki 9.07 8.5667 0.8 3
Histone deacetylase 2
CHEMBL1937
 Ki 9.07 8.5933 0.8 3
Histone deacetylase 1
CHEMBL325
 IC50 8.86 7.6767 1.4 12
Histone deacetylase 3
CHEMBL1829
 Ki 8.82 8.4533 1.5 3
Histone deacetylase 6
CHEMBL1865
 Ki 8.8 8.5333 1.6 3
Histone deacetylase 3
CHEMBL1829
 IC50 8.14 7.775 7.3 6
Histone deacetylase 6
CHEMBL1865
 IC50 8.01 7.2721 9.8 14
Histone deacetylase
CHEMBL2093865
 IC50 8.0 7.5757 10.0 7
Histone deacetylase 4
CHEMBL3524
 Ki 7.82 6.8867 15.0 3
Histone deacetylase 4
CHEMBL3524
 IC50 7.82 7.2925 15.0 4
Histone deacetylase 2
CHEMBL1937
 IC50 7.66 7.4667 22.0 6
Histone deacetylase 8
CHEMBL3192
 Ki 7.66 7.62 22.0 3
Histone deacetylase 8
CHEMBL3192
 IC50 7.66 6.696 22.0 10
Histone deacetylase 9
CHEMBL4145
 IC50 7.62 7.49 24.0 2
Histone deacetylase 9
CHEMBL4145
 Ki 7.62 6.94 24.0 3
Histone deacetylase 5
CHEMBL2563
 IC50 7.6 7.36 25.0 2
Histone deacetylase 5
CHEMBL2563
 Ki 7.6 7.04 25.0 3
Histone deacetylase (HDAC1 and HDAC2)
CHEMBL2111429
 IC50 7.6 7.6 25.0 1
Histone deacetylase 11
CHEMBL3310
 Ki 7.57 7.57 27.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 7.57 7.465 27.0 2
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 7.57 7.57 27.0 1
Histone deacetylase 3
CHEMBL1829
 EC50 7.52 7.52 30.0 1
Histone deacetylase
CHEMBL2093865
 EC50 7.52 7.52 30.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 7.51 7.3233 31.0 3
Histone deacetylase 1
CHEMBL325
 EC50 7.39 7.39 41.0 1
Histone deacetylase 7
CHEMBL2716
 Ki 7.29 7.1767 51.0 3
Histone deacetylase 7
CHEMBL2716
 IC50 7.29 6.755 51.0 2
Polyamine deacetylase HDAC10
CHEMBL5103
 Ki 7.23 7.23 59.0 1
Plasmodium falciparum
CHEMBL364
 IC50 7.22 7.154 60.0 5
MDA-MB-231
CHEMBL400
 IC50 7.21 7.21 62.0 1
Histone deacetylase 7
CHEMBL2716
 EC50 7.17 7.17 67.0 1
Jurkat
CHEMBL397
 IC50 7.16 7.16 70.0 1
A549
CHEMBL392
 IC50 7.11 7.11 77.0 1
Unchecked
CHEMBL612545
 IC50 7.09 6.49 81.0 5
Histone deacetylase 6
CHEMBL1865
 EC50 7.09 7.09 82.0 1
HeLa
CHEMBL399
 IC50 7.06 6.44 87.0 3
MCF7
CHEMBL387
 IC50 7.02 7.02 96.0 1
HEL
CHEMBL613888
 IC50 7.0 7.0 100.0 1
Histone deacetylase 4
CHEMBL3524
 EC50 6.94 6.94 115.0 1
Hepatitis C virus
CHEMBL379
 EC50 6.92 6.82 120.0 2
Histone deacetylase 2
CHEMBL1937
 EC50 6.9 6.9 125.0 1
Histone deacetylase 9
CHEMBL4145
 EC50 6.89 6.89 128.0 1
MOLT-4
CHEMBL614177
 IC50 6.85 6.85 140.0 1
HCT-116
CHEMBL394
 IC50 6.8 6.6067 160.0 3
Class 1 histone deacetylase
CHEMBL4523988
 IC50 6.72 6.2875 189.0 4
Histone deacetylase
CHEMBL5541
 IC50 6.67 6.67 214.7 1
Histone deacetylase 8
CHEMBL3192
 EC50 6.67 6.67 216.0 1
THP-1
CHEMBL614245
 IC50 6.4 6.4 400.0 1
U-937
CHEMBL612794
 IC50 6.4 6.4 400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 431.0 ng.hr.mL-1 Mus musculus
AUC 2695.0 ng.hr.mL-1 Homo sapiens
AUC 9993.0 ng.hr.mL-1 Homo sapiens
AUC 47503.0 ng.hr.mL-1 Homo sapiens
CL 193.33 mL.min-1.kg-1 Mus musculus
CL 0.1933 mL.min-1.kg-1 Mus musculus
Cmax 2139.0 nM Homo sapiens
Cmax 100908.0 nM Homo sapiens
Cmax 182924.0 nM Homo sapiens
F 6.66 % Mus musculus
F 6.7 % Mus musculus
F 10.0 % Mus musculus
F 6.7 % Mus musculus
Fu 0.138 - Rattus norvegicus
T1/2 1.21 hr Mus musculus
T1/2 0.3 hr Rattus norvegicus
T1/2 6.75 hr Homo sapiens
T1/2 1.5 hr Homo sapiens
T1/2 0.69 hr Homo sapiens
T1/2 3.49 hr Homo sapiens
T1/2 0.3 hr Rattus norvegicus
Tmax 1.9 hr Homo sapiens
Tmax - hr Homo sapiens
Tmax 0.45 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
RAW264.7 IC50 = 0.059 nM 10.23 Anti-inflammatory activity in LPS-stimulated mouse RAW264.7 cells assessed as su... 25113875
Histone deacetylase 1 Ki = 0.85 nM 9.07 Inhibition of human HDAC1 20139990
Histone deacetylase 2 Ki = 0.85 nM 9.07 Inhibition of human HDAC2 20139990
Histone deacetylase 2 Ki = 0.9 nM 9.05 Inhibition of human HDAC2 25637120
Histone deacetylase 1 Ki = 0.9 nM 9.05 Inhibition of human HDAC1 25637120
Histone deacetylase 1 IC50 = 1.376 nM 8.86 Inhibition of HDAC1 (unknown origin) using Ac-Leu-GlyLys(Ac)-AMC as substrate pr... 30879863
Histone deacetylase 3 Ki = 1.5 nM 8.82 Inhibition of human HDAC3 20139990
Histone deacetylase 3 Ki = 1.5 nM 8.82 Inhibition of human HDAC3 25637120
Histone deacetylase 6 Ki = 1.6 nM 8.8 Inhibition of human HDAC6 20139990
Histone deacetylase 6 Ki = 1.6 nM 8.8 Inhibition of human HDAC6 25637120
Histone deacetylase 3 IC50 = 7.3 nM 8.14 Inhibition of recombinant human FLAG-tagged HDAC3 expressed in human HEK293F cel... 33854701
Histone deacetylase 3 IC50 = 9.0 nM 8.05 Inhibition of recombinant human HDAC3 using Boc-Lys(Ac)-AMC as substrate preincu... 38236416
Histone deacetylase 6 IC50 = 9.85 nM 8.01 Inhibition of recombinant human full length HDAC6 using Fluor-de-Lys as substrat... 28395150
Histone deacetylase 6 Ki = 10.0 nM 8.0 Competitive inhibition of HDAC6 using KI-104 as substrate by fluorescence assay 21634430
Histone deacetylase 6 IC50 = 10.0 nM 8.0 Inhibition of HDAC6 (unknown origin) 37429084
Histone deacetylase 6 IC50 = 10.0 nM 8.0 Inhibition of HDAC6 (unknown origin) 38520762
Histone deacetylase IC50 = 10.0 nM 8.0 Inhibition of HDAC in human HeLa cell extracts 31536895
Histone deacetylase 1 IC50 = 13.0 nM 7.89 Inhibition of recombinant human HDAC1 using Boc-Lys(Ac)-AMC as substrate preincu... 38236416
Histone deacetylase 6 IC50 = 14.0 nM 7.85 Inhibition of recombinant human HDAC6 using Boc-Lys(Ac)-AMC as substrate preincu... 38236416
Histone deacetylase 6 IC50 = 15.0 nM 7.82 Inhibition of HDAC6 (unknown origin) 33035922

Literature References

PubMed DOI Target Context # Activities
32940035 10.1021/acs.jmedchem.0c01541 No relevant target 15
25637120 10.1016/j.bmc.2014.12.066 Homo sapiens 12
29456804 10.1021/acsmedchemlett.7b00504 MCF7 6
27344487 10.1016/j.ejmech.2016.06.023 Unchecked 6
21634430 10.1021/jm2003552 HCT-116 6
33069066 10.1016/j.bmc.2020.115675 Aspartyl/asparaginyl beta-hydroxylase 5
20017493 10.1021/jm901502p Mus musculus 5
21634430 10.1021/jm2003552 Mus musculus 5
28218840 10.1021/acs.jmedchem.6b01507 Leukotriene A-4 hydrolase 5
29374157 10.1038/s41419-017-0120-6 PC-9/ER 5
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
27344487 10.1016/j.ejmech.2016.06.023 NON-PROTEIN TARGET 4
25637120 10.1016/j.bmc.2014.12.066 Trypanosoma brucei brucei 4
29374157 10.1038/s41419-017-0120-6 HCC827ER 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
33691794 10.1186/s13148-021-01037-1 A549 4
31400937 10.1016/j.bmcl.2019.08.002 Class 1 histone deacetylase 4
25113875 10.1016/j.ejmech.2014.08.020 RAW264.7 4
30245402 10.1016/j.ejmech.2018.09.018 Unchecked 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3

Data from ChEMBL 36 via Core Engine