Structure via PubChem · Public domain (PubChem)
imatinib
Sign in to saveAlso known as STI571, CGP 57148, STI 571, QTI571, alpha-(4-methyl-1-piperazinyl)-3'-{[4-(3-pyridyl)-2-pyrimidinyl]amino}-P-toluidide, 4-(4-methyl-piperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide
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. Imatinib is a small molecule inhibitor targeting multiple tyrosine kinases such as CSF1R, ABL, c-KIT, FLT3, and PDGFR-β. 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 myelo
Key facts
- Drug.verifiedrevid
- 459451238
- Drug.image
- Imatinib2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.image2
- File:Imatinib structure.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 280
- Drug.alt2
- Ball-and-stick model of the imatinib molecule
- Drug.pronounce
- ih-MAT-ih-nib
- Drug.tradename
- Gleevec, Glivec, others
- Drug.MedlinePlus
- a606018
- Drug.DailyMedID
- Imatinib
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth
- Drug.class
- Tyrosine kinase inhibitor
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- EA01
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C29H31N7O
- Molecular weight
- 493.6 g/mol
- IUPAC name
- 4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide
- SMILES
- CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5
- InChIKey
- KTUFNOKKBVMGRW-UHFFFAOYSA-N
- XLogP
- 3.5
- Polar surface area
- 86.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2001
- Admin. routes
- oral
- Indications
- acute lymphoblastic leukemia, acute myeloid leukemia, chronic myelogenous leukemia, clear cell renal carcinoma
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 493.259
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₉H₃₁N₇O
- World Health Organisation international non-proprietary name
- imatinib
- medical condition treated
- dermatofibrosarcoma protuberans
- canonical SMILES
- CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5
- Commons category
- Imatinib
- subject has role
- tyrosine-kinase inhibitor
- physically interacts with
- KIT proto-oncogene, receptor tyrosine kinase
- significant drug interaction
- idelalisib
Sources (7)
via Wikidata · CC0
~28 min read
Encyclopedic overview
28 sectionsContents
- Medical uses
- Chronic myelogenous leukemia
- Gastrointestinal stromal tumors
- Dermatofibrosarcoma protuberans (DFSP)
- Other
- Contraindications and cautions
- Side effects
- Cardiotoxicity
- Childhood growth inhibition
- Pigmentation changes
- Hepatotoxicity
- Overdose
- Interactions
- Pharmacology
- Mechanism of action
- Other pathways affected
- Pharmacokinetics
- Chemistry
- Synthesis
- History
- Society and culture
- Economics
- Controversies
- Patent litigation in India
- Research
- Etymology
- References
- External links
{{infobox drug | verifiedrevid = 459451238 | image = Imatinib2DACS.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = File:Imatinib structure.png | image_class2 = bg-transparent | width2 = 280 | alt2 = Ball-and-stick model of the imatinib molecule | caption = | pronounce = ih-MAT-ih-nib | tradename = Gleevec, Glivec, others | Drugs.com = | MedlinePlus = a606018 | DailyMedID = Imatinib | pregnancy_AU = D | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth | class = Tyrosine kinase inhibitor | ATC_prefix = L01 | ATC_suffix = EA01 | ATC_supplemental = | legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =
| bioavailability = 98% | protein_bound = 95% | metabolism = Liver (mainly CYP3A4-mediated) | metabolites = | onset = | elimination_half-life = 18 h (imatinib)40 h (active metabolite) | duration_of_action = | excretion = Fecal (68%) and kidney (13%)
Excerpted from Wikipedia’s “imatinib” article, available under the CC BY-SA 4.0 licence.