Compound Detail

CHEMBL288441

BOSUTINIB

💊 Approved Drug

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💊 Approved Drug

COc1cc(Nc2c(C#N)cnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c(Cl)cc1Cl

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL288441
Name	BOSUTINIB
Phase	Approved
Structure Type	MOL
InChI Key	UBPYILGKFZZVDX-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Bosutinib SK-606 SKI-606

687

Targets

1,041

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

530.5

MW (Da)

5.19

ALogP

HBA

HBD

82.9

PSA (Å²)

0.38

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2012
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

USAN Stem	-tinib
USAN Year	2005

Extended Properties

Molecular Formula	C26H29Cl2N5O3
MW	530.46
Aromatic Rings	3
Heavy Atoms	36
NP-Likeness	-1.36

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Tyrosine-protein kinase ABL inhibitor	INHIBITOR	Tyrosine-protein kinase ABL1	✓	✓
Tyrosine-protein kinase SRC inhibitor	INHIBITOR	Proto-oncogene tyrosine-protein kinase Src	✓	✓
Tyrosine-protein kinase HCK inhibitor	INHIBITOR	Tyrosine-protein kinase HCK	✓	✓
Tyrosine-protein kinase Lyn inhibitor	INHIBITOR	Tyrosine-protein kinase Lyn	✓	✓

Indications

Leukemia, Myelogenous, Chronic, BCR-ABL Positive Neoplasms Breast Neoplasms Breast Neoplasms Glioblastoma Leukemia Polycystic Kidney, Autosomal Dominant Amyotrophic Lateral Sclerosis Blast Crisis Carcinoma, Non-Small-Cell Lung Cognitive Dysfunction Dementia Mesothelioma Ovarian Neoplasms Pancreatic Neoplasms Peritoneal Neoplasms Thymoma Thymus Neoplasms Urinary Bladder Neoplasms Uterine Cervical Neoplasms

ATC Classification

L01EA04

bosutinib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 728 meas. best 9.52

Kd 307 meas. best 10.54

Ki 5 meas. best 7.9

EC50 1 meas. best 7.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	10.54	9.7394	0.0	17
Mitogen-activated protein kinase kinase kinase kinase 5 CHEMBL4852	IC50	9.52	9.52	0.3	1
Tyrosine-protein kinase Yes CHEMBL2073	IC50	9.4	9.4	0.4	1
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	9.3	7.1179	0.5	14
Tyrosine-protein kinase ABL2 CHEMBL4014	IC50	9.3	9.3	0.5	1
Mitogen-activated protein kinase kinase kinase kinase 5 CHEMBL4852	Kd	9.3	8.55	0.5	2
Tyrosine-protein kinase Lck CHEMBL258	Kd	9.23	8.345	0.6	2
Receptor tyrosine-protein kinase erbB-3 CHEMBL5838	Kd	9.11	9.11	0.8	1
Tyrosine-protein kinase ABL CHEMBL2111414	IC50	9.0	8.98	1.0	2
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	9.0	7.8765	1.0	43
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	Kd	9.0	8.556	1.0	5
Dual specificity mitogen-activated protein kinase kinase 1 CHEMBL3587	IC50	9.0	9.0	1.0	1
Cytoplasmic tyrosine-protein kinase BMX CHEMBL3834	IC50	9.0	8.55	1.0	2
Unchecked CHEMBL612545	IC50	9.0	6.6067	1.0	6
Tyrosine-protein kinase Fgr CHEMBL4454	IC50	8.96	8.96	1.1	1
Molecular identity unknown CHEMBL612546	IC50	8.92	8.92	1.2	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	8.89	8.89	1.3	1
Cyclin-G-associated kinase CHEMBL4355	Kd	8.89	8.5125	1.3	4
Bcr/Abl fusion protein CHEMBL2096618	IC50	8.85	7.97	1.4	3
Tyrosine-protein kinase FRK CHEMBL4223	Kd	8.85	8.21	1.4	2
Tyrosine-protein kinase ABL2 CHEMBL4014	Kd	8.82	8.26	1.5	2
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	8.74	7.1733	1.8	3
Serine/threonine-protein kinase 35 CHEMBL5651	Kd	8.7	8.7	2.0	1
Tyrosine-protein kinase FRK CHEMBL4223	IC50	8.66	8.66	2.2	1
Tyrosine-protein kinase BTK CHEMBL5251	IC50	8.6	8.6	2.5	1
Activated CDC42 kinase 1 CHEMBL4599	IC50	8.57	8.57	2.7	3
Breakpoint cluster region protein CHEMBL5146	Kd	8.52	8.52	3.0	1
Mitogen-activated protein kinase kinase kinase kinase 2 CHEMBL5330	Kd	8.51	7.81	3.1	2
Tyrosine-protein kinase HCK CHEMBL3234	IC50	8.49	8.49	3.2	1
Misshapen-like kinase 1 CHEMBL5518	Kd	8.49	8.49	3.2	1
Tyrosine-protein kinase Blk CHEMBL2250	Kd	8.48	8.48	3.3	1
Tyrosine-protein kinase HCK CHEMBL3234	Kd	8.47	7.9367	3.4	3
KU812 cell line CHEMBL613997	IC50	8.44	7.7367	3.6	3
Serine/threonine-protein kinase 24 CHEMBL5082	IC50	8.41	8.41	3.9	1
Tyrosine-protein kinase Yes CHEMBL2073	Kd	8.4	7.58	4.0	2
Tyrosine-protein kinase Lyn CHEMBL3905	Kd	8.38	7.79	4.2	2
K562 CHEMBL385	IC50	8.37	7.9233	4.3	3
STE20-like serine/threonine-protein kinase CHEMBL4202	Kd	8.33	7.195	4.7	2
Tyrosine-protein kinase BTK CHEMBL5251	Kd	8.32	7.96	4.8	2
Mitogen-activated protein kinase kinase kinase kinase 3 CHEMBL5432	Kd	8.29	7.94	5.1	3
Ephrin type-B receptor 4 CHEMBL5147	IC50	8.26	8.26	5.5	1
Ephrin type-A receptor 3 CHEMBL4954	Kd	8.24	8.24	5.8	1
Tyrosine-protein kinase Fgr CHEMBL4454	Kd	8.2	8.2	6.3	1
Serine/threonine-protein kinase 10 CHEMBL3981	Kd	8.15	7.105	7.0	2
Tyrosine-protein kinase Blk CHEMBL3343	IC50	8.14	8.14	7.3	1
Tyrosine-protein kinase Lyn CHEMBL3905	IC50	8.1	8.1	8.0	2
Dual specificity mitogen-activated protein kinase kinase 5 CHEMBL4948	Kd	8.09	6.935	8.2	2
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Kd	8.09	8.09	8.2	1
Ephrin type-B receptor 2 CHEMBL3290	Kd	8.08	7.335	8.4	2
Ephrin type-B receptor 2 CHEMBL3290	IC50	8.07	8.07	8.5	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	264.0	mL.min-1.g-1	Rattus norvegicus
CL	288.0	mL.min-1.g-1	Homo sapiens
Fu	-	-	Mus musculus
Fu	0.072	-	Rattus norvegicus
Fu	0.045	-	Homo sapiens
T1/2	0.08	hr	Homo sapiens
T1/2	0.08833	hr	Rattus norvegicus
T1/2	0.915	hr	Homo sapiens
T1/2	0.2233	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase ABL1	Kd	=	0.029	nM	10.54	Binding constant for ABL1(F317L)-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.036	nM	10.44	Binding constant for ABL1(Y253F)-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.037	nM	10.43	Binding constant for ABL1(M351T)-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.039	nM	10.41	Binding constant for ABL1(Q252H)-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.047	nM	10.33	Binding constant for ABL1(E255K)-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.057	nM	10.24	Binding constant for ABL1(H396P)-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.057	nM	10.24	Binding constant for ABL1-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.062	nM	10.21	Binding constant for ABL1(H396P)-non phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.086	nM	10.07	Binding constant for ABL1(Q252H)-non phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.1	nM	10.0	Inhibition of ABL (unknown origin)	-
Tyrosine-protein kinase ABL1	Kd	=	0.11	nM	9.96	Binding constant for ABL1(F317L)-non phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.12	nM	9.92	Binding constant for ABL1-non phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.18	nM	9.74	Binding constant for ABL1(F317I)-phosphorylated kinase domain	22037378
Mitogen-activated protein kinase kinase kinase kinase 5	IC50	=	0.3	nM	9.52	Inhibition of MAP4K5	19039322
Tyrosine-protein kinase Yes	IC50	=	0.4	nM	9.4	Inhibition of YES1	19039322
Tyrosine-protein kinase ABL2	IC50	=	0.5	nM	9.3	Inhibition of ABL2	19039322
Mitogen-activated protein kinase kinase kinase kinase 5	Kd	=	0.5	nM	9.3	Binding constant for MAP4K5 kinase domain	22037378
Tyrosine-protein kinase ABL1	IC50	=	0.5	nM	9.3	Inhibition of ABL1	19039322
Tyrosine-protein kinase Lck	Kd	=	0.59	nM	9.23	Binding constant for LCK kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.63	nM	9.2	Binding constant for ABL1(F317I)-non phosphorylated kinase domain	22037378

Literature References

PubMed	DOI	Target Context	# Activities
38116407	10.1021/acsmedchemlett.3c00479	ADMET	18
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
30137981	10.1021/acs.jmedchem.8b01040	Bcr/Abl fusion protein	10
26254279	10.18632/oncotarget.4214	Tyrosine-protein kinase ABL1	9
26254279	10.18632/oncotarget.4214	Proto-oncogene tyrosine-protein kinase Src	9
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
38116407	10.1021/acsmedchemlett.3c00479	Bcr/Abl fusion protein	6
30388464	10.1016/j.ejmech.2018.10.050	Membrane-associated tyrosine- and threonine-specific cdc2-inhibitory kinase	5
19039322	10.1038/leu.2008.334	Mast/stem cell growth factor receptor Kit	5
29191878	10.1126/science.aan4368	Unchecked	5
18485715	10.1016/j.bmc.2008.04.065	HT-29	4
16970400	10.1021/jm060380k	NPM/ALK (Nucleophosmin/ALK tyrosine kinase receptor)	4
16970400	10.1021/jm060380k	BaF3	4
18485715	10.1016/j.bmc.2008.04.065	HepG2	4
29941193	10.1016/j.bmc.2018.06.027	Membrane-associated tyrosine- and threonine-specific cdc2-inhibitory kinase	4
22037378	10.1038/nbt.1990	Proto-oncogene tyrosine-protein kinase receptor Ret	4

Data from ChEMBL 36 via Core Engine