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QuickView for Imatinib (compound)

Name: imatinib
PubChem Compound ID: 10435761
Molecular formula: C29H31N7O
Molecular weight: 492.604 g/mol
Name: imatinib
Name (isomeric): DB00619
Drug Type: small molecule
Imatinib Methansulfonate; STI-571; Imatinib Mesylate
Brand: Gleevec, Glivec
Category: Antineoplastic Agents, Protein Kinase Inhibitors
CAS number: 152459-95-5
Indication: For the treatment Philadelphia chromosome positive chronic myeloid leukemia (CML) and malignant gastrointestinal stromal tumors (GIST).
Imatinib is an antineoplastic agent used to treat chronic myelogenous leukemia. Imatinib is a 2-phenylaminopyrimidine derivative that functions as a specific inhibitor of a number of tyrosine kinase enzymes. In chronic myelogenous leukemia, the Philadelphia chromosome leads to a fusion protein of Abl with Bcr (breakpoint cluster region), termed Bcr...
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Mechanism of Action:
Imatinib mesylate is a protein-tyrosine kinase inhibitor that inhibits the Bcr-Abl tyrosine kinase, the constitutive abnormal tyrosine kinase created by the Philadelphia chromosome abnormality in chronic myeloid leukemia (CML). It inhibits proliferation and induces apoptosis in Bcr-Abl positive cell lines as well as fresh leukemic cells from Philad...
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Absorption: Imatinib is well absorbed with mean absolute bioavailability is 98% with maximum levels achieved within 2-4 hours of dosing
Protein binding: Very high (95%)
Biotransformation: Primarily hepatic via CYP3A4. Other cytochrome P450 enzymes, such as CYP1A2, CYP2D6, CYP2C9, and CYP2C19, play a minor role in its metabolism. The main circulating active metabolite in humans is the N-demethylated piperazine derivative, formed predominantly by CYP3A4.
Route of elimination: Imatinib elimination is predominately in the feces, mostly as metabolites.
Half Life: 18 hours for Imatinib, 40 hours for its major active metabolite, the N-desmethyl derivative
Clearance: 8 L/h [50-year-old CML and GIST patient weighing 50 kg] 14 L/h [50-year-old CML and GIST patient weighing 100 kg]
Toxicity: Side effects include nausea, vomiting, diarrhea, loss of appetite, dry skin, hair loss, swelling (especially in the legs or around the eyes) and muscle cramps
Affected organisms: Humans and other mammals
Food interaction:
Take with food to reduce the incidence of gastric irritation. Follow with a large glass of water. A lipid rich meal will slightly reduce and delay absorption. Avoid grapefruit and grapefruit juice throughout treatment, grapefruit can significantly increase serum levels of this product.
Drug interaction:
AtorvastatinImatinib, a strong CYP3A4 inhibitor, may increase the effect and toxicity of atorvastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of atorvastatin if imatinib is initiated, discontinued or dose changed.
ItraconazoleItraconazole may increase the levels of imatinib.
PimozideImatinib may increase the effect and toxicity of pimozide.
ClarithromycinThe macrolide, clarithromycin, may increase the serum concentration of imatinib.
TamsulosinImatinib, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Imatinib is initiated, discontinued, or dose changed.
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