orelabrutinib   Click here for help

GtoPdb Ligand ID: 10629

Synonyms: example 3 [WO2015048662A2] | ICP-022 | ICP022
Approved drug Immunopharmacology Ligand
orelabrutinib is an approved drug (China (2020))
Compound class: Synthetic organic
Comment: The chemical structure that was submitted to the WHO for the INN orelabrutinib, is identical to the structure of example 3 that is claimed as a BTK inhibitor in patent WO2015048662A2 [2]. The inhibitors in WO2015048662A2 are claimed for their potential to treat cancers [1] and inflammatory/autoimmune diseases that are mediated, at least in part, by Bruton's tyrosine kinase (BTK). Innocare Pharma have declared the ICP-022>orelabrutinib association on their company news webpage. Orelabrutinib is an orally administered, potent, irreversible and selective BTK-inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 85.52
Molecular weight 427.19
XLogP 3.62
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES C=CC(=O)N1CCC(CC1)c1ccc(c(n1)c1ccc(cc1)Oc1ccccc1)C(=O)N
Isomeric SMILES C=CC(=O)N1CCC(CC1)c1ccc(c(n1)c1ccc(cc1)Oc1ccccc1)C(=O)N
InChI InChI=1S/C26H25N3O3/c1-2-24(30)29-16-14-18(15-17-29)23-13-12-22(26(27)31)25(28-23)19-8-10-21(11-9-19)32-20-6-4-3-5-7-20/h2-13,18H,1,14-17H2,(H2,27,31)
InChI Key MZPVEMOYADUARK-UHFFFAOYSA-N
References
1. Bond DA, Maddocks KJ. (2020)
Current Role and Emerging Evidence for Bruton Tyrosine Kinase Inhibitors in the Treatment of Mantle Cell Lymphoma.
Hematol Oncol Clin North Am, 34 (5): 903-921. [PMID:32861286]
2. Chen X, Gao Y, Liu C, Ni H, Mulvihill M. (2015)
Substituted nicotinimide inhibitors of btk and their preparation and use in the treatment of cancer, inflammation and autoimmune disease.
Patent number: WO2015048662A2. Assignee: X-Rx Discovery, Inc.. Priority date: 03/09/2013. Publication date: 02/04/2015.
3. Dhillon S. (2021)
Orelabrutinib: First Approval.
Drugs, [Epub ahead of print]. DOI: 10.1007/s40265-021-01482-5 [PMID:33704654]