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Details

Stereochemistry ACHIRAL
Molecular Formula C29H31N7O.CH4O3S
Molecular Weight 589.708
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMATINIB MESYLATE

SMILES

CS(O)(=O)=O.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=YLMAHDNUQAMNNX-UHFFFAOYSA-N
InChI=1S/C29H31N7O.CH4O3S/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;1-5(2,3)4/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34);1H3,(H,2,3,4)

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

Molecular Formula CH4O3S
Molecular Weight 96.106
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
STI571: targeting BCR-ABL as therapy for CML.
2001
The oncologic four-minute mile.
2001
Effect of a selective Abl tyrosine kinase inhibitor, STI571, on in vitro growth of BCR-ABL-positive acute lymphoblastic leukemia cells.
2001 Apr
Mechanisms of transformation by the BCR/ABL oncogene.
2001 Apr
Recent advances in the molecular and cellular biology of chronic myeloid leukaemia: lessons to be learned from the laboratory.
2001 Apr
Inhibition of platelet-derived growth factor receptors reduces interstitial hypertension and increases transcapillary transport in tumors.
2001 Apr 1
ARG tyrosine kinase activity is inhibited by STI571.
2001 Apr 15
Targeting protein kinases for tumor therapy.
2001 Aug
Cutaneous reactions to STI571.
2001 Aug 23
Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amplification.
2001 Aug 3
Mechanisms of resistance imatinib (STI571) in preclinical models and in leukemia patients.
2001 Feb
Perspectives on the future of chronic myeloid leukemia treatment.
2001 Jul
Interferon-alfa-based treatment of chronic myeloid leukemia and implications of signal transduction inhibition.
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
[Leukemogenesis and new therapy development: the example of chronic myelogenous leukemia].
2001 Jul
New leukemia drug receives FDA approval.
2001 Jul
Approval heralds new generation of kinase inhibitors?
2001 Jul
Anti-cancer drug success emerges from molecular biology origins.
2001 Jul
STI571 revolution: can the newer targeted drugs measure up?
2001 Jul 4
From the Food and Drug Administration.
2001 Jul 4
Current treatment approaches for chronic myelogenous leukemia.
2001 Jul-Aug
Gastrointestinal stromal tumor workshop.
2001 Jun
ABL-specific tyrosine kinase inhibitor, STI571 in vitro, affects Ph-positive acute lymphoblastic leukemia and chronic myelogenous leukemia in blastic crisis.
2001 Jun
Tyrosine kinase inhibitors in the treatment of chronic myeloid leukaemia: so far so good?
2001 Jun
Quick success for cancer kinase treatment.
2001 Jun
Gleevec (STI-571) for chronic myeloid leukemia.
2001 Jun 11
Researchers optimistic about sea change in cancer treatment.
2001 Jun 13
Cancer research. Why some leukemia cells resist STI-571.
2001 Jun 22
Tyrosine kinase inhibitor STI571 enhances thyroid cancer cell motile response to Hepatocyte Growth Factor.
2001 Jun 28
Promising clinical trials on kinase inhibitor.
2001 Mar
Sensitivity to the abl inhibitor STI571 in fresh leukaemic cells obtained from chronic myelogenous leukaemia patients in different stages of disease.
2001 Mar
Co-treatment with As2O3 enhances selective cytotoxic effects of STI-571 against Brc-Abl-positive acute leukemia cells.
2001 May
STI571: a gene product-targeted therapy for leukemia.
2001 May
Growth-inhibitory effect of STI571 on cells transformed by the COL1A1/PDGFB rearrangement.
2001 May 1
In search of the silver bullet.
2001 May 14
Tyrosine kinase inhibitor STI571 potentiates the pharmacologic activity of retinoic acid in acute promyelocytic leukemia cells: effects on the degradation of RARalpha and PML-RARalpha.
2001 May 15
Cancer's mechanics. Targeting errant cells.
2001 May 21
New hope for cancer.
2001 May 28
Requirement for Mdm2 in the survival effects of Bcr-Abl and interleukin 3 in hematopoietic cells.
2001 Oct 15
Improving the management of chronic myeloid leukaemia.
2001 Sep
[Chronic myelogenous leukemia].
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
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
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 20:46:32 UTC 2019
Edited
by admin
on Mon Oct 21 20:46:32 UTC 2019
Record UNII
8A1O1M485B
Record Status Validated (UNII)
Record Version
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Name Type Language
IMATINIB MESYLATE
HSDB   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
IMATINIB MESYLATE [USAN]
Common Name English
IMATINIB METHANE SULFONATE
Common Name English
IMATINIB METHANESULFONATE
MI  
Common Name English
IMATINIB ACCORD
Brand Name English
IMATINIB MESILATE [MART.]
Common Name English
IMATINIB MESILATE
JAN   MART.   WHO-DD  
Common Name English
IMATINIB MESYLATE [ORANGE BOOK]
Common Name English
IMATINIB MESYLATE [HSDB]
Common Name English
GLIVEC
Common Name English
BENZAMIDE, 4-((4-METHYL-1-PIPERAZINYL)METHYL)-N-(4-METHYL-3-((4-(3-PYRIDINYL)-2-PYRIMIDINYL)AMINOPHENYL)-, METHANESULFONATE SALT
Common Name English
BENZAMIDE, 4-((4-METHYL-1-PIPERAZINYL)METHYL)-N-(4-METHYL-3-((4-(3-PYRIDINYL)-2-PYRIMIDINYL)AMINOPHENYL)-, METHANESULPHONATE SALT
Common Name English
IMATINIB MESYLATE [VANDF]
Common Name English
IMATINIB MESILATE [JAN]
Common Name English
IMATINIB MEDAC
Brand Name English
GLEEVEC
Brand Name English
STI571
Code English
IMATINIB METHANESULFONATE [MI]
Common Name English
IMATINIB MESILATE [WHO-DD]
Common Name English
STI-571
Code English
STI 571
Code English
IMATINIB (AS MESILATE)
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 209005
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB ACCORD (AUTHORIZED: PRECURSOR CELL LYMPHOBLASTIC LEUKEMIA-LYMPHOMA
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB MEDAC (AUTHORIZED: HYPEREOSINOPHILIC SYNDROME)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB ACTAVIS (AUTHORIZED: LEUKEMIA, MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS GLIVEC (AUTHORIZED: LEUKEMIA, MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS GLIVEC (AUTHORIZED: PRECURSOR CELL LYMPHOBLASTIC LEUKEMIA-LYMPHOMA)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
FDA ORPHAN DRUG 209205
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
FDA ORPHAN DRUG 149201
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
NCI_THESAURUS C155700
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB MEDAC (AUTHORIZED: MYELODYPLASTIC-MYELOPROLIFERATIVE DISEASES)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS GLIVEC (AUTHORIZED: HYPEREOSINOPHILIC SYNDROME)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS GLIVEC (AUTHORIZED: MYELODYPLASTIC-MYELOPROLIFERATIVE DISEASES)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB ACCORD (AUTHORIZED: MYELODYPLASTIC-MYELOPROLIFERATIVE DISEASES)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB MEDAC (AUTHORIZED: PRECURSOR CELL LYMPHOBLASTIC LEUKEMIA-LYMPHOMA)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
FDA ORPHAN DRUG 428914
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB ACCORD (AUTHORIZED: LEUKEMIA, MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
FDA ORPHAN DRUG 209105
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB ACCORD (AUTHORIZED:HYPEREOSINOPHILIC SYNDROME)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EU-Orphan Drug EU/3/01/021
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB TEVA (AUTHORIZED:
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
FDA ORPHAN DRUG 208805
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
EMA ASSESSMENT REPORTS IMATINIB MEDAC (AUTHORIZED: LEUKEMIA, MYELOMONOCYTIC, CHRONIC)
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
Code System Code Type Description
HSDB
220127-57-1
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY
RXCUI
284924
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY RxNorm
EPA CompTox
220127-57-1
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY
MERCK INDEX
M6213
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY Merck Index
EVMPD
SUB12517MIG
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY
PUBCHEM
123596
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY
ChEMBL
CHEMBL941
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY
NCI_THESAURUS
C1687
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY
CAS
220127-57-1
Created by admin on Mon Oct 21 20:46:32 UTC 2019 , Edited by admin on Mon Oct 21 20:46:32 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY