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Compound Detail

CHEMBL3301625

SPEBRUTINIB
🧪 Phase II
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🧪 Phase II
C=CC(=O)Nc1cccc(Nc2nc(Nc3ccc(OCCOC)cc3)ncc2F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3301625
Name SPEBRUTINIB
Phase Phase II
Structure Type MOL
InChI Key KXBDTLQSDKGAEB-UHFFFAOYSA-N

Known Names

Btk inhibitor cc-292 Espebrutinib Spebrutinib
34
Targets
78
Activities
2
Assay Types
2
PK Parameters
20
Publications
3
Known Names
3
Indications

Molecular Properties

423.4
MW (Da)
4.25
ALogP
7
HBA
3
HBD
97.4
PSA (Ų)
0.33
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Chemical Probe
USAN Stem -tinib
USAN Year 2014

Extended Properties

Molecular Formula C22H22FN5O3
MW 423.45
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.45

Indications

Leukemia, Lymphocytic, Chronic, B-Cell Lymphoma, Follicular Waldenstrom Macroglobulinemia

Activity Summary

IC50 77 meas. best 9.3
Ki 1 meas. best 7.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 9.3 8.22 0.5 21
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 IC50 8.49 7.03 3.2 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.48 5.464 3.3 5
Tyrosine-protein kinase Tec
CHEMBL4246
 IC50 8.21 8.1967 6.2 3
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 8.07 7.165 8.5 4
Tyrosine-protein kinase BTK
CHEMBL5251
 Ki 7.68 7.68 20.7 1
Tyrosine-protein kinase TXK
CHEMBL4367
 IC50 7.66 7.66 22.0 1
Tyrosine-protein kinase ITK/TSK
CHEMBL2959
 IC50 7.26 6.9267 55.0 3
MV4-11
CHEMBL613835
 IC50 6.61 6.61 245.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 6.36 6.36 442.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 6.27 6.27 533.7 1
JeKo-1
CHEMBL4296445
 IC50 5.89 5.86 1300.0 2
MOLT-4
CHEMBL614177
 IC50 5.83 5.83 1463.0 1
A549
CHEMBL392
 IC50 5.7 5.7 1980.0 1
Early activation antigen CD69
CHEMBL3308911
 IC50 5.51 5.51 3100.0 1
NAMALVA
CHEMBL614049
 IC50 5.47 5.47 3420.0 1
Ramos
CHEMBL614629
 IC50 5.41 4.986 3900.0 5
Tyrosine-protein kinase Lyn
CHEMBL3905
 IC50 5.36 5.36 4400.0 2
MCF-10A
CHEMBL614321
 IC50 5.36 5.36 4360.0 1
HEL
CHEMBL613888
 IC50 5.28 5.28 5300.0 1
Jurkat
CHEMBL397
 IC50 5.17 5.17 6700.0 1
K562
CHEMBL385
 IC50 5.13 5.015 7400.0 2
786-0
CHEMBL613102
 IC50 4.83 4.83 14900.0 1
Unchecked
CHEMBL612545
 IC50 4.8 4.8 16000.0 1
HeLa
CHEMBL399
 IC50 4.76 4.76 17400.0 1
Raji
CHEMBL614628
 IC50 4.75 4.616 17600.0 5
HT-29
CHEMBL384
 IC50 4.72 4.72 18900.0 1
KARPAS-299
CHEMBL2366156
 IC50 4.69 4.69 20300.0 1
HEF
CHEMBL614162
 IC50 4.65 4.65 22600.0 1
PC-3
CHEMBL390
 IC50 4.65 4.65 22200.0 1
BJ
CHEMBL614358
 IC50 4.56 4.56 27600.0 1
MCF7
CHEMBL387
 IC50 4.54 4.54 29000.0 1
NCI-H3122
CHEMBL4296475
 IC50 4.49 4.49 32500.0 1
HepG2
CHEMBL395
 IC50 4.47 4.47 33500.0 1
NCI-H1299
CHEMBL612255
 IC50 4.42 4.42 38500.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 31.9 mL.min-1.g-1 Homo sapiens
T1/2 0.7233 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase BTK IC50 = 0.5 nM 9.3 Inhibition of BTK (unknown origin) 33773287
Tyrosine-protein kinase BTK IC50 = 0.6 nM 9.22 Inhibition of recombinant full-length N-terminal His-tagged human BTK expressed ... 29146136
Tyrosine-protein kinase BTK IC50 = 0.6 nM 9.22 Inhibition of recombinant human N-terminal His-tagged BTK expressed in baculovir... 27994736
Tyrosine-protein kinase BTK IC50 = 0.7 nM 9.15 Inhibition of BTK (unknown origin) 29631132
Tyrosine-protein kinase BTK IC50 = 0.7 nM 9.15 Irreversible inhibition of BTK (unknown origin) 34479103
Tyrosine-protein kinase BTK IC50 = 0.72 nM 9.14 Inhibition of human recombinant full-length N-terminal His-tagged BTK expressed ... 27956037
Tyrosine-protein kinase BTK IC50 = 0.72 nM 9.14 Inhibition of N-terminal His-tagged full length human recombinant BTK expressed ... 27912175
Tyrosine-protein kinase BTK IC50 = 0.72 nM 9.14 Inhibition of human recombinant full-length N-terminal His-tagged BTK expressed ... 28432946
Tyrosine-protein kinase BTK IC50 = 1.0 nM 9.0 Inhibition of human BTK using fluorescein-labeled polyGAT peptide as substrate i... 34734694
Tyrosine-protein kinase BTK IC50 = 2.12 nM 8.67 Inhibition of human recombinant full length BTK expressed in baculovirus in Sf9 ... 31395509
Cytoplasmic tyrosine-protein kinase BMX IC50 = 3.2 nM 8.49 Lanthscreen Eu Kinase Binding Assay : Lanthscreen Eu Kinase Binding assay for BM... -
NON-PROTEIN TARGET IC50 = 3.28 nM 8.48 Antiproliferative activity against B cells (unknown origin) 26976214
Tyrosine-protein kinase BTK IC50 = 4.61 nM 8.34 Inhibition of BTK (unknown origin) 26976214
Tyrosine-protein kinase Tec IC50 = 6.2 nM 8.21 Inhibition of TEC (unknown origin) 29631132
Tyrosine-protein kinase Tec IC50 = 6.2 nM 8.21 Inhibition of TEC (unknown origin) 34479103
Tyrosine-protein kinase BTK IC50 = 6.1 nM 8.21 Lanthscreen Eu Kinase Binding Assay : Lanthscreen Eu Kinase Binding assay for BM... -
Tyrosine-protein kinase Tec IC50 = 6.8 nM 8.17 Lanthscreen Eu Kinase Binding Assay : Lanthscreen Eu Kinase Binding assay for BM... -
Tyrosine-protein kinase JAK3 IC50 = 8.5 nM 8.07 Inhibition of recombinant human N-terminal His-tagged JAK3 (795 to 1124 residues... 31843459
Tyrosine-protein kinase BTK IC50 = 9.0 nM 8.05 Inhibition of full length recombinant human N-terminal His tagged BKT expressed ... 28315597
Tyrosine-protein kinase BTK IC50 = 9.8 nM 8.01 Inhibition of recombinant human His-tagged full length BTK expressed in baculovi... 31843459

Literature References

PubMed DOI Target Context # Activities
27912175 10.1016/j.ejmech.2016.11.047 Ramos 8
29146136 10.1016/j.ejmech.2017.10.080 Ramos 6
29457982 10.1021/acs.jmedchem.7b01712 Unchecked 5
28432946 10.1016/j.ejmech.2017.04.037 Ramos 5
35594541 10.1021/acs.jmedchem.2c00030 Tyrosine-protein kinase BTK 5
28315597 10.1016/j.ejmech.2017.03.001 Tyrosine-protein kinase BTK 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
27994736 10.1021/acsmedchemlett.6b00235 Ramos 4
27956037 10.1016/j.bmc.2016.11.054 Ramos 4
31395509 10.1016/j.bmc.2019.07.043 Tyrosine-protein kinase BTK 4
36399923 10.1016/j.ejmech.2022.114913 JeKo-1 3
31843459 10.1016/j.bmc.2019.115236 ADMET 3
27956037 10.1016/j.bmc.2016.11.054 Molecular identity unknown 3
27994736 10.1021/acsmedchemlett.6b00235 Molecular identity unknown 3
34734694 10.1021/acs.jmedchem.1c00926 Tyrosine-protein kinase BTK 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
31395509 10.1016/j.bmc.2019.07.043 Ramos 2
27994736 10.1021/acsmedchemlett.6b00235 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine