General
Preferred name
IMATINIB
Synonyms
Gleevec, Imatinib mesylate, STI-571 ()
Gleevec ()
Gleevec,STI-571 ()
IMATINIB MESYLATE ()
STI571 ()
CGP057148B ()
ST-1571 ()
STI-571 ()
CGP-57148B ()
ST-1571 Mesylate ()
Glivec ()
CGP 57148 ()
4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-phenyl]benzamide ()
Imatinib (Mesylate) ()
GLAMOX ()
NSC-743414 ()
NSC-759854 ()
IMATINIB ()
STI571 (Mesylate) ()
CGP-57148B (Mesylate) ()
Imatinib (STI571) Mesylate ()
Imatinib (STI571) ()
Gleevec, Glivec, CGP-57148B,STI571 ()
STI571,Gleevec, Glivec, CGP057148B ()
Imatinib methane sulfonate ()
Imatinib methanesulfonate ()
Imatinib (as mesilate) ()
NSC-716051 ()
QTI571 ()
Imatinib medac ()
QTI-571 ()
Imatinib mesilate ()
Imatinib accord ()
STI 571 ()
?Imatinib-d3 ()
P&D ID
PD001319
CAS
152459-95-5
220127-57-1
1080014-82-9
1134803-18-1
Tags
probe
natural product
drug
available
Approved by
EMA
FDA
First approval
2001
Drug Status
approved
Drug indication
Severe acute respiratory syndrome (SARS)
Lung cancer
Intestinal cancer
Chronic myelogenous leukaemia
Systemic mastocytosis
Acute lymphoblastic leukaemia
Middle East Respiratory Syndrome (MERS)
Max Phase
Phase 4
Probe info
Probe type
calculated probe
experimental probe
Probe sources
Chemical Probes.org
Tool Compound Set
Probe targets
[[ compound.targets[t].gene_name ]]
Probe control
Probe control not defined
Orthogonal probes
57
No orthogonal probes found
Similar probes
10
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Imatinib is an antineoplastic agent and a 2-phenylaminopyrimidine derivative that is used to treat chronic myelogenous leukemia. It works as a specific inhibitor of a number of tyrosine kinase enzymes. Chronic myelogenous leukemia is associated with the Philadelphia chromosome promoting the generation of BCR-ABL mutation, which results from the combination of two genes, known as BCR and ABL. BCR-ABL generates a fusion protein that acts as a constitutively active tyrosine kinase and imatinib works to inhibit this constitutive enzymatic activity.
TOXICITY
The most frequently reported adverse reactions (>30%) were edema, nausea,; vomiting, muscle cramps, musculoskeletal pain, diarrhea, rash, fatigue and; abdominal pain.
COMMENT
Imatinib is a non-selective kinase inhibitor originally developed as a tyrosine kinase inhibitor, as shown in several papers (Nature Biotechnology 23, 329 - 336 (2005) ; Nature Biotechnology 26, 127 - 132 (2008) ). Imatinib is a potent inhibitior of ABL (Kis in the 10s of nM), DDR1 (Ki=0.8 nM), DDR2 (Ki=15 nM), KIT (Ki=14 nM), LCK (K=40 nM), PDGFRB (Ki=14 nM), PDGFRA (Ki=30 nM) and has affinity for many other kinases (see http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=screens...). Imatinib also has high affinity for the human quinone reductase 2 (NQO2) (Ki=80 nM; BMC Struct Biol. 2009; 9: 7). Jun 12 2016 - 1:44pm; This compound has inadequate selectivity to be considered a probe. Jun 12 2016 - 1:44pm
DESCRIPTION
Imatinib is a Type-2 kinase inhibitor. Its main inhibitory activity is against ABL kinase, but it has significant action at secondary targets including platelet-derived growth factor receptor (PDGFR) and stem cell growth factor receptor (KIT).
Coronavirus: imatinib is reported to block Spike protein-induced SARS-CoV and MERS-CoV fusion in vitro , potentially by blocking Abl2 at the endosomal membrane and disrupting the actin dynamics that are required for virus-host fusion . It will be informative to determine if this holds true for SARS-CoV-2, and whether re-purposing of imatinib and/or newer Abl kinase inhibitors (, , , ) could be a viable strategy against COVID-19. This approach would likely to be most effective during the early stage of infection. (GtoPdb)
Coronavirus: imatinib is reported to block Spike protein-induced SARS-CoV and MERS-CoV fusion in vitro , potentially by blocking Abl2 at the endosomal membrane and disrupting the actin dynamics that are required for virus-host fusion . It will be informative to determine if this holds true for SARS-CoV-2, and whether re-purposing of imatinib and/or newer Abl kinase inhibitors (, , , ) could be a viable strategy against COVID-19. This approach would likely to be most effective during the early stage of infection. (GtoPdb)
MOA
ATP-competitive inhibitor
(Chemical Probes.org)
DESCRIPTION
For the treatment of Philadelphia chromosome positive chronic myeloid leukemia (Ph+ CML), Ph+ acute lymphoblastic leukaemia, myelodysplastic/myeloproliferative diseases, aggressive systemic mastocytosis, hypereosinophilic syndrome and/or chronic eosinophilic leukemia (CEL), dermatofibrosarcoma protuberans, and malignant gastrointestinal stromal tumors (GIST).
(PKIDB)
DESCRIPTION
inhibitor of BCR-ABL1 and c-KIT
(Informer Set)
DESCRIPTION
MSK/RSK family kinase inhibitor
(Tocris Bioactive Compound Library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
196
Organisms
4
Compound Sets
45
Axon Medchem Screening Library
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
ChEMBL Drugs
Chemical Probes.org
Clinical kinase drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
Informer Set
Ki Database
Kinase Inhibitors (best-in-class)
LSP-MoA library (Laboratory of Systems Pharmacology)
LSP-OptimalKinase library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
NIH Approved Oncology Drugs
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Pandemic Response Box
PKIDB
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
Tool Compound Set
Welcome Trust Cancer Drugs
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
80
Molecular Weight
493.26
Hydrogen Bond Acceptors
7
Hydrogen Bond Donors
2
Rotatable Bonds
7
Ring Count
5
Aromatic Ring Count
4
cLogP
4.59
TPSA
86.28
Fraction CSP3
0.24
Chiral centers
0.0
Largest ring
6.0
QED
0.39
Structural alerts
2
aggregator (Aggregator Advisor)
Aggregators
aggregator (ZINC)
Aggregators
Related compounds
Custom attributes
(extracted from source data)
Target
ABL1
BCR
KIT
ABL, KIT, PDGFR
Platelet-derived growth factor receptor beta
Stem cell growth factor receptor
Tyrosine-protein kinase ABL
v-Abl
c-Kit
PDGFR
ABL1, PDGFRA, PDGFRB, KIT
ABL1, CSF1R, DDR1, KIT, NTRK1, PDGFRA, PDGFRB, RET
Bcr-Abl inhibitor
BCR-ABL, PDGFR, KIT
RET
NTRK1
CSF1R
PDGFRA
DDR1
PDGFRB
SARS-CoV
Autophagy,Bcr-Abl,c-Kit,PDGFR
ABL1, KIT
Compound status
FDA
Pathway
ABL signaling
Angiogenesis
Tyrosine Kinase/Adaptors
Cytoskeletal Signaling
Chromatin/Epigenetic
Anti-infection
Autophagy
Protein Tyrosine Kinase/RTK
Known off targets
PDGFR, v-Abl
Kinase group
TK
MOA
receptor protein-tyrosine kinase inhibitor
Bcr-Abl
Inhibitor
Abl Kinase Inhibitors
Bcr-Abl Kinase Inhibitors
Inhibitors of Signal Transduction Pathways
Bcr-Abl kinase inhibitor, KIT inhibitor, PDGFR tyrosine kinase receptor inhibitor
Targets
ABL1,KIT,PDGFRA,PDGFRB
Primary Target
Abl Kinase
Member status
virtual
Indication
chronic myeloid leukemia (CML), acute lymphoblastic leukemia (ALL), myelodysplastic diseases (MDS), aggressive systemic mastocytosis (ASM), hypereosinophilic syndrome (HES), chronic eosinophilic leukemia (CEL), dermatofibrosarcoma protuberans (DFSP), gastrointestinal stromal tumors (GIST)
Disease Area
hematologic malignancy, oncology
Target class
Protein kinase
Kinase, Kinase
Orthogonal probe
GNF-5
Therapeutic Class
Antiviral Agents
Anticancer Agents
Target subclass
TK, TK
Source data
