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Compound Detail

CHEMBL4071161

TIRABRUTINIB
💊 Approved Drug
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💊 Approved Drug
CC#CC(=O)N1CC[C@@H](n2c(=O)n(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4071161
Name TIRABRUTINIB
Phase Approved
Structure Type MOL
InChI Key SEJLPXCPMNSRAM-GOSISDBHSA-N

Known Names

Gs-4059 Ono-4059 ONO-4059(FREE BASE) Tirabrutinib Velexbru
10
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names
7
Indications
1
Mechanisms

Molecular Properties

454.5
MW (Da)
2.75
ALogP
8
HBA
1
HBD
108.3
PSA (Ų)
0.48
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2020
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -tinib
USAN Year 2023

Extended Properties

Molecular Formula C25H22N6O3
MW 454.49
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -0.69

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tyrosine-protein kinase BTK inhibitor INHIBITOR Tyrosine-protein kinase BTK ✓ ✓

Indications

Chronic Urticaria Leukemia, Lymphocytic, Chronic, B-Cell Neoplasms Neoplasms Sjogren's Syndrome Arthritis, Rheumatoid Lymphoma, Non-Hodgkin

ATC Classification

L01EL06
tirabrutinib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 25 meas. best 8.37
Kd 4 meas. best 8.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 IC50 8.37 8.37 4.3 1
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 8.28 6.8536 5.2 11
Tyrosine-protein kinase Tec
CHEMBL4246
 Kd 8.21 8.21 6.2 1
Tyrosine-protein kinase BTK
CHEMBL5251
 Kd 7.85 7.85 14.0 1
Tyrosine-protein kinase Tec
CHEMBL4246
 IC50 7.84 7.475 14.3 2
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 Kd 7.33 7.33 47.0 1
Tyrosine-protein kinase TXK
CHEMBL4367
 IC50 6.94 6.94 116.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 6.43 6.43 375.0 1
Unchecked
CHEMBL612545
 IC50 6.43 6.0633 375.0 3
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 Kd 6.21 6.21 610.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 6.0 6.0 991.0 1
Tyrosine-protein kinase Blk
CHEMBL2250
 IC50 5.95 5.95 1133.0 1
Platelet glycoprotein VI
CHEMBL3308912
 IC50 5.92 5.92 1200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytoplasmic tyrosine-protein kinase BMX IC50 = 4.3 nM 8.37 Inhibition of BMX (unknown origin) 34839996
Tyrosine-protein kinase BTK IC50 = 5.2 nM 8.28 Inhibition of full-length human recombinant BTK using FITC-Ahx-TSELKKVVALYDYMPMN... 32083858
Tyrosine-protein kinase BTK IC50 = 5.6 nM 8.25 Inhibition of BTK (unknown origin) 34839996
Tyrosine-protein kinase Tec Kd = 6.2 nM 8.21 Binding affinity to DNA-tagged recombinant TEC (unknown origin) measured after 1... 32083858
Tyrosine-protein kinase BTK Kd = 14.0 nM 7.85 Binding affinity to DNA-tagged recombinant BTK (unknown origin) measured after 1... 32083858
Tyrosine-protein kinase Tec IC50 = 14.3 nM 7.84 Inhibition of FLAG-tagged TEC autophosphorylation in HEK293 cells incubated for ... 36912866
Tyrosine-protein kinase BTK IC50 = 26.0 nM 7.58 Inhibition of BTK in vitamin D3 differentiated human THP1 cells assessed as inhi... 32083858
Tyrosine-protein kinase BTK IC50 = 29.0 nM 7.54 Inhibition of BTK phosphorylation at Tyr 223 residue in human Ramos cell incubat... 36912866
Cytoplasmic tyrosine-protein kinase BMX Kd = 47.0 nM 7.33 Binding affinity to DNA-tagged recombinant BMX (unknown origin) measured after 1... 32083858
Tyrosine-protein kinase Tec IC50 = 77.0 nM 7.11 Inhibition of TEC (unknown origin) 34839996
Tyrosine-protein kinase BTK IC50 = 103.0 nM 6.99 Inhibition of BTK in human whole blood-derived CD19+ B cells assessed as suppres... 29457982
Tyrosine-protein kinase TXK IC50 = 116.0 nM 6.94 Inhibition of TXK (unknown origin) 34839996
Tyrosine-protein kinase BTK IC50 = 132.0 nM 6.88 Inhibition of BTK in human B cells assessed as reduction in anti-IgM/IL4-stimula... 32083858
Tyrosine-protein kinase BTK IC50 = 312.3 nM 6.5 Inhibition of BTK in human whole blood derived-basophils assessed as suppression... 29457982
Tyrosine-protein kinase BTK IC50 = 363.0 nM 6.44 Inhibition of BTK in human basophils assessed as reduction in anti-IgE mouse IgG... 32083858
Unchecked IC50 = 375.0 nM 6.43 Z'-LYTE Kinase Assay: The measurement of Btk enzyme inhibitory activity was perf... -
Tyrosine-protein kinase Lck IC50 = 375.0 nM 6.43 Z'-LYTE Kinase Assay: The measurement of Btk enzyme inhibitory activity was perf... -
Receptor tyrosine-protein kinase erbB-2 Kd = 610.0 nM 6.21 Binding affinity to DNA-tagged recombinant ERBB2 (unknown origin) measured after... 32083858
Receptor tyrosine-protein kinase erbB-4 IC50 = 991.0 nM 6.0 Inhibition of ERBB4 (unknown origin) 34839996
Unchecked IC50 = 1057.0 nM 5.98 Z'-LYTE Kinase Assay: The measurement of Btk enzyme inhibitory activity was perf... -

Literature References

PubMed DOI Target Context # Activities
32083858 10.1021/acs.jmedchem.9b01916 Unchecked 7
32083858 10.1021/acs.jmedchem.9b01916 Tyrosine-protein kinase BTK 6
29457982 10.1021/acs.jmedchem.7b01712 Tyrosine-protein kinase BTK 3
29457982 10.1021/acs.jmedchem.7b01712 Unchecked 2
36912866 10.1021/acs.jmedchem.2c01938 Unchecked 2
29457982 10.1021/acs.jmedchem.7b01712 Receptor tyrosine-protein kinase erbB-2 1
29457982 10.1021/acs.jmedchem.7b01712 Epidermal growth factor receptor 1
29457982 10.1021/acs.jmedchem.7b01712 Leukocyte tyrosine kinase receptor 1
29457982 10.1021/acs.jmedchem.7b01712 Receptor tyrosine-protein kinase erbB-4 1
29457982 10.1021/acs.jmedchem.7b01712 Tyrosine-protein kinase Tec 1
29457982 10.1021/acs.jmedchem.7b01712 Tyrosine-protein kinase JAK3 1
29457982 10.1021/acs.jmedchem.7b01712 Tyrosine-protein kinase Blk 1
32083858 10.1021/acs.jmedchem.9b01916 Cytoplasmic tyrosine-protein kinase BMX 1
32083858 10.1021/acs.jmedchem.9b01916 Tyrosine-protein kinase Tec 1
32083858 10.1021/acs.jmedchem.9b01916 Tyrosine-protein kinase ITK/TSK 1
32083858 10.1021/acs.jmedchem.9b01916 Epidermal growth factor receptor 1
32083858 10.1021/acs.jmedchem.9b01916 Receptor tyrosine-protein kinase erbB-2 1
32083858 10.1021/acs.jmedchem.9b01916 Receptor tyrosine-protein kinase erbB-4 1
37801827 10.1016/j.ejmech.2023.115835 Tyrosine-protein kinase BTK 1
29457982 10.1021/acs.jmedchem.7b01712 Tyrosine-protein kinase TXK 1

Data from ChEMBL 36 via Core Engine