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Details

Stereochemistry ACHIRAL
Molecular Formula C29H31N7O
Molecular Weight 493.6027
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMATINIB

SMILES

CN1CCN(CC2=CC=C(C=C2)C(=O)NC3=CC(NC4=NC=CC(=N4)C5=CC=CN=C5)=C(C)C=C3)CC1

InChI

InChIKey=KTUFNOKKBVMGRW-UHFFFAOYSA-N
InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)

HIDE SMILES / InChI

Molecular Formula C29H31N7O
Molecular Weight 493.6027
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Imatinib (GLEEVEC®) is a tyrosine kinase inhibitor and antineoplastic agent that inhibits the BCR-ABL tyrosine kinase, the constitutive abnormal tyrosine kinase created by the Philadelphia chromosome abnormality in chronic myeloid leukaemia (CML). It inhibits proliferation and induces apoptosis in BCR-ABL positive cell lines as well as fresh leukemic cells from Philadelphia chromosome positive CML. Imatinib (GLEEVEC®) inhibits colony formation in assays using ex vivo peripheral blood and bone marrow samples from CML patients. It is also an inhibitor of the receptor tyrosine kinases for platelet-derived growth factor (PDGF) and stem cell factor (SCF), c-kit, and inhibits PDGF- and SCF-mediated cellular events. In vitro, imatinib (GLEEVEC®) inhibits proliferation and induces apoptosis in gastrointestinal stromal tumor (GIST) cells, which express an activating c-kit mutation.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Acute generalized exanthematous pustulosis associated with STI571 in a patient with chronic myeloid leukemia.
2001
Sarcoma.
2001
ST1571, a tyrosine kinase inhibitor for the treatment of chronic myelogenous leukemia: validating the promise of molecularly targeted therapy.
2001 Aug
Targeting protein kinases for tumor therapy.
2001 Aug
PDGF-beta receptor expression in the dorsocaudal brainstem parallels hypoxic ventilatory depression in the developing rat.
2001 Aug
Growth inhibition of dermatofibrosarcoma protuberans tumors by the platelet-derived growth factor receptor antagonist STI571 through induction of apoptosis.
2001 Aug 1
STI571 inactivation of the gastrointestinal stromal tumor c-KIT oncoprotein: biological and clinical implications.
2001 Aug 16
Chronic myelogenous leukemia.
2001 Aug 22-29
Cutaneous reactions to STI571.
2001 Aug 23
[New target-aimed molecular cancer treatment of chronic myeloid leukemia and gastrointestinal stromal tumor].
2001 Aug 27
Bcr-Abl inhibition as a modality of CML therapeutics.
2001 Aug 31
Mechanisms of resistance imatinib (STI571) in preclinical models and in leukemia patients.
2001 Feb
Mechanisms of resistance to imatinib (STI571) and prospects for combination with conventional chemotherapeutic agents.
2001 Feb
Perspectives on the future of chronic myeloid leukemia treatment.
2001 Jul
Implications of imatinib mesylate for hematopoietic stem cell transplantation.
2001 Jul
Interferon-alfa-based treatment of chronic myeloid leukemia and implications of signal transduction inhibition.
2001 Jul
Molecular studies in chronic myeloid leukemia patients treated with tyrosine kinase inhibitors.
2001 Jul
Signal transduction inhibition: results from phase I clinical trials in chronic myeloid leukemia.
2001 Jul
The role of Bcr-Abl in chronic myeloid leukemia and stem cell biology.
2001 Jul
Implications of signal transduction inhibition for the treatment of chronic myeloid leukemia.
2001 Jul
Cancer treatment. New drugs, new hope.
2001 Jul
Clinical trials referral resource. ST1571.
2001 Jul
[STI571 and gastro intestinal stromal tumors].
2001 Jul
[Anti-tyrosine kinase: the beginning of molecular therapies of cancer and initial results].
2001 Jul
[Leukemogenesis and new therapy development: the example of chronic myelogenous leukemia].
2001 Jul
Chronic myelogenous leukaemia--new therapeutic principles.
2001 Jul
New drug targets genetic malfunction in chronic myeloid leukemia.
2001 Jul 15
New-age drug meets resistance.
2001 Jul 19
Current treatment approaches for chronic myelogenous leukemia.
2001 Jul-Aug
Tyrosine kinase inhibitor STI571 enhances thyroid cancer cell motile response to Hepatocyte Growth Factor.
2001 Jun 28
Recent success with the tyrosine kinase inhibitor STI-571--lessons for targeted therapy of cancer.
2001 Mar
Progenitor cells from patients with advanced phase chronic myeloid leukaemia respond to STI571 in vitro and in vivo.
2001 Nov
STI571: a magic bullet?
2001 Oct
Chronic myeloid leukemia: current treatment options.
2001 Oct 1
Gleevec (STI571) influences metabolic enzyme activities and glucose carbon flow toward nucleic acid and fatty acid synthesis in myeloid tumor cells.
2001 Oct 12
Requirement for Mdm2 in the survival effects of Bcr-Abl and interleukin 3 in hematopoietic cells.
2001 Oct 15
[Chronic myeloid leukemia and tyrosine kinase inhibitors].
2001 Sep
Improving the management of chronic myeloid leukaemia.
2001 Sep
[Chronic myelogenous leukemia].
2001 Sep
Pharmacologic inhibition of the Bcr-Abl kinase with STI571: a novel, safe, and effective therapy for chronic myeloid leukemia.
2001 Sep
A possible role for STI571 in the treatment of idiopathic myelofibrosis.
2001 Sep
Treatment of leukemia relapse after allogeneic hematopoietic stem cell transplantation by donor lymphocyte infusion and STI-571.
2001 Sep
Inhibition of tyrosine kinase activity induces caspase-dependent apoptosis in anaplastic large cell lymphoma with NPM-ALK (p80) fusion protein.
2001 Sep
Cancer in the crosshairs.
2001 Sep
Adhesion to fibronectin selectively protects Bcr-Abl+ cells from DNA damage-induced apoptosis.
2001 Sep 1
Cancer treatment in the STI571 era: what will change?
2001 Sep 15
Roots of clinical resistance to STI-571 cancer therapy.
2001 Sep 21
Roots of clinical resistance to STI-571 cancer therapy.
2001 Sep 21
Involvement of Jak2 tyrosine phosphorylation in Bcr-Abl transformation.
2001 Sep 27
Small molecule: large hopes.
2001 Sep-Oct
Patents

Sample Use Guides

In Vivo Use Guide
The prescribed dose should be administered orally, with a meal and a large glass of water. Doses of 400 mg or 600 mg should be administered once daily, whereas a dose of 800 mg should be administered as 400 mg twice a day. Treatment may be continued as long as there is no evidence of progressive disease or unacceptable toxicity.
Route of Administration: Oral
In Vitro Use Guide
Imatinib (CGP 57148) was tested for growth inhibition of EGF-dependent BALB/MK cells, the H-ras-transformed T24 bladder carcinoma line, and IL-3-dependent growth of FDC-Pl cells. The compound showed only weak antiproliferative activity against these cell lines, with IC50 values of 12.7 uM, 9.4 uM, and 29.2 uM, respectively. However, when tested on v-abl-transformed PB-3c cells, incubation with CGP 57148 resulted in potent growth inhibition even in the presence of exogenous IL-3 (IC50 values, 0.11 uM without IL-3 and 0.9 uM with IL-3). Similar results were obtained using v-sis-transformed BALB/c 3T3 cells, which grow in response to autocrine PDGF production (IC50, 0.33 uM).
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:54:26 UTC 2019
Edited
by admin
on Mon Oct 21 20:54:26 UTC 2019
Record UNII
BKJ8M8G5HI
Record Status Validated (UNII)
Record Version
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Name Type Language
IMATINIB
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
IMATINIB [WHO-DD]
Common Name English
GLAMOX
Brand Name English
IMATINIB [VANDF]
Common Name English
IMATINIB [MI]
Common Name English
IMATINIB [INN]
Common Name English
BENZAMIDE, 4-((4-METHYL-1-PIPERAZINYL)METHYL)-N-(4-METHYL-3-((4-(3-PYRIDINYL)-2-PYRIMIDINYL)AMINOPHENYL)-
Common Name English
IMATINIB [EMA EPAR]
Common Name English
Classification Tree Code System Code
WHO-ATC L01XE01
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
EMA ASSESSMENT REPORTS IMANTINIB TEVA (AUTHORIZED: LEUKEMIA, , MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE)
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
LIVERTOX 500
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
EU-Orphan Drug EU/3/14/1357
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
FDA ORPHAN DRUG 208905
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
NDF-RT N0000175076
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
NCI_THESAURUS C155700
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
FDA ORPHAN DRUG 303810
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
EMA ASSESSMENT REPORTS IMANTINIB ACTAVIS (AUTHORIZED: LEUKEMIA, , MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE)
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
EMA ASSESSMENT REPORTS GLIVEC (AUTHORIZED: GASTROINTESTINAL STROMAL TUMORS)
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB MEDAC (AUTHORIZED DERMATOFIBROSARCOMA)
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
FDA ORPHAN DRUG 140100
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
NDF-RT N0000175605
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
EMA ASSESSMENT REPORTS IMANTIB ACCORD (AUTHORIZED: DERMATOFIBROSARCOMA)
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
WHO-VATC QL01XE01
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
Code System Code Type Description
DRUG BANK
DB00619
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
PUBCHEM
5291
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
MESH
C097613
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
EVMPD
SUB25387
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
EPA CompTox
152459-95-5
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
RXCUI
282388
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
IMATINIB
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
INN
8031
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
LactMed
152459-95-5
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
NCI_THESAURUS
C62035
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
MERCK INDEX
M6213
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY Merck Index
IUPHAR
5687
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
ChEMBL
CHEMBL941
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
CAS
152459-95-5
Created by admin on Mon Oct 21 20:54:26 UTC 2019 , Edited by admin on Mon Oct 21 20:54:26 UTC 2019
PRIMARY
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