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Compound Detail

CHEMBL4297674

BRANEBRUTINIB
🧪 Phase II
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🧪 Phase II
CC#CC(=O)N[C@H]1CCCN(c2c(F)cc(C(N)=O)c3[nH]c(C)c(C)c23)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4297674
Name BRANEBRUTINIB
Phase Phase II
Structure Type MOL
InChI Key VJPPLCNBDLZIFG-ZDUSSCGKSA-N

Known Names

Bms-986195 Branebrutinib
10
Targets
34
Activities
3
Assay Types
30
PK Parameters
20
Publications
2
Known Names
3
Indications
1
Mechanisms

Molecular Properties

370.4
MW (Da)
2.13
ALogP
3
HBA
3
HBD
91.2
PSA (Ų)
0.72
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -tinib
USAN Year 2018

Extended Properties

Molecular Formula C20H23FN4O2
MW 370.43
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.85

Mechanism of Action

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

Indications

Arthritis, Rheumatoid Autoimmune Diseases Hematologic Neoplasms

Activity Summary

IC50 27 meas. best 10.4
Kd 6 meas. best 9.25
Ki 1 meas. best 6.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
B cell
CHEMBL5314312
 IC50 10.4 10.4 0.0 1
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 10.05 9.2461 0.1 18
Tyrosine-protein kinase BTK
CHEMBL5251
 Kd 9.25 9.25 0.6 1
Tyrosine-protein kinase Tec
CHEMBL4246
 IC50 9.05 9.005 0.9 2
Tyrosine-protein kinase Tec
CHEMBL4246
 Kd 9.0 9.0 1.0 1
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 IC50 8.82 8.82 1.5 1
Tyrosine-protein kinase TXK
CHEMBL4367
 IC50 8.3 8.3 5.0 1
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 Kd 7.66 7.66 22.0 1
Tyrosine-protein kinase ITK/TSK
CHEMBL2959
 IC50 7.0 7.0 100.0 1
Tyrosine-protein kinase BTK
CHEMBL5251
 Ki 6.94 6.94 116.0 1
Tyrosine-protein kinase ITK/TSK
CHEMBL2959
 Kd 6.5 6.5 320.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 5.98 5.98 1040.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 Kd 5.89 5.89 1300.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 5.7 5.7 2000.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 Kd 5.6 5.6 2500.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.96 4.96 11000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 19262.36 ng.hr.mL-1 Mus musculus
AUC 5186.02 ng.hr.mL-1 Mus musculus
AUC 6667.74 ng.hr.mL-1 Rattus norvegicus
AUC 1815.11 ng.hr.mL-1 Macaca mulatta
AUC 28893.54 ng.hr.mL-1 Canis lupus familiaris
CL 14.0 mL.min-1.kg-1 Mus musculus
CL 8.7 mL.min-1.kg-1 Rattus norvegicus
CL 9.4 mL.min-1.kg-1 Macaca mulatta
CL 0.94 mL.min-1.kg-1 Canis lupus familiaris
Cmax 42000.0 nM Mus musculus
Cmax 7700.0 nM Mus musculus
Cmax 9600.0 nM Rattus norvegicus
Cmax 2300.0 nM Macaca mulatta
Cmax 19000.0 nM Canis lupus familiaris
F 106.0 % Mus musculus
F 74.0 % Rattus norvegicus
F 46.0 % Macaca mulatta
F 81.0 % Canis lupus familiaris
MRT 0.57 hr Mus musculus
MRT 0.8 hr Rattus norvegicus
MRT 1.0 hr Macaca mulatta
MRT 4.1 hr Canis lupus familiaris
T1/2 0.46 hr Mus musculus
T1/2 4.3 hr Rattus norvegicus
T1/2 3.2 hr Macaca mulatta
T1/2 3.0 hr Canis lupus familiaris
Tmax 1.0 hr Mus musculus
Tmax 0.58 hr Rattus norvegicus
Tmax 1.0 hr Macaca mulatta
Tmax 0.67 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
B cell IC50 = 0.04 nM 10.4 Cytotoxicity against human peripheral B cells assessed as reduction in cell viab... 30893553
Tyrosine-protein kinase BTK IC50 = 0.09 nM 10.05 Btk Enzyme Assay: To V-bottom 384-well plates were added test compounds, human r... -
Tyrosine-protein kinase BTK IC50 = 0.09 nM 10.05 Enzyme Assay: To V-bottom 384-well plates were added test compounds, human recom... -
Tyrosine-protein kinase BTK IC50 = 0.09 nM 10.05 Biological Assay: To V-bottom 384-well plates were added test compounds, human r... -
Tyrosine-protein kinase BTK IC50 = 0.1 nM 10.0 Inhibition of recombinant human BTK using fluoresceinated peptide as substrate a... 30893553
Tyrosine-protein kinase BTK IC50 = 0.11 nM 9.96 Btk Enzyme Assay: To V-bottom 384-well plates were added test compounds, human r... -
Tyrosine-protein kinase BTK IC50 = 0.11 nM 9.96 Enzyme Assay: To V-bottom 384-well plates were added test compounds, human recom... -
Tyrosine-protein kinase BTK IC50 = 0.11 nM 9.96 Enzyme Assay: To V-bottom 384-well plates were added test compounds, human recom... -
Tyrosine-protein kinase BTK IC50 = 0.11 nM 9.96 Enzyme Assay: To V-bottom 384-well plates were added test compounds, human recom... -
Tyrosine-protein kinase BTK IC50 = 0.11 nM 9.96 Biological Assay: To V-bottom 384-well plates were added test compounds, human r... -
Tyrosine-protein kinase BTK IC50 = 0.3 nM 9.52 Inhibition of BTK in human peripheral B cells assessed as reduction in CD86 surf... 30893553
Tyrosine-protein kinase BTK IC50 = 0.3 nM 9.52 Inhibition of BTK in human PBMC assessed as reduction in TNFalpha expression 30893553
Tyrosine-protein kinase BTK Kd = 0.56 nM 9.25 Binding affinity to DNA-tagged recombinant BTK (unknown origin) measured after 1... 32083858
Tyrosine-protein kinase BTK IC50 = 0.9 nM 9.05 Inhibition of BTK in human memory B cells assessed as reduction in CD86 surface ... 30893553
Tyrosine-protein kinase Tec IC50 = 0.9 nM 9.05 Inhibition of TEC (unknown origin) 30893553
Tyrosine-protein kinase Tec Kd = 0.99 nM 9.0 Binding affinity to DNA-tagged recombinant TEC (unknown origin) measured after 1... 32083858
Tyrosine-protein kinase Tec IC50 = 1.1 nM 8.96 Inhibition of FLAG-tagged TEC autophosphorylation in HEK293 cells incubated for ... 36912866
Tyrosine-protein kinase BTK IC50 = 1.2 nM 8.92 Inhibition of BTK phosphorylation at Tyr 223 residue in human Ramos cell incubat... 36912866
Cytoplasmic tyrosine-protein kinase BMX IC50 = 1.5 nM 8.82 Inhibition of BMX (unknown origin) 30893553
Tyrosine-protein kinase TXK IC50 = 5.0 nM 8.3 Inhibition of TXK (unknown origin) 30893553

Literature References

PubMed DOI Target Context # Activities
30893553 10.1021/acs.jmedchem.9b00167 ADMET 42
30893553 10.1021/acs.jmedchem.9b00167 Tyrosine-protein kinase BTK 23
30893553 10.1021/acs.jmedchem.9b00167 Mus musculus 19
30893553 10.1021/acs.jmedchem.9b00167 Unchecked 8
32083858 10.1021/acs.jmedchem.9b01916 Unchecked 7
30893553 10.1021/acs.jmedchem.9b00167 No relevant target 6
32083858 10.1021/acs.jmedchem.9b01916 Tyrosine-protein kinase BTK 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
30893553 10.1021/acs.jmedchem.9b00167 Cynomolgus monkey 2
38635563 10.1021/acs.jmedchem.4c00072 ADP-sugar pyrophosphatase 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
36912866 10.1021/acs.jmedchem.2c01938 Unchecked 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
32083858 10.1021/acs.jmedchem.9b01916 Receptor tyrosine-protein kinase erbB-4 1
30893553 10.1021/acs.jmedchem.9b00167 B cell 1
30893553 10.1021/acs.jmedchem.9b00167 Tyrosine-protein kinase Tec 1
32083858 10.1021/acs.jmedchem.9b01916 Receptor tyrosine-protein kinase erbB-2 1
32083858 10.1021/acs.jmedchem.9b01916 Epidermal growth factor receptor 1
30893553 10.1021/acs.jmedchem.9b00167 Tyrosine-protein kinase ITK/TSK 1
32083858 10.1021/acs.jmedchem.9b01916 Tyrosine-protein kinase Tec 1

Data from ChEMBL 36 via Core Engine