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Imatinib

Imatinib
Imatinib2DACS.svg
Ball-and-stick model of the imatinib molecule
Clinical data
Trade names Gleevec, Glivec, others
AHFS/Drugs.com Monograph
MedlinePlus a606018
License data
Pregnancy
category
  • AU: D
  • US: D (Evidence of risk)
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 YesY
220127-57-1 (mesilate)
PubChem (CID) 5291
IUPHAR/BPS 5687
DrugBank DB00619 YesY
ChemSpider 5101 YesY
UNII BKJ8M8G5HI YesY
KEGG D08066 YesY
ChEBI CHEBI:45783 YesY
ChEMBL CHEMBL941 YesY
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
1IEP.png
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.


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Wikipedia

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