ripretinib   Click here for help

GtoPdb Ligand ID: 9175

Synonyms: DCC-2618 | DCC2618 | Quinlock®
Approved drug
ripretinib is an approved drug (FDA (2020))
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
SMILES / InChI / InChIKey
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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)
InChI Key CEFJVGZHQAGLHS-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
IUPAC Name Click here for help
1-[4-bromo-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-phenylurea
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
CAS Registry No. 1442472-39-0 (source: PubChem)
GtoPdb PubChem SID 315661258
PubChem CID 71584930
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