Imatinib

Imatinib
Clinical data
Trade names	Gleevec, Glivec, others
Other names	STI-571
AHFS/Drugs.com	Monograph
MedlinePlus	a606018
License data	US DailyMed: Imatinib;
Pregnancy; category	AU: D; ;
Routes of; administration	By mouth
Drug class	Tyrosine kinase inhibitor
ATC code	L01EA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	98%
Protein binding	95%
Metabolism	Liver (mainly CYP3A4-mediated)
Elimination 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;
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	STI (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3037125 ;
ECHA InfoCard	100.122.739
Chemical and physical data
Formula	C29H31N7O
Molar mass	493.615 g·mol−1
3D model (JSmol)	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) ; Key:KTUFNOKKBVMGRW-UHFFFAOYSA-N ;
	(verify)

Imatinib, sold under the brand names Gleevec and Glivec (both marketed worldwide by Novartis) among others, is an oral targeted therapy medication used to treat cancer.^[2] Imatinib is a small molecule inhibitor targeting multiple tyrosine kinases such as CSF1R, ABL, c-KIT, FLT3, and PDGFR-β.^[6]^[7] Specifically, it is used for chronic myelogenous leukemia (CML) and acute lymphocytic leukemia (ALL) that are Philadelphia chromosome–positive (Ph⁺), certain types of gastrointestinal stromal tumors (GIST), hypereosinophilic syndrome (HES), chronic eosinophilic leukemia (CEL), systemic mastocytosis, and myelodysplastic syndrome.^[2]

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 can slow growth or result in programmed cell death of certain types of cancer cells.^[2]

Imatinib was approved for medical use in the United States in 2001.^[2] It is on the World Health Organization's List of Essential Medicines.^[8] A generic version became available in the UK as of 2017.^[9]

^ "Imatinib (Gleevec) Use During Pregnancy". Drugs.com. 27 August 2018. Archived from the original on 17 February 2020. Retrieved 16 February 2020.
^ ^a ^b ^c ^d ^e "Imatinib Mesylate". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
^ "Gleevec- imatinib mesylate tablet". DailyMed. 1 March 2024. Retrieved 2 July 2024.
^ "Glivec EPAR". European Medicines Agency. 7 November 2001. Retrieved 2 July 2024.
^ Green KN, Crapser JD, Hohsfield LA (September 2020). "To Kill a Microglia: A Case for CSF1R Inhibitors". Trends in Immunology. 41 (9): 771–784. doi:10.1016/j.it.2020.07.001. PMC 7484341. PMID 32792173.
^ Mun SH, Park PS, Park-Min KH (August 2020). "The M-CSF receptor in osteoclasts and beyond". Experimental & Molecular Medicine. 52 (8): 1239–1254. doi:10.1038/s12276-020-0484-z. PMC 8080670. PMID 32801364.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "Oxford Pharmacy Store Generic Imatinib". oxfordpharmacystore.co.uk. Archived from the original on 2 April 2017. Retrieved 1 April 2017.