ponatinib   Click here for help

GtoPdb Ligand ID: 5890

Synonyms: AP24534 | Iclusig®
Approved drug PDB Ligand Immunopharmacology Ligand
ponatinib is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: Ponatinib is a Type-1 kinase inhibitor. It is a third generation BCR-Abl inhibitor. Use of ponatinib is subject to additional monitoring due to the observed serious risk of liver problems or blood clots (including heart attack and stroke, collectively referred to as arterial occlusive events, or AOEs). Final 5-year results of safety and efficacy in Ph+ leukemia as evaluated in NCT01207440 are reported by Cortes et al. (2018) [1].
Marketed formulations contain ponatinib hydrochloride (PubChem CID 46908927).
Ponatinib has also been reported as a dual inhibitor of RIPK1 and RIPK3 which inhibits experimental models of RIPK1- and RIPK3-dependent cell death (necroptosis) [5]. On the basis of these findings, hybrid ponatinib/necrostatin-1 (a RIPK1 and IDO inhibitor) were designed and tested for potential to target RIPK1- and RIPK3-driven inflammatory pathologies.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 65.77
Molecular weight 532.22
XLogP 5.2
No. Lipinski's rules broken 1
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Canonical SMILES CN1CCN(CC1)Cc1ccc(cc1C(F)(F)F)NC(=O)c1ccc(c(c1)C#Cc1cnc2n1nccc2)C
Isomeric SMILES CN1CCN(CC1)Cc1ccc(cc1C(F)(F)F)NC(=O)c1ccc(c(c1)C#Cc1cnc2n1nccc2)C
InChI InChI=1S/C29H27F3N6O/c1-20-5-6-22(16-21(20)8-10-25-18-33-27-4-3-11-34-38(25)27)28(39)35-24-9-7-23(26(17-24)29(30,31)32)19-37-14-12-36(2)13-15-37/h3-7,9,11,16-18H,12-15,19H2,1-2H3,(H,35,39)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2013))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9362 ponatinib
Synonyms Click here for help
AP24534 | Iclusig®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9669717, R-ALL-9679854
Reactome Reaction Reactome logo R-HSA-9669854, R-HSA-9669900, R-HSA-9674430, R-HSA-9674095, R-HSA-9702613, R-HSA-9679839, R-HSA-9693978, R-HSA-9702510, R-HSA-9695831
Other databases
CAS Registry No. 943319-70-8 (source: SciFinder)
ChEBI CHEBI:749637
ChEMBL Ligand CHEMBL1171837
DrugCentral Ligand 4716
GtoPdb PubChem SID 178102513
PubChem CID 24826799
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UniChem Compound Search for chemical match using the InChIKey PHXJVRSECIGDHY-UHFFFAOYSA-N
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Wikipedia Ponatinib

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AP 24534 (links to external site)
Cat. No. 4274