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Compound Detail

CHEMBL3581647

BIRABRESIB
🧪 Phase II
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🧪 Phase II
Cc1sc2c(c1C)C(c1ccc(Cl)cc1)=N[C@@H](CC(=O)Nc1ccc(O)cc1)c1nnc(C)n1-2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3581647
Name BIRABRESIB
Phase Phase II
Structure Type MOL
InChI Key GNMUEVRJHCWKTO-FQEVSTJZSA-N

Known Names

Birabresib MK-8628 OTX-015 OTX-015 ANHYDROUS OTX015 OTX015 ANHYDROUS Y-803 anhydrous
20
Targets
93
Activities
4
Assay Types
2
PK Parameters
20
Publications
7
Known Names
7
Indications
1
Mechanisms

Molecular Properties

492.0
MW (Da)
5.53
ALogP
7
HBA
2
HBD
92.4
PSA (Ų)
0.37
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -bresib
USAN Year 2016

Extended Properties

Molecular Formula C25H22ClN5O2S
MW 492.00
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -1.20

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bromodomain and extra-terminal motif (BET) inhibitor INHIBITOR Bromodomain and extra-terminal motif (BET) ✓ ✓

Indications

Glioblastoma Breast Neoplasms Carcinoma, Non-Small-Cell Lung Carcinoma, Pancreatic Ductal Leukemia, Myeloid, Acute Lymphoma, Large B-Cell, Diffuse Prostatic Neoplasms, Castration-Resistant

Activity Summary

IC50 66 meas. best 8.52
Ki 22 meas. best 8.4
Kd 4 meas. best 8.46
EC50 1 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bromodomain-containing protein 2
CHEMBL1293289
 IC50 8.52 7.3763 3.0 8
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 8.46 7.925 3.5 4
Bromodomain-containing protein 3
CHEMBL1795186
 Ki 8.4 8.1175 4.0 8
Bromodomain-containing protein 2
CHEMBL1293289
 Ki 8.27 7.9283 5.4 6
Bromodomain-containing protein 4
CHEMBL1163125
 Ki 8.24 8.0125 5.7 8
MM1.S
CHEMBL4296471
 IC50 8.2 7.5667 6.3 3
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 8.05 7.51 9.0 28
MOLM-13
CHEMBL3706572
 IC50 7.96 7.96 11.0 1
Unchecked
CHEMBL612545
 IC50 7.85 7.035 14.0 4
MV4-11
CHEMBL613835
 IC50 7.75 7.36 17.6 4
Bromodomain-containing protein 3
CHEMBL1795186
 IC50 7.68 7.21 21.0 6
THP-1
CHEMBL614245
 IC50 7.48 7.48 33.0 1
D283 Med
CHEMBL614476
 IC50 7.18 7.18 66.0 1
MOLM-14
CHEMBL3706570
 EC50 7.1 7.1 80.0 1
LNCaP
CHEMBL612518
 IC50 6.95 6.95 111.4 1
HD-MB03
CHEMBL5441366
 IC50 6.87 6.87 134.0 1
Kasumi 1
CHEMBL613988
 IC50 6.87 6.87 135.0 1
RS4-11
CHEMBL2366159
 IC50 6.38 6.38 416.0 1
HL-60
CHEMBL383
 IC50 6.09 6.09 820.0 1
TALL-1
CHEMBL2366254
 IC50 5.87 5.87 1350.0 1
HAL-01
CHEMBL2366142
 IC50 5.6 5.6 2530.0 1
K562
CHEMBL385
 IC50 5.55 5.55 2840.0 1
HPBALL
CHEMBL4296435
 IC50 5.15 5.15 7010.0 1
REH
CHEMBL2366320
 IC50 4.82 4.82 15320.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 100.0 hr Homo sapiens
T1/2 1.7 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bromodomain-containing protein 2 IC50 = 3.0 nM 8.52 Inhibition of BRD2 BD2 (unknown origin) by TR-FRET assay 36898329
Bromodomain-containing protein 4 Kd = 3.5 nM 8.46 Binding affinity to BRD4 BD2 domain (unknown origin) 32871345
Bromodomain-containing protein 3 Ki = 4.0 nM 8.4 Displacement of FAM-labeled ZBA248 from BRD3 BD2 (306 to 417 amino acid residues... 26080064
Bromodomain-containing protein 3 Ki = 4.0 nM 8.4 Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged B... 28339196
Bromodomain-containing protein 2 Ki = 5.4 nM 8.27 Displacement of FAM-labeled ZBA248 from BRD2 BD2 (349 to 460 amino acid residues... 26080064
Bromodomain-containing protein 2 Ki = 5.4 nM 8.27 Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged B... 28339196
Bromodomain-containing protein 4 Ki = 5.7 nM 8.24 Binding affinity to human BRD4 BD1 (44 to 168 residues) by fluorescence polariza... 30019901
Bromodomain-containing protein 4 Ki = 6.0 nM 8.22 Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged B... 28339196
Bromodomain-containing protein 4 Ki = 6.0 nM 8.22 Displacement of FAM-labeled ZBA248 from BRD4 BD2 (333 to 460 amino acid residues... 26080064
MM1.S IC50 = 6.3 nM 8.2 Antiproliferative activity against human MM1S cells after 72 hrs by CCK8 or SRB ... 31490070
Bromodomain-containing protein 3 Ki = 7.91 nM 8.1 Binding affinity to recombinant human BRD3 BD1 (24 to 144 residues) assessed as ... 37084596
Bromodomain-containing protein 3 Ki = 8.16 nM 8.09 Binding affinity to recombinant human BRD3 BD2 (306 to 417 residues) assessed as... 37084596
Bromodomain-containing protein 3 Ki = 8.7 nM 8.06 Binding affinity to human recombinant BRD3 BD1 (24 to 144 residues) by fluoresce... 31461688
Bromodomain-containing protein 4 IC50 = 9.0 nM 8.05 Inhibition of BRD4 BD2 (unknown origin) by TR-FRET assay 36898329
Bromodomain-containing protein 4 IC50 = 9.2 nM 8.04 Inhibition of His-tagged BRD4 bromodomain 1 (unknown origin) using [Lys (5,8,12,... 33077265
Bromodomain-containing protein 4 Ki = 9.9 nM 8.0 Binding affinity to human recombinant BRD4 BD2 (333 to 460 residues) by fluoresc... 31461688
Bromodomain-containing protein 2 Ki = 10.3 nM 7.99 Binding affinity to human recombinant BRD2 BD2 (349 to 460 residues) by fluoresc... 31461688
Bromodomain-containing protein 4 IC50 = 10.5 nM 7.98 Inhibition of BRD4 bromodomain 1 (unknown origin) using H4K5Ac/K8Ac/K12Ac/K16Ac ... 39356741
Bromodomain-containing protein 3 Ki = 10.7 nM 7.97 Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged B... 28339196
Bromodomain-containing protein 3 Ki = 10.7 nM 7.97 Displacement of FAM-labeled ZBA248 from BRD3 BD1 (24 to 144 amino acid residues)... 26080064

Literature References

PubMed DOI Target Context # Activities
27607580 10.1038/cddis.2016.271 DV-90 20
27607580 10.1038/cddis.2016.271 A549 20
27607580 10.1038/cddis.2016.271 NCI-H1373 16
27607580 10.1038/cddis.2016.271 NCI-H460 12
31490070 10.1021/acs.jmedchem.9b01094 MV4-11 9
32208600 10.1021/acs.jmedchem.9b01784 Bromodomain-containing protein 4 8
36898329 10.1016/j.ejmech.2023.115246 ADMET 7
31461688 10.1016/j.ejmech.2019.111633 MV4-11 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
33691794 10.1186/s13148-021-01037-1 A549 4
28339196 10.1021/acs.jmedchem.6b01816 Bromodomain-containing protein 2 4
28339196 10.1021/acs.jmedchem.6b01816 Bromodomain-containing protein 3 4
28339196 10.1021/acs.jmedchem.6b01816 Bromodomain-containing protein 4 4
26080064 10.1021/acs.jmedchem.5b00613 Bromodomain-containing protein 4 4
38134745 10.1016/j.ejmech.2023.116052 Bromodomain-containing protein 4 4
35544982 10.1016/j.ejmech.2022.114423 Bromodomain-containing protein 4 3
32208600 10.1021/acs.jmedchem.9b01784 MV4-11 3
31490070 10.1021/acs.jmedchem.9b01094 Bromodomain-containing protein 4 3
31461688 10.1016/j.ejmech.2019.111633 HepG2 3
31461688 10.1016/j.ejmech.2019.111633 Bromodomain-containing protein 3 3

Data from ChEMBL 36 via Core Engine