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
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)
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 |
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
Title | Date | PubMed |
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Acute generalized exanthematous pustulosis associated with STI571 in a patient with chronic myeloid leukemia. | 2001 |
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Sarcoma. | 2001 |
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STI571: targeting BCR-ABL as therapy for CML. | 2001 |
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The oncologic four-minute mile. | 2001 |
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Recent advances in the molecular and cellular biology of chronic myeloid leukaemia: lessons to be learned from the laboratory. | 2001 Apr |
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ST1571, a tyrosine kinase inhibitor for the treatment of chronic myelogenous leukemia: validating the promise of molecularly targeted therapy. | 2001 Aug |
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STI571 inactivation of the gastrointestinal stromal tumor c-KIT oncoprotein: biological and clinical implications. | 2001 Aug 16 |
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Cutaneous reactions to STI571. | 2001 Aug 23 |
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Clinical resistance to STI-571 cancer therapy caused by BCR-ABL gene mutation or amplification. | 2001 Aug 3 |
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Bcr-Abl inhibition as a modality of CML therapeutics. | 2001 Aug 31 |
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Mechanisms of resistance imatinib (STI571) in preclinical models and in leukemia patients. | 2001 Feb |
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Perspectives on the future of chronic myeloid leukemia treatment. | 2001 Jul |
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Implications of imatinib mesylate for hematopoietic stem cell transplantation. | 2001 Jul |
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Signal transduction inhibition: results from phase I clinical trials in chronic myeloid leukemia. | 2001 Jul |
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The role of Bcr-Abl in chronic myeloid leukemia and stem cell biology. | 2001 Jul |
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Cancer treatment. New drugs, new hope. | 2001 Jul |
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Clinical trials referral resource. ST1571. | 2001 Jul |
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[Anti-tyrosine kinase: the beginning of molecular therapies of cancer and initial results]. | 2001 Jul |
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Chronic myelogenous leukaemia--new therapeutic principles. | 2001 Jul |
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New leukemia drug receives FDA approval. | 2001 Jul |
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Approval heralds new generation of kinase inhibitors? | 2001 Jul |
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After 30 years of laboratory work, a quick approval for STI571. | 2001 Jul 4 |
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STI571 revolution: can the newer targeted drugs measure up? | 2001 Jul 4 |
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From the Food and Drug Administration. | 2001 Jul 4 |
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ABL-specific tyrosine kinase inhibitor, STI571 in vitro, affects Ph-positive acute lymphoblastic leukemia and chronic myelogenous leukemia in blastic crisis. | 2001 Jun |
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Tyrosine kinase inhibitors in the treatment of chronic myeloid leukaemia: so far so good? | 2001 Jun |
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Quick success for cancer kinase treatment. | 2001 Jun |
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Gleevec (STI-571) for chronic myeloid leukemia. | 2001 Jun 11 |
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Researchers optimistic about sea change in cancer treatment. | 2001 Jun 13 |
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Cancer research. Why some leukemia cells resist STI-571. | 2001 Jun 22 |
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Recent success with the tyrosine kinase inhibitor STI-571--lessons for targeted therapy of cancer. | 2001 Mar |
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Novel therapies for chronic myelogenous leukemia. | 2001 May |
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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 |
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New hope for cancer. | 2001 May 28 |
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Progenitor cells from patients with advanced phase chronic myeloid leukaemia respond to STI571 in vitro and in vivo. | 2001 Nov |
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STI571: a magic bullet? | 2001 Oct |
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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 |
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Improving the management of chronic myeloid leukaemia. | 2001 Sep |
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[Chronic myelogenous leukemia]. | 2001 Sep |
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A possible role for STI571 in the treatment of idiopathic myelofibrosis. | 2001 Sep |
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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 |
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Cancer in the crosshairs. | 2001 Sep |
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Adhesion to fibronectin selectively protects Bcr-Abl+ cells from DNA damage-induced apoptosis. | 2001 Sep 1 |
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Cancer treatment in the STI571 era: what will change? | 2001 Sep 15 |
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Roots of clinical resistance to STI-571 cancer therapy. | 2001 Sep 21 |
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Roots of clinical resistance to STI-571 cancer therapy. | 2001 Sep 21 |
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Involvement of Jak2 tyrosine phosphorylation in Bcr-Abl transformation. | 2001 Sep 27 |
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Small molecule: large hopes. | 2001 Sep-Oct |
Sample Use Guides
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
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
Edited
Mon Oct 21 20:46:32 UTC 2019
by
admin
on
Mon Oct 21 20:46:32 UTC 2019
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Record UNII |
8A1O1M485B
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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
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|
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
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|
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
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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
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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
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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
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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
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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
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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
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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
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|
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
|
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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
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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
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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
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||
|
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
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Code System | Code | Type | Description | ||
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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
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PRIMARY | |||
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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
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PRIMARY | RxNorm | ||
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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
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PRIMARY | |||
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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
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PRIMARY | Merck Index | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY |
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ACTIVE MOIETY |