BTK inhibitor 16 [PMID: 30122225]

Ligand id: 10076

Name: BTK inhibitor 16 [PMID: 30122225]

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 97.99
Molecular weight 456.18
XLogP 4.35
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
2-(4-phenoxyphenoxy)-6-[(1S,4S)-2-prop-2-enoyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]pyridine-3-carboxamide
Synonyms
example 90 [US20160264548]
Comments
This compound is reported as an irreversible, covalent inhibitor of Bruton's tyrosine kinase (BTK) [2]. It is compound 23 (example 90) as claimed in Merck's patent US20160264548A1 [1].
Because of its expression pattern on B cells, macrophages, neutrophils, and monocytes (NOT T cells) and its essential role in B lymphocyte development and function, BTK continues to be investigated as a valid therapeutic target for the treatment of diseases that involve B-cell and/or macrophage activation (e.g. B-cell malignancies, asthma and rheumatoid arthritis). Ibrutinib was the first-in-class small molecule BTK inhibitor to reach the clinic. Unfortunately, ibrutinib causes severe adverse effects that are in the main, attributed to its off-target profile. As a result, second-generation BTK inhibitors with optimised structures and improved selectivity are being developed. Inhibitor 16 described here, exhibits comparable cellular potency to ibrutinib but has a higher kinome selectivity against undesirable off-targets.
Database Links
GtoPdb PubChem SID 375973263
PubChem CID 122513214
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