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Compound Detail

CHEMBL4065122

FENEBRUTINIB
🧪 Phase III
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🧪 Phase III
C[C@H]1CN(C2COC2)CCN1c1ccc(Nc2cc(-c3ccnc(N4CCn5c(cc6c5CC(C)(C)C6)C4=O)c3CO)cn(C)c2=O)nc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4065122
Name FENEBRUTINIB
Phase Phase III
Structure Type MOL
InChI Key WNEODWDFDXWOLU-QHCPKHFHSA-N

Known Names

Fenebrutinib G-02599853 G02599853 Gdc-0853 RG-7845 RG7845 RO-7010939 RO7010939
3
Targets
21
Activities
3
Assay Types
17
PK Parameters
20
Publications
8
Known Names
6
Indications
1
Mechanisms

Molecular Properties

664.8
MW (Da)
3.57
ALogP
11
HBA
2
HBD
121.0
PSA (Ų)
0.31
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

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

Extended Properties

Molecular Formula C37H44N8O4
MW 664.81
Aromatic Rings 4
Heavy Atoms 49
NP-Likeness -0.68

Mechanism of Action

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

Indications

Multiple Sclerosis Multiple Sclerosis, Chronic Progressive Arthritis, Rheumatoid Lupus Erythematosus, Systemic Urticaria Autoimmune Diseases

Activity Summary

IC50 13 meas. best 8.92
Ki 7 meas. best 9.05
Kd 1 meas. best 9.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase BTK
CHEMBL5251
 Kd 9.46 9.46 0.3 1
Tyrosine-protein kinase BTK
CHEMBL5251
 Ki 9.05 8.7071 0.9 7
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 8.92 8.3673 1.2 11
Unchecked
CHEMBL612545
 IC50 8.11 8.11 7.8 1
TMD8
CHEMBL4296503
 IC50 7.9 7.9 12.6 1

Pharmacokinetic Data

Parameter Value Units Species
CL 27.4 mL.min-1.kg-1 Rattus norvegicus
CL 9.4 mL.min-1.kg-1 Homo sapiens
CL 7.6 mL.min-1.kg-1 Homo sapiens
CL 9.5 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Rattus norvegicus
CL 22.0 mL.min-1.kg-1 Rattus norvegicus
CL 314.0 mL.min-1.kg-1 Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Canis lupus familiaris
CL 29.0 mL.min-1.kg-1 Canis lupus familiaris
CL 9.3 mL.min-1.kg-1 Homo sapiens
CL 10.0 mL.min-1.kg-1 Rattus norvegicus
CL 21.0 mL.min-1.kg-1 Canis lupus familiaris
F 65.1 % Rattus norvegicus
F 96.0 % Rattus norvegicus
F 130.0 % Canis lupus familiaris
T1/2 2.2 hr Rattus norvegicus
Vd 5.42 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase BTK Kd = 0.35 nM 9.46 Binding affinity to full length BTK (unknown origin) assessed as dissociation co... 37195170
Tyrosine-protein kinase BTK Ki = 0.9 nM 9.05 Inhibition of BTK (unknown origin) 34839996
Tyrosine-protein kinase BTK Ki = 0.91 nM 9.04 Inhibition of human recombinant C-terminal polyhistidine tagged BTK (1 to 659 re... 29457982
Tyrosine-protein kinase BTK IC50 = 1.2 nM 8.92 Inhibition of BTK in human isolated primary B cells assessed as inhibition of an... 29457982
Tyrosine-protein kinase BTK IC50 = 1.3 nM 8.89 Inhibition of BTK in human mononuclear cell-derived monocytes assessed as inhibi... 29457982
Tyrosine-protein kinase BTK Ki = 1.3 nM 8.89 Inhibition of BTK C481R mutant (unknown origin) expressed in HEK293 cells 29457982
Tyrosine-protein kinase BTK IC50 = 1.4 nM 8.85 Inhibition of BTK in human isolated primary B cells assessed as inhibition of CD... 29457982
Tyrosine-protein kinase BTK Ki = 1.6 nM 8.8 Inhibition of BTK C481S mutant (unknown origin) expressed in HEK293 cells 29457982
Tyrosine-protein kinase BTK Ki = 1.6 nM 8.8 Inhibition of BTK C481S mutant (unknown origin) 34839996
Tyrosine-protein kinase BTK IC50 = 2.3 nM 8.64 Inhibition of BTK (unknown origin) 37676858
Tyrosine-protein kinase BTK IC50 = 2.3 nM 8.64 Inhibition of BTK in human whole blood assessed as reduction in autophosphorylat... 32832028
Tyrosine-protein kinase BTK IC50 = 3.1 nM 8.51 Inhibition of anti-IgM-induced BTK phosphorylation at Y233 in human primary B ce... 29457982
Tyrosine-protein kinase BTK Ki = 3.4 nM 8.47 Inhibition of BTK T474M mutant (unknown origin) expressed in HEK293 cells 29457982
Unchecked IC50 = 7.8 nM 8.11 Cytotoxicity against human MINO cells incubated for 48 hrs by celltitre glo 2.0 ... 37195170
Tyrosine-protein kinase BTK IC50 = 8.0 nM 8.1 Inhibition of BTK in human whole blood assessed as reduction in anti-IgM-stimula... 32832028
Tyrosine-protein kinase BTK IC50 = 8.0 nM 8.1 Inhibition of BTK in human whole blood-derived CD19+ B cells assessed as suppres... 29457982
Tyrosine-protein kinase BTK IC50 = 11.0 nM 7.96 Inhibition of anti-IgM-induced BTK phosphorylation at Y233 in human whole blood ... 29457982
Tyrosine-protein kinase BTK IC50 = 12.1 nM 7.92 Inhibition of BTK in HEK293 cells using NanoGlo substrate incubated for 2 hrs by... 37195170
TMD8 IC50 = 12.6 nM 7.9 Cytotoxicity against human TMD8 cells incubated for 48 hrs by celltitre glo 2.0 ... 37195170
Tyrosine-protein kinase BTK Ki = 12.6 nM 7.9 Inhibition of BTK T474I mutant (unknown origin) expressed in HEK293 cells 29457982

Literature References

PubMed DOI Target Context # Activities
29457982 10.1021/acs.jmedchem.7b01712 Rattus norvegicus 29
29457982 10.1021/acs.jmedchem.7b01712 Tyrosine-protein kinase BTK 20
32832028 10.1021/acsmedchemlett.0c00249 ADMET 12
29457982 10.1021/acs.jmedchem.7b01712 Salmonella typhimurium 8
- 10.6019/CHEMBL5303304 Fibroblast 7
29457982 10.1021/acs.jmedchem.7b01712 Unchecked 6
- 10.6019/CHEMBL5303304 U2OS 6
29457982 10.1021/acs.jmedchem.7b01712 No relevant target 3
37195170 10.1021/acs.jmedchem.3c00176 Unchecked 3
32832028 10.1021/acsmedchemlett.0c00249 No relevant target 3
29457982 10.1021/acs.jmedchem.7b01712 Homo sapiens 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
34839996 10.1016/j.ejmech.2021.114009 Tyrosine-protein kinase BTK 2
32832028 10.1021/acsmedchemlett.0c00249 Tyrosine-protein kinase BTK 2
- 10.6019/CHEMBL5303304 HEK-293T 2
37195170 10.1021/acs.jmedchem.3c00176 TMD8 2
29457982 10.1021/acs.jmedchem.7b01712 PBL 2
29457982 10.1021/acs.jmedchem.7b01712 Escherichia coli 2
29457982 10.1021/acs.jmedchem.7b01712 Voltage-dependent L-type calcium channel subunit alpha-1C 2
29457982 10.1021/acs.jmedchem.7b01712 Sodium channel protein type 5 subunit alpha 2

Data from ChEMBL 36 via Core Engine