ripretinib   Click here for help

GtoPdb Ligand ID: 9175

Synonyms: DCC-2618 | DCC2618 | Quinlock®
Approved drug
ripretinib is an approved drug (FDA (2020), EMA (2021))
Compound class: Synthetic organic
Comment: Ripretinib (DCC-2618) is an orally bioavailable, potent pan-KIT and PDGFRα kinase inhibitor that was developed by Dicephera Pharmaceuticals. It was designed for the treatment of malignancies that are driven by KIT and/or PDGFRα, for example gastrointestinal stromal tumors, glioblastoma multiforme and systemic mastocytosis. Ripretinib has activity across a broad range of resistance mutations in its target kinases, that emerge in response to imatinib treatment. Ripretinib binds to the 'switch pocket' of KIT, a domain that regulates the enzyme's catalytic conformation. Compounds that act in this way are often referred to as switch control inhibitors [1]. Another example of a switch control inhibitor is avapritinib.
The chemical structure shown here matches that supplied to the WHO for the INN, and this is claimed in patent WO2010051373 [2] as Example 39. Note that some PubChem SIDs are linked to an incorrect structure (as represented in PubChem CID 46208890).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 88.05
Molecular weight 509.09
XLogP 5.71
No. Lipinski's rules broken 1
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Canonical SMILES CNc1ncc2c(c1)n(CC)c(=O)c(c2)c1cc(NC(=O)Nc2ccccc2)c(cc1Br)F
Isomeric SMILES CNc1ncc2c(c1)n(CC)c(=O)c(c2)c1cc(NC(=O)Nc2ccccc2)c(cc1Br)F
InChI InChI=1S/C24H21BrFN5O2/c1-3-31-21-12-22(27-2)28-13-14(21)9-17(23(31)32)16-10-20(19(26)11-18(16)25)30-24(33)29-15-7-5-4-6-8-15/h4-13H,3H2,1-2H3,(H,27,28)(H2,29,30,33)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020), EMA (2021))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10808 ripretinib
Synonyms Click here for help
DCC-2618 | DCC2618 | Quinlock®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9674322
Reactome Reaction Reactome logo R-HSA-9674095, R-HSA-9681375, R-HSA-9681382, R-HSA-9674430
Other databases
CAS Registry No. 1442472-39-0 (source: PubChem)
DrugCentral Ligand 5394
GtoPdb PubChem SID 315661258
PubChem CID 71584930
Search Google for chemical match using the InChIKey CEFJVGZHQAGLHS-UHFFFAOYSA-N
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UniChem Compound Search for chemical match using the InChIKey CEFJVGZHQAGLHS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CEFJVGZHQAGLHS-UHFFFAOYSA-N