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Imatinib information


Imatinib
Ball-and-stick model of the imatinib molecule
Clinical data
Trade namesGleevec, Glivec, others
Other namesSTI-571
AHFS/Drugs.comMonograph
MedlinePlusa606018
License data
  • US DailyMed: Imatinib
Pregnancy
category
  • AU: D[1]
Routes of
administration
By mouth
Drug classTyrosine kinase inhibitor[2]
ATC code
  • L01EA01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[3]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability98%
Protein binding95%
MetabolismLiver (mainly CYP3A4-mediated)
Elimination half-life18 h (imatinib)
40 h (active metabolite)
ExcretionFecal (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 checkY
    220127-57-1 (mesilate)
PubChem CID
  • 5291
IUPHAR/BPS
  • 5687
DrugBank
  • DB00619 checkY
ChemSpider
  • 5101 checkY
UNII
  • BKJ8M8G5HI
KEGG
  • D08066 checkY
ChEBI
  • CHEBI:45783 checkY
ChEMBL
  • ChEMBL941 checkY
PDB ligand
  • STI (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID3037125 Edit this at Wikidata
ECHA InfoCard100.122.739 Edit this at Wikidata
Chemical and physical data
FormulaC29H31N7O
Molar mass493.615 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) checkY
  • Key:KTUFNOKKBVMGRW-UHFFFAOYSA-N checkY
  (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.[4][5] 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.[2] Severe side effects may include fluid retention, gastrointestinal bleeding, bone marrow suppression, liver problems, and heart failure.[2] Use during pregnancy may result in harm to the baby.[2] Imatinib works by stopping the Bcr-Abl tyrosine-kinase.[2] 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.[6] A generic version became available in the UK as of 2017.[7]

  1. ^ "Imatinib (Gleevec) Use During Pregnancy". Drugs.com. 27 August 2018. Archived from the original on 17 February 2020. Retrieved 16 February 2020.
  2. ^ a b c d e f g h i "Imatinib Mesylate". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
  3. ^ "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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ "Oxford Pharmacy Store Generic Imatinib". oxfordpharmacystore.co.uk. Archived from the original on 2 April 2017. Retrieved 1 April 2017.

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