Imatinib mesylate

Imatinib

Clinical data
Trade names	Gleevec, Glivec, others
AHFS/Drugs.com	Monograph
MedlinePlus	a606018
License data	EU EMA: Glivec US FDA: IMATINIB
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	by mouth
ATC code	L01XE01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
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
IUPAC name 4-[(4-methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide
Synonyms	STI-571
CAS Number	152459-95-5 Y
PubChem CID	5291
IUPHAR/BPS	5687
DrugBank	DB00619 Y
ChemSpider	5101 Y
UNII	BKJ8M8G5HI
KEGG	D08066 Y
ChEBI	CHEBI:45783 Y
ChEMBL	CHEMBL941 Y
PDB ligand	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
SMILES Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C
InChI InChI=1S/C29H31N7O/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/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34) Y Key:KTUFNOKKBVMGRW-UHFFFAOYSA-N Y

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.