Compound Detail

CHEMBL941

IMATINIB

💊 Approved Drug

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💊 Approved Drug

Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Nc1nccc(-c2cccnc2)n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL941
Name	IMATINIB
Phase	Approved
Structure Type	MOL
InChI Key	KTUFNOKKBVMGRW-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Glamox Imatinib NSC-743414 NSC-759854

231

Targets

1,083

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

493.6

MW (Da)

4.59

ALogP

HBA

HBD

86.3

PSA (Å²)

0.39

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2001
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Stem

-tinib

Extended Properties

Molecular Formula	C29H31N7O
MW	493.62
Aromatic Rings	4
Heavy Atoms	37
NP-Likeness	-1.80

Indications

Gastrointestinal Stromal Tumors Graft vs Host Disease Hypertension, Pulmonary Hypertension, Pulmonary Influenza, Human Leukemia Leukemia, Myelogenous, Chronic, BCR-ABL Positive Leukemia, Myeloid Neoplasms Neoplasms Pneumonia Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Sarcoma Severe Acute Respiratory Syndrome Stroke Arthritis, Rheumatoid Breast Neoplasms Chordoma Colonic Neoplasms

ATC Classification

L01EA01

imatinib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 891 meas. best 10.22

Kd 139 meas. best 9.15

Ki 42 meas. best 7.89

EC50 11 meas. best 7.47

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Receptor tyrosine-protein kinase erbB-2 CHEMBL1824	IC50	10.22	10.22	0.1	1
Epidermal growth factor receptor CHEMBL203	IC50	9.96	9.96	0.1	1
K562 CHEMBL385	IC50	9.82	6.3009	0.1	54
EOL1 CHEMBL614489	IC50	9.7	7.83	0.2	3
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	Kd	9.15	8.765	0.7	4
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	9.0	7.5421	1.0	28
Bcr/Abl fusion protein CHEMBL2096618	IC50	8.96	6.5704	1.1	47
Platelet-derived growth factor receptor alpha CHEMBL2007	IC50	8.7	7.2456	2.0	9
Tyrosine-protein kinase ABL2 CHEMBL4014	Kd	8.22	7.7	6.0	8
Breakpoint cluster region protein CHEMBL5146	Kd	8.15	8.15	7.0	1
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	Kd	8.0	7.8933	10.0	3
Tyrosine-protein kinase ABL1 CHEMBL3099	IC50	7.97	6.27	10.8	3
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	7.9	6.9794	12.6	17
Tyrosine-protein kinase ABL1 CHEMBL1862	Ki	7.89	7.26	13.0	6
TF-1 CHEMBL612552	IC50	7.89	7.89	13.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	7.85	7.75	14.0	3
Bcr/Abl fusion protein CHEMBL2096618	Ki	7.85	7.85	14.0	1
Discoidin domain-containing receptor 2 CHEMBL5122	Kd	7.82	7.46	15.0	3
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	7.79	6.3634	16.4	38
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	7.7	6.3372	19.9	72
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	IC50	7.68	6.5325	21.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.57	5.8097	27.0	74
Carbonic anhydrase 2 CHEMBL205	Ki	7.52	7.52	30.2	1
Molecular identity unknown CHEMBL612546	IC50	7.52	7.125	30.0	2
Mast/stem cell growth factor receptor Kit CHEMBL1936	Ki	7.51	7.51	30.7	1
Platelet-derived growth factor receptor alpha CHEMBL2007	Kd	7.51	7.51	31.0	2
Carbonic anhydrase 1 CHEMBL261	Ki	7.5	7.5	31.9	1
Bcr/Abl fusion protein CHEMBL2096618	EC50	7.47	7.47	34.0	1
Unchecked CHEMBL612545	IC50	7.46	5.8426	34.9	42
BCR/ABL1 CHEMBL4523652	IC50	7.42	6.85	38.0	3
Ribosyldihydronicotinamide dehydrogenase [quinone] CHEMBL3959	Ki	7.41	7.41	39.0	1
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	7.4	7.0533	40.0	3
Tyrosine-protein kinase ABL CHEMBL2111414	IC50	7.4	7.4	40.0	1
Tyrosine-protein kinase Lck CHEMBL258	Kd	7.4	7.3525	39.8	4
Ribosyldihydronicotinamide dehydrogenase [quinone] CHEMBL3959	Kd	7.39	7.39	41.0	1
Ribosyldihydronicotinamide dehydrogenase [quinone] CHEMBL3959	IC50	7.37	6.9533	43.0	3
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	IC50	7.37	6.35	43.0	4
BaF3 CHEMBL614524	IC50	7.32	5.7767	48.0	18
Platelet-derived growth factor receptor beta CHEMBL1913	Ki	7.3	7.3	50.1	1
Platelet-derived growth factor receptor CHEMBL2095189	IC50	7.3	7.0	50.0	3
Platelet-derived growth factor receptor beta CHEMBL2749	IC50	7.3	7.3	50.0	1
KU812 cell line CHEMBL613997	IC50	7.29	7.29	51.3	1
HT-29 CHEMBL384	IC50	7.22	7.22	60.0	2
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	7.14	6.57	72.0	6
LAMA-84 CHEMBL2366090	IC50	7.14	7.14	73.0	1
Carbonic anhydrase 9 CHEMBL3594	Ki	7.12	7.12	75.7	1
Carbonic anhydrase 15 CHEMBL5973	Ki	7.11	7.11	78.0	1
Platelet-derived growth factor receptor alpha CHEMBL2007	EC50	7.05	7.05	90.0	1
MEG-01 CHEMBL2366084	IC50	7.05	7.05	89.2	1
EM-2 CHEMBL2366281	IC50	7.05	7.05	88.8	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	16.73	ng.hr.mL-1	Rattus norvegicus
AUC	702.42	ng.hr.mL-1	Rattus norvegicus
AUC	971.44	ng.hr.mL-1	Rattus norvegicus
AUC	52200.32	ng.hr.mL-1	Homo sapiens
AUC	6647.67	ng.hr.mL-1	Rattus norvegicus
AUC	6462.53	ng.hr.mL-1	Rattus norvegicus
AUC	868.84	ng.hr.mL-1	Rattus norvegicus
AUC	855.6	ng.hr.mL-1	Rattus norvegicus
AUC	781.1	-	Homo sapiens
AUC	24800.0	ng.hr.mL-1	Mus musculus
CL	3.3	mL.min-1.kg-1	Homo sapiens
CL	3.3	mL.min-1.kg-1	Homo sapiens
CL	70.0	%	Homo sapiens
CL	17.0	mL.min-1.kg-1	Rattus norvegicus
CL	66.4	mL.min-1.g-1	Homo sapiens
CL	56.6	mL.min-1.g-1	Rattus norvegicus
CL	18.0	mL.min-1.g-1	Mus musculus
CL	27.88	mL.min-1.kg-1	Rattus norvegicus
CL	19.85	mL.min-1.kg-1	Rattus norvegicus
Cmax	2000.0	nM	Homo sapiens
Cmax	3650.0	nM	Homo sapiens
Cmax	7090.0	nM	Homo sapiens
Cmax	1076.33	nM	Rattus norvegicus
Cmax	1108.14	nM	Rattus norvegicus
Cmax	3.849	nM	Mus musculus
Cmax	2183.87	nM	Mus musculus
Cmax	1865.81	nM	Mus musculus
F	76.51	%	Rattus norvegicus
F	98.3	%	Mus musculus
F	98.3	%	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Receptor tyrosine-protein kinase erbB-2	IC50	=	0.06	nM	10.22	Inhibition of HER2 (unknown origin) incubated for 1 hr in presence of ATP by Kin...	35696863
Epidermal growth factor receptor	IC50	=	0.11	nM	9.96	Inhibition of EGFR (unknown origin) incubated for 1 hr in presence of ATP by Kin...	35696863
K562	IC50	=	0.15	nM	9.82	Antiproliferative activity against human K562 cells after 72 hrs by MTT assay	30605831
EOL1	IC50	=	0.2	nM	9.7	Cytotoxicity against human EOL-1 cells after 72 hrs by alamar-blue cell viabilit...	19301902
EOL1	IC50	=	0.1995	nM	9.7	Cytotoxicity against human EOL-1 cells after 72 hrs by alamar-blue cell viabilit...	19301902
Epithelial discoidin domain-containing receptor 1	Kd	=	0.7	nM	9.15	Binding constant for DDR1 kinase domain	18183025
Epithelial discoidin domain-containing receptor 1	Kd	=	0.7	nM	9.15	Binding constant for DDR1 kinase domain	22037378
Epithelial discoidin domain-containing receptor 1	Kd	=	0.7943	nM	9.1	Binding affinity to DDR1 (unknown origin)	30807144
Tyrosine-protein kinase ABL1	Kd	=	1.0	nM	9.0	Binding affinity to ABL1 (unknown origin)	30807144
Tyrosine-protein kinase ABL1	Kd	=	1.1	nM	8.96	Binding constant for ABL1-non phosphorylated kinase domain	22037378
Bcr/Abl fusion protein	IC50	=	1.1	nM	8.96	Inhibition of wild type Bcr-Abl	20166671
Tyrosine-protein kinase ABL1	Kd	=	1.8	nM	8.74	Binding constant for ABL1(Q252H)-non phosphorylated kinase domain	22037378
Platelet-derived growth factor receptor alpha	IC50	=	1.995	nM	8.7	Inhibition of PDGFRA (unknown origin)	23937569
Tyrosine-protein kinase ABL1	Kd	=	2.2	nM	8.66	Average Binding Constant for ABL1; NA=Not Active at 10 uM	15711537
Tyrosine-protein kinase ABL1	Kd	=	2.5	nM	8.6	Binding constant for ABL1(F317L)-non phosphorylated kinase domain	22037378
Bcr/Abl fusion protein	IC50	=	2.79	nM	8.55	Inhibition of wild type Bcr-Abl (unknown origin) incubated for 1 hr in presence ...	35561654
Platelet-derived growth factor receptor alpha	IC50	=	4.6	nM	8.34	Inhibition of PDGFRalpha (unknown origin) using FAM-labeled peptide as substrate...	28541695
Tyrosine-protein kinase ABL1	Kd	=	5.9	nM	8.23	Binding constant for ABL1(H396P)-non phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL2	Kd	=	6.0	nM	8.22	Binding affinity to human active site of N-terminal hexahistidine-tagged ABL2 ex...	21417343
K562	IC50	=	6.05	nM	8.22	Antiproliferative activity against human imatinib-resistant K562 cells	21376587

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	371
18077425	10.1073/pnas.0707498104	NON-PROTEIN TARGET	206
15930265	10.1158/0008-5472.can-05-0259	Unchecked	82
31158845	10.1038/s41586-019-1291-3	ADMET	60
15930265	10.1158/0008-5472.can-05-0259	Tyrosine-protein kinase ABL1	34
-	10.5281/zenodo.13943903	ADMET	26
27966954	10.1021/acs.jmedchem.6b01290	Mast/stem cell growth factor receptor Kit	26
27545040	10.1021/acs.jmedchem.6b00902	Mast/stem cell growth factor receptor Kit	23
21051535	10.1124/dmd.110.034629	ADMET	21
31250638	10.1021/acs.jmedchem.9b00280	Mast/stem cell growth factor receptor Kit	20
23301703	10.1021/jm301581y	NON-PROTEIN TARGET	20
36728508	10.1021/acs.jmedchem.2c00851	Mast/stem cell growth factor receptor Kit	17
21481795	10.1016/j.ccr.2011.03.003	BaF3	17
29544149	10.1016/j.ejmech.2018.03.003	Rattus norvegicus	17
31046271	10.1021/acs.jmedchem.9b00176	Mast/stem cell growth factor receptor Kit	17
30204441	10.1021/acs.jmedchem.8b00938	Mast/stem cell growth factor receptor Kit	16
23088644	10.1021/jm301188x	NON-PROTEIN TARGET	16
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
21481795	10.1016/j.ccr.2011.03.003	Tyrosine-protein kinase ABL1	15
16415863	10.1038/nchembio760	NON-PROTEIN TARGET	15

Data from ChEMBL 36 via Core Engine