Compound Detail

CHEMBL4072833

EVOBRUTINIB

🧪 Phase III

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🧪 Phase III

C=CC(=O)N1CCC(CNc2ncnc(N)c2-c2ccc(Oc3ccccc3)cc2)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4072833
Name	EVOBRUTINIB
Phase	Phase III
Structure Type	MOL
InChI Key	QUIWHXQETADMGN-UHFFFAOYSA-N

Known Names

Evobrutinib M-2951 M2951 Msc-2364447c Msc2364447c

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

429.5

MW (Da)

4.35

ALogP

HBA

HBD

93.4

PSA (Å²)

0.54

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

USAN Stem	-tinib
USAN Year	2022

Extended Properties

Molecular Formula	C25H27N5O2
MW	429.52
Aromatic Rings	3
Heavy Atoms	32
NP-Likeness	-0.50

Mechanism of Action

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

Indications

Multiple Sclerosis Multiple Sclerosis, Relapsing-Remitting Arthritis, Rheumatoid Lupus Erythematosus, Systemic Kidney Diseases Liver Diseases

Activity Summary

IC50 22 meas. best 8.74

Kd 8 meas. best 8.35

Ki 1 meas. best 5.51

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase BTK CHEMBL5251	IC50	8.74	7.3083	1.8	12
Tyrosine-protein kinase Tec CHEMBL4246	Kd	8.35	8.35	4.5	1
Tyrosine-protein kinase BTK CHEMBL5251	Kd	8.34	8.16	4.6	3
Tyrosine-protein kinase Tec CHEMBL4246	IC50	7.7	7.56	20.0	2
Cytoplasmic tyrosine-protein kinase BMX CHEMBL3834	Kd	7.51	7.51	31.0	1
Receptor tyrosine-protein kinase erbB-4 CHEMBL3009	IC50	7.42	7.42	37.9	1
Cytoplasmic tyrosine-protein kinase BMX CHEMBL3834	IC50	7.42	7.42	37.9	1
TMD8 CHEMBL4296503	IC50	7.25	7.25	56.2	1
Unchecked CHEMBL612545	IC50	7.18	7.18	66.3	1
Early activation antigen CD69 CHEMBL3308911	IC50	5.96	5.96	1100.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	5.51	5.51	3100.0	1
Tyrosine-protein kinase ITK/TSK CHEMBL2959	Kd	5.43	5.43	3700.0	1
Receptor tyrosine-protein kinase erbB-4 CHEMBL3009	Kd	5.25	5.25	5600.0	1
Epidermal growth factor receptor CHEMBL203	IC50	5.24	5.24	5800.0	1
Platelet glycoprotein VI CHEMBL3308912	IC50	5.23	5.23	5840.0	1
Epidermal growth factor receptor CHEMBL203	Kd	5.15	5.15	7100.0	1
ADP-sugar pyrophosphatase CHEMBL4105713	IC50	4.86	4.86	13900.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	110.0	mL.min-1.g-1	Homo sapiens
Cmax	52.0	nM	Mus musculus
F	25.0	%	Mus musculus
F	5.0	%	Rattus norvegicus
T1/2	1.0	hr	Mus musculus
T1/2	1.0	hr	Rattus norvegicus
T1/2	1.0	hr	Canis lupus familiaris
Tmax	0.25	hr	Mus musculus
Tmax	0.25	hr	Rattus norvegicus
Tmax	0.25	hr	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase BTK	IC50	=	1.83	nM	8.74	Inhibition of BTK (unknown origin) measured by ADP-Glo assay	35939993
Tyrosine-protein kinase Tec	Kd	=	4.5	nM	8.35	Binding affinity to DNA-tagged recombinant TEC (unknown origin) measured after 1...	32083858
Tyrosine-protein kinase BTK	Kd	=	4.6	nM	8.34	Binding affinity to wild-type human full length BTK (M1 to S659 residues) expres...	34734694
Tyrosine-protein kinase BTK	Kd	=	4.6	nM	8.34	Inhibition of human full-length wild type BTK (M1 to S659 residues) expressed in...	38712838
Tyrosine-protein kinase BTK	IC50	=	5.0	nM	8.3	Inhibition of human BTK using fluorescein-labeled polyGAT peptide as substrate i...	34734694
Tyrosine-protein kinase BTK	IC50	=	8.9	nM	8.05	Inhibition of BTK (unknown origin)	33773287
Tyrosine-protein kinase BTK	IC50	=	8.9	nM	8.05	Covalent inhibition of N-terminal GST-fused human BTK (2-659(end) amino acids) e...	31368705
Tyrosine-protein kinase BTK	Kd	=	16.0	nM	7.8	Binding affinity to DNA-tagged recombinant BTK (unknown origin) measured after 1...	32083858
Tyrosine-protein kinase BTK	IC50	=	16.9	nM	7.77	Inhibition of BTK (unknown origin) incubated for 140 mins in presence of ATP and...	36462441
Tyrosine-protein kinase Tec	IC50	=	20.0	nM	7.7	Inhibition of FLAG-tagged TEC autophosphorylation in HEK293 cells incubated for ...	36912866
Tyrosine-protein kinase BTK	IC50	=	22.0	nM	7.66	Inhibition of BTK phosphorylation at Tyr 223 residue in human Ramos cell incubat...	36912866
Cytoplasmic tyrosine-protein kinase BMX	Kd	=	31.0	nM	7.51	Binding affinity to DNA-tagged recombinant BMX (unknown origin) measured after 1...	32083858
Cytoplasmic tyrosine-protein kinase BMX	IC50	=	37.9	nM	7.42	Inhibition of cytoplasmic recombinant human full length His-tagged BMX expressed...	29457982
Tyrosine-protein kinase Tec	IC50	=	37.9	nM	7.42	Inhibition of recombinant human cytoplasmic full length His-tagged TEC expressed...	29457982
Receptor tyrosine-protein kinase erbB-4	IC50	=	37.9	nM	7.42	Inhibition of recombinant human cytoplasmic GST-tagged ERBB4 expressed in baculo...	29457982
TMD8	IC50	=	56.2	nM	7.25	Antiproliferative activity against human TMD8 cells incubated for 72 hrs by Cell...	35939993
Tyrosine-protein kinase BTK	IC50	=	62.0	nM	7.21	Inhibition of full-length human recombinant BTK using FITC-Ahx-TSELKKVVALYDYMPMN...	32083858
Tyrosine-protein kinase BTK	IC50	=	61.0	nM	7.21	Inhibition of BTK in vitamin D3 differentiated human THP1 cells assessed as inhi...	32083858
Tyrosine-protein kinase BTK	IC50	=	61.0	nM	7.21	Inhibition of BTK in human PBMC cells assessed as reduction in anti-IgM-stimulat...	31368705
Unchecked	IC50	=	66.3	nM	7.18	Antiinflammatory activity in human PBMC assessed as inhibition of anti-IgM induc...	36462441

Literature References

PubMed	DOI	Target Context	# Activities
31368705	10.1021/acs.jmedchem.9b00794	ADMET	13
31368705	10.1021/acs.jmedchem.9b00794	Mus musculus	13
34734694	10.1021/acs.jmedchem.1c00926	Unchecked	9
38712838	10.1021/acs.jmedchem.4c00220	Unchecked	9
31368705	10.1021/acs.jmedchem.9b00794	Tyrosine-protein kinase BTK	7
32083858	10.1021/acs.jmedchem.9b01916	Unchecked	7
32083858	10.1021/acs.jmedchem.9b01916	Tyrosine-protein kinase BTK	6
34734694	10.1021/acs.jmedchem.1c00926	Tyrosine-protein kinase BTK	3
38635563	10.1021/acs.jmedchem.4c00072	ADP-sugar pyrophosphatase	2
29457982	10.1021/acs.jmedchem.7b01712	Receptor tyrosine-protein kinase erbB-4	2
29457982	10.1021/acs.jmedchem.7b01712	Tyrosine-protein kinase Tec	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
36912866	10.1021/acs.jmedchem.2c01938	Unchecked	2
36462441	10.1016/j.ejmech.2022.114940	Unchecked	2
29457982	10.1021/acs.jmedchem.7b01712	Cytoplasmic tyrosine-protein kinase BMX	2
29457982	10.1021/acs.jmedchem.7b01712	Tyrosine-protein kinase BTK	1
32083858	10.1021/acs.jmedchem.9b01916	Cytoplasmic tyrosine-protein kinase BMX	1
32083858	10.1021/acs.jmedchem.9b01916	Tyrosine-protein kinase Tec	1
29457982	10.1021/acs.jmedchem.7b01712	Receptor tyrosine-protein kinase erbB-2	1

Data from ChEMBL 36 via Core Engine