Editing Imatinib (section)

{{Short description|Chemical compound}}
{{Use dmy dates|date=March 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{infobox drug
| verifiedrevid      = 459451238
| image              = Imatinib2DACS.svg
| image_class        = skin-invert-image
| width              = 250
| alt                = 
| image2             = File:Imatinib structure.png
| width2             = 280
| alt2               = Ball-and-stick model of the imatinib molecule
| caption            = 

<!-- Clinical data -->
| pronounce          = 
| tradename          = Gleevec, Glivec, others
| Drugs.com          = {{drugs.com|monograph|imatinib-mesylate}}
| MedlinePlus        = a606018
| DailyMedID         = Imatinib
| pregnancy_AU       = D
| pregnancy_AU_comment =<ref name="Drugs.com pregnancy">{{cite web | title=Imatinib (Gleevec) Use During Pregnancy | publisher=Drugs.com | date=27 August 2018 |url=https://www.drugs.com/pregnancy/imatinib.html | access-date=16 February 2020 | archive-date=17 February 2020 | archive-url=https://web.archive.org/web/20200217055034/https://www.drugs.com/pregnancy/imatinib.html | url-status=live }}</ref>
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]]
| class              = [[Tyrosine kinase inhibitor]]<ref name=AHFS2017>{{cite web|title=Imatinib Mesylate|url=https://www.drugs.com/monograph/imatinib-mesylate.html|publisher=The American Society of Health-System Pharmacists|access-date=8 January 2017|url-status=live|archive-url=https://web.archive.org/web/20170116192526/https://www.drugs.com/monograph/imatinib-mesylate.html|archive-date=16 January 2017}}</ref>
| ATC_prefix         = L01
| ATC_suffix         = EA01
| ATC_supplemental   = 

<!-- Legal status -->
| legal_AU           = S4
| legal_AU_comment =<ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 |url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024 | archive-date=6 July 2023 | archive-url=https://web.archive.org/web/20230706023149/https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | url-status=live }}</ref>
| legal_BR           = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment   = 
| legal_CA           = Rx-only
| legal_CA_comment   = 
| legal_DE           = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment   = 
| legal_NZ           = <!-- Class A, B, C -->
| legal_NZ_comment   = 
| legal_UK           = POM
| legal_UK_comment   = 
| legal_US           = Rx-only
| legal_US_comment   = <ref name="Gleevec FDA label">{{cite web | title=Gleevec- imatinib mesylate tablet | website=DailyMed | date=1 March 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=211ef2da-2868-4a77-8055-1cb2cd78e24b | access-date=2 July 2024}}</ref><ref name="Imkeldi FDA label">{{cite web | title=Imkeldi- imatinib oral solution | website=DailyMed | date=5 December 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=26658bb7-9ba1-a10e-e063-6394a90a172e | access-date=23 December 2024}}</ref>
| legal_EU           = Rx-only
| legal_EU_comment   = <ref name="Glivec EPAR">{{cite web | title=Glivec EPAR | website=European Medicines Agency | date=7 November 2001 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/glivec | access-date=2 July 2024}}</ref>
| legal_UN           = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment   = 
| legal_status       = <!--For countries not listed above-->

<!-- Pharmacokinetic data -->
| bioavailability    = 98%
| protein_bound      = 95%
| metabolism         = [[Liver]] (mainly [[CYP3A4]]-mediated)
| metabolites        = 
| onset              = 
| elimination_half-life = 18 h (imatinib)<br />40 h (active metabolite)
| duration_of_action = 
| excretion          = Fecal (68%) and [[kidney]] (13%)

<!-- Identifiers -->
| CAS_number_Ref     = {{cascite|correct|??}}
| CAS_number         = 152459-95-5
| CAS_supplemental   = <br />{{CAS|220127-57-1}}(mesilate)
| PubChem            = 5291
| IUPHAR_ligand      = 5687
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = DB00619
| ChemSpiderID_Ref   = {{chemspidercite|correct|chemspider}}
| ChemSpiderID       = 5101
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = BKJ8M8G5HI
| KEGG_Ref           = {{keggcite|correct|kegg}}
| KEGG               = D08066
| ChEBI_Ref          = {{ebicite|correct|EBI}}
| ChEBI              = 45783
| ChEMBL_Ref         = {{ebicite|correct|EBI}}
| ChEMBL             = 941
| NIAID_ChemDB       = 
| PDB_ligand         = STI
| synonyms           = STI-571

<!-- Chemical and physical data -->
| IUPAC_name         = 4-[(4-methylpiperazin-1-yl)methyl]-''N''-(4-methyl-3-<nowiki/>{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide
| C                  = 29
| H                  = 31
| N                  = 7
| O                  = 1
| SMILES             = Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 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)
| StdInChI_comment   = 
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = KTUFNOKKBVMGRW-UHFFFAOYSA-N
| density            = 
| density_notes      = 
| melting_point      = 
| melting_high       = 
| melting_notes      = 
| boiling_point      = 
| boiling_notes      = 
| solubility         = 
| sol_units          = 
| specific_rotation  = 
}}

<!-- Definition and medical uses -->
'''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]].<ref name=AHFS2017/> Imatinib is a small molecule inhibitor targeting multiple [[tyrosine kinase]]s such as [[Colony stimulating factor 1 receptor|CSF1R]], [[ABL (gene)|ABL]], [[KIT (gene)|c-KIT]], [[FLT3]], and [[PDGFR-β]].<ref>{{cite journal | vauthors = Green KN, Crapser JD, Hohsfield LA | title = To Kill a Microglia: A Case for CSF1R Inhibitors | journal = Trends in Immunology | volume = 41 | issue = 9 | pages = 771–784 | date = September 2020 | pmid = 32792173 | pmc = 7484341 | doi = 10.1016/j.it.2020.07.001 }}</ref><ref>{{cite journal | vauthors = Mun SH, Park PS, Park-Min KH | title = The M-CSF receptor in osteoclasts and beyond | journal = Experimental & Molecular Medicine | volume = 52 | issue = 8 | pages = 1239–1254 | date = August 2020 | pmid = 32801364 | pmc = 8080670 | doi = 10.1038/s12276-020-0484-z }}</ref> Specifically, it is used for [[chronic myelogenous leukemia]] (CML) and [[acute lymphocytic leukemia]] (ALL) that are [[Philadelphia chromosome]]–positive (Ph<sup>+</sup>), certain types of [[gastrointestinal stromal tumor]]s (GIST), [[hypereosinophilic syndrome]] (HES), [[chronic eosinophilic leukemia]] (CEL), [[systemic mastocytosis]], and [[myelodysplastic syndrome]].<ref name=AHFS2017/>

<!-- Side effects and mechanism -->
Common side effects include vomiting, diarrhea, muscle pain, headache, and rash. Severe side effects may include [[Water retention (medicine)|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 [[Bcr-Abl tyrosine-kinase inhibitor|stopping the Bcr-Abl tyrosine-kinase]]. This can slow growth or result in [[apoptosis|programmed cell death]] of certain types of cancer cells.<ref name=AHFS2017/>

<!-- History and culture -->
Imatinib was approved for medical use in the United States in 2001.<ref name=AHFS2017/> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> A generic version became available in the UK as of 2017.<ref>{{cite web|title=Oxford Pharmacy Store Generic Imatinib|url=http://oxfordpharmacystore.co.uk/latest_news/generic-imatinib/|website=oxfordpharmacystore.co.uk|access-date=1 April 2017|url-status=live|archive-url=https://web.archive.org/web/20170402081046/http://oxfordpharmacystore.co.uk/latest_news/generic-imatinib/|archive-date=2 April 2017}}</ref>