avapritinib   

GtoPdb Ligand ID: 10368

Synonyms: Ayvakit® | BLU-285 | BLU285
avapritinib is an approved drug (FDA (2020))
Compound class: Synthetic organic
Comment: Avapritinib (BLU-285) was developed by Blueprint Medicines as an oral precision therapy to selectively and potently inhibit KIT and PDGFRA mutant kinases [2]. It is a Type I kinase inhibitor that binds the active kinase conformation. Avapritinib 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 such switch control inhibitor is ripretinib.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 106.29
Molecular weight 498.24
XLogP 4.21
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Fc1ccc(cc1)C(c1cnc(nc1)N1CCN(CC1)c1ncnn2c1cc(c2)c1cnn(c1)C)(N)C
Isomeric SMILES Fc1ccc(cc1)[C@@](c1cnc(nc1)N1CCN(CC1)c1ncnn2c1cc(c2)c1cnn(c1)C)(N)C
InChI InChI=1S/C26H27FN10/c1-26(28,20-3-5-22(27)6-4-20)21-13-29-25(30-14-21)36-9-7-35(8-10-36)24-23-11-18(16-37(23)33-17-31-24)19-12-32-34(2)15-19/h3-6,11-17H,7-10,28H2,1-2H3/t26-/m0/s1
InChI Key DWYRIWUZIJHQKQ-SANMLTNESA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
IUPAC Name
(1S)-1-(4-fluorophenyl)-1-[2-[4-[6-(1-methylpyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]piperazin-1-yl]pyrimidin-5-yl]ethanamine
International Nonproprietary Names
INN number INN
10613 avapritinib
Synonyms
Ayvakit® | BLU-285 | BLU285
Comments
Avapritinib (BLU-285) was developed by Blueprint Medicines as an oral precision therapy to selectively and potently inhibit KIT and PDGFRA mutant kinases [2]. It is a Type I kinase inhibitor that binds the active kinase conformation. Avapritinib 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 such switch control inhibitor is ripretinib.
Database Links
CAS Registry No. 1703793-34-3 (source: WHO INN record)
DrugCentral Ligand 5379
GtoPdb PubChem SID 384403648
PubChem CID 118023034
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