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Compound Detail

CHEMBL1642

IMATINIB MESYLATE
💊 Approved Drug
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💊 Approved Drug
CS(=O)(=O)O.Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Nc1nccc(-c2cccnc2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1642
Name IMATINIB MESYLATE
Phase Approved
Structure Type MOL
InChI Key YLMAHDNUQAMNNX-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL941
Active Moiety CHEMBL941

Known Names

Gleevec Glivec Imatinib (as mesilate) Imatinib accord Imatinib actavis Imatinib koanaa Imatinib medac Imatinib mesilate Imatinib mesylate Imatinib methane sulfonate Imatinib methanesulfonate Imatinib teva +7 more
19
Targets
31
Activities
2
Assay Types
18
PK Parameters
20
Publications
19
Known Names
20
Indications
4
Mechanisms

Molecular Properties

493.6
MW (Da)
4.59
ALogP
7
HBA
2
HBD
86.3
PSA (Ų)
0.39
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Stem -tinib

Extended Properties

Molecular Formula C30H35N7O4S
MW 589.72
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness -1.80

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tyrosine-protein kinase ABL inhibitor INHIBITOR Tyrosine-protein kinase ABL1 ✓ ✓
Platelet-derived growth factor receptor beta inhibitor INHIBITOR Platelet-derived growth factor receptor beta ✓ ✓
Stem cell growth factor receptor inhibitor INHIBITOR Mast/stem cell growth factor receptor Kit ✓ ✓
Bcr/Abl fusion protein inhibitor INHIBITOR Bcr/Abl fusion protein ✓ ✓

Indications

Dermatofibrosarcoma Gastrointestinal Stromal Tumors Hypereosinophilic Syndrome Leukemia, Myelogenous, Chronic, BCR-ABL Positive Leukemia, Myelogenous, Chronic, BCR-ABL Positive Myelodysplastic-Myeloproliferative Diseases Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Astrocytoma Glioblastoma Hypertension, Pulmonary Hypertension, Pulmonary Leukemia Leukemia, Biphenotypic, Acute Leukemia, Biphenotypic, Acute Leukemia, Lymphoid Nephrogenic Fibrosing Dermopathy Sarcoma

Activity Summary

IC50 23 meas. best 7.0
EC50 8 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bcr/Abl fusion protein
CHEMBL2096618
 EC50 7.05 7.05 90.0 1
Mast/stem cell growth factor receptor Kit
CHEMBL1936
 IC50 7.0 6.695 100.0 2
LAMA-84
CHEMBL2366090
 IC50 7.0 7.0 100.0 2
KBM5
CHEMBL4483250
 IC50 6.82 6.665 152.2 2
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 6.72 6.545 190.0 2
SGC-7901
CHEMBL614909
 IC50 6.68 6.68 208.0 1
K562
CHEMBL385
 IC50 6.68 6.595 210.0 2
KU812 cell line
CHEMBL613997
 IC50 6.51 6.51 311.2 1
Unchecked
CHEMBL612545
 IC50 6.42 6.42 380.0 1
KU812 cell line
CHEMBL613997
 EC50 6.22 6.22 600.0 1
Platelet-derived growth factor receptor alpha
CHEMBL2007
 EC50 6.17 6.17 680.2 1
MCF7
CHEMBL387
 IC50 6.08 6.08 830.0 1
Mast/stem cell growth factor receptor Kit
CHEMBL1936
 EC50 6.03 6.03 942.9 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.77 5.77 1700.0 1
MDA-MB-231
CHEMBL400
 IC50 5.75 5.75 1800.0 1
A549
CHEMBL392
 IC50 5.73 5.73 1870.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 5.49 5.38 3240.0 2
SARS-CoV
CHEMBL4303836
 EC50 5.01 5.01 9800.0 2
MKN-45
CHEMBL614354
 IC50 4.91 4.91 12180.0 1
Middle East respiratory syndrome-related coronavirus
CHEMBL4296578
 EC50 4.75 4.75 17600.0 2
Platelet-derived growth factor receptor alpha
CHEMBL2007
 IC50 4.7 4.66 20000.0 2
Bel-7402
CHEMBL614279
 IC50 4.26 4.26 55520.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.02 uL/min Homo sapiens
CL 0.06 uL/min Homo sapiens
CL 2.75 uL/min Homo sapiens
CL 0.92 uL/min Homo sapiens
CL 0.05 uL/min Homo sapiens
CL 0.14 uL/min Homo sapiens
CL 0.95 uL/min Homo sapiens
CL 0.07 uL/min Homo sapiens
CL 0.03 uL/min Homo sapiens
Cmax 4456.87 nM Homo sapiens
F 97.0 % Homo sapiens
Fu 0.9 - Homo sapiens
Fu 0.9 - Homo sapiens
Fu 0.8 - Homo sapiens
Fu 0.9 - Homo sapiens
Fu 0.8 - Homo sapiens
Fu 0.8 - Homo sapiens
T1/2 18.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bcr/Abl fusion protein EC50 = 90.0 nM 7.05 Antiproliferative activity against K562 cells expressing Bcr-Abl 16678414
Mast/stem cell growth factor receptor Kit IC50 = 100.0 nM 7.0 Inhibition of c-kit gain of function mutant in human GIST882 cells measured afte... -
LAMA-84 IC50 = 100.0 nM 7.0 Antiproliferative activity against human LAMA-84 cells assessed as cell growth i... 28523104
LAMA-84 IC50 = 100.0 nM 7.0 Antiproliferative activity against human LAMA-84 cells overexpressing BCR/ABL as... 28523104
KBM5 IC50 = 152.2 nM 6.82 Cytotoxicity against Imatinib mesylate sensitive wild-type human KBM5 cells asse... 34052717
Tyrosine-protein kinase ABL1 IC50 = 190.0 nM 6.72 Inhibition of c-Abl (unknown origin) 33539089
K562 IC50 = 210.0 nM 6.68 Cytotoxicity against human K562 cells after 24 hrs by MTT assay 22000207
SGC-7901 IC50 = 208.0 nM 6.68 Antiproliferative activity against human SGC7901 cells assessed as reduction in ... 32866755
KBM5 IC50 = 310.6 nM 6.51 Cytotoxicity against imatinib mesylate resistant wild-type human KBM5 cells expr... 34052717
KU812 cell line IC50 = 311.2 nM 6.51 Cytotoxicity against Bcr-Abl expressing human KU812 cells assessed as cell growt... 34052717
K562 IC50 = 310.0 nM 6.51 Cytotoxicity against human K562 cells measured after 72 hrs by MTT assay 28075592
Unchecked IC50 = 380.0 nM 6.42 Inhibition of PDGFR (unknown origin) 37801827
Mast/stem cell growth factor receptor Kit IC50 = 410.0 nM 6.39 Inhibition of c-Kit (unknown origin) 37801827
Tyrosine-protein kinase ABL1 IC50 = 430.0 nM 6.37 Inhibition of c-ABL 16678414
KU812 cell line EC50 = 600.0 nM 6.22 Cytotoxicity against human KU812 cells assessed as reduction in cell viability a... 29778892
Platelet-derived growth factor receptor alpha EC50 = 680.24 nM 6.17 Inhibition of PDGFRA (unknown origin) autophosphorylation using [gamma32P]ATP me... -
MCF7 IC50 = 830.0 nM 6.08 Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay 22000207
Mast/stem cell growth factor receptor Kit EC50 = 942.9 nM 6.03 Inhibition of c-kit (unknown origin) autophosphorylation using [gamma32P]ATP mea... -
NON-PROTEIN TARGET IC50 = 1700.0 nM 5.77 Growth inhibition of human GIST882 cells expressing c-Kit after 96 hrs by SRB as... 24900212
MDA-MB-231 IC50 = 1800.0 nM 5.75 Cytotoxicity against human MDA-MB-231 cells after 24 hrs by MTT assay 22000207

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 643
30873837 10.1021/acs.jmedchem.8b02007 ADMET 10
23028140 10.1124/dmd.112.048017 Cytochrome P450 3A4 10
30873837 10.1021/acs.jmedchem.8b02007 Unchecked 9
23028140 10.1124/dmd.112.048017 Cytochrome P450 2C8 9
38422699 10.1016/j.ejmech.2024.116251 Tyrosine-protein kinase ABL1 8
23028140 10.1124/dmd.112.048017 Liver microsome 6
23028140 10.1124/dmd.112.048017 Cytochrome P450 3A5 6
22000207 10.1016/j.ejmech.2011.09.039 K562 5
23028140 10.1124/dmd.112.048017 Homo sapiens 4
23028140 10.1124/dmd.112.048017 Cytochrome P450 2D6 4
20014752 10.1021/tx900326k Hepatotoxicity 3
30873837 10.1021/acs.jmedchem.8b02007 Tyrosine-protein kinase ABL1 3
23867390 10.1016/j.bmc.2013.06.040 LAMA-84 3
- 10.1101/2020.03.25.008482 SARS-CoV-2 3
23028140 10.1124/dmd.112.048017 Cytochrome P450 2C9 2
- 10.1101/2020.03.25.008482 ADMET 2
23028140 10.1124/dmd.112.048017 Cytochrome P450 2C19 2
- 10.1101/2020.03.25.008482 Vero C1008 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine