tolebrutinib   Click here for help

GtoPdb Ligand ID: 10625

Synonyms: BTK'168 | example 3 [WO2016196840A1] | PRN-2246 | PRN2246 | SAR442168
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Tolebrutinib (PRN2246; SAR442168) is an oral and selective small molecule inhibitor of the enzyme Bruton tyrosine kinase (BTK) [1]. It binds covalently and is brain-penetrant.
The chemical structure that was submitted to the WHO for the INN tolebrutinib is identical to that of example 3 in Principia Biopharma's patent WO2016196840A1 [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 94.86
Molecular weight 455.2
XLogP 2.93
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES C=CC(=O)N1CCCC(C1)n1c(=O)n(c2c1ccnc2N)c1ccc(cc1)Oc1ccccc1
Isomeric SMILES C=CC(=O)N1CCC[C@H](C1)n1c(=O)n(c2c1ccnc2N)c1ccc(cc1)Oc1ccccc1
InChI InChI=1S/C26H25N5O3/c1-2-23(32)29-16-6-7-19(17-29)30-22-14-15-28-25(27)24(22)31(26(30)33)18-10-12-21(13-11-18)34-20-8-4-3-5-9-20/h2-5,8-15,19H,1,6-7,16-17H2,(H2,27,28)/t19-/m1/s1
InChI Key KOEUOFPEZFUWRF-LJQANCHMSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-amino-3-(4-phenoxyphenyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[4,5-c]pyridin-2-one
International Nonproprietary Names Click here for help
INN number INN
11268 tolebrutinib
Synonyms Click here for help
BTK'168 | example 3 [WO2016196840A1] | PRN-2246 | PRN2246 | SAR442168
Database Links Click here for help
CAS Registry No. 1971920-73-6 (source: WHO INN record)
GtoPdb PubChem SID 404859072
PubChem CID 124111565
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