Clinical data | |
---|---|
Trade names | Gleevec, Glivec, others |
AHFS/Drugs.com | Monograph |
MedlinePlus | a606018 |
License data | |
Pregnancy category |
|
Routes of administration |
by mouth |
ATC code | L01XE01 (WHO) |
Legal status | |
Legal status | |
Pharmacokinetic data | |
Bioavailability | 98% |
Protein binding | 95% |
Metabolism | liver (mainly CYP3A4-mediated) |
Biological half-life | 18 h (imatinib) 40 h (active metabolite) |
Excretion | Fecal (68%) and kidney (13%) |
Identifiers | |
|
|
Synonyms | STI-571 |
CAS Number |
152459-95-5 220127-57-1 (mesilate) |
PubChem (CID) | 5291 |
IUPHAR/BPS | 5687 |
DrugBank | DB00619 |
ChemSpider | 5101 |
UNII | BKJ8M8G5HI |
KEGG | D08066 |
ChEBI | CHEBI:45783 |
ChEMBL | CHEMBL941 |
PDB ligand ID | STI (PDBe, RCSB PDB) |
ECHA InfoCard | 100.122.739 |
Chemical and physical data | |
Formula | C29H31N7O |
Molar mass | 493.603 g/mol 589.7 g/mol (mesilate) |
3D model (Jmol) | Interactive image |
|
|
|
|
Drug mechanism | |
Crystallographic structure of tyrosine-protein kinase ABL (rainbow colored, N-terminus = blue, C-terminus = red) complexed with imatinib (spheres, carbon = white, oxygen = red, nitrogen = blue).
|
|
Therapeutic use | chronic myelogenous leukemia |
---|---|
Biological target | ABL, c-kit, PDGF-R |
Mechanism of action | Tyrosine-kinase inhibitor |
External links | |
ATC code | L01XE01 |
PDB ligand id | STI: PDBe, RCSB PDB |
LIGPLOT | 1iep |
Imatinib, sold under the brand names Gleevec among others, is a chemotherapy medication used to treat cancer. Specifically it is used for chronic myelogenous leukemia (CML) and acute lymphocytic leukemia (ALL) that is Philadelphia chromosome-positive (Ph+) and certain types of gastrointestinal stromal tumors (GIST), , and myelodysplastic syndrome. It is taken by mouth.
Common side effects include vomiting, diarrhea, muscle pain, headache, and rash. Severe side effects may include fluid retention, gastrointestinal bleeding, bone marrow suppression, liver problems, and heart failure. Use during pregnancy may result in harm to the baby. Imatinib works by stopping the Bcr-Abl tyrosine-kinase. This either slows growth or results in programmed cell death of certain type of cancer cells.
Imatinib was approved for medical use in the United States in 2001. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 1,386.49 to 19,162.50 USD a year. In the United States a typical dose for a year has a wholesale cost of $84,408.78, while in the United Kingdom the NHS pays about 20,980.08 pounds.