PRN694

Ligand id: 9285

Name: PRN694

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 107.5
Molecular weight 543.25
XLogP 5.42
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
5-(difluoromethyl)-N-[5-[[[(2S)-3,3-dimethylbutan-2-yl]amino]methyl]-1-[[(2R)-1-prop-2-enoylpyrrolidin-2-yl]methyl]benzimidazol-2-yl]thiophene-2-carboxamide
Database Links
CAS Registry No. 1575818-46-0 (source: PubChem)
PubChem CID 90044055
Search Google for chemical match using the InChIKey NXTKFBGDLDPFLB-PKOBYXMFSA-N
Search Google for chemicals with the same backbone NXTKFBGDLDPFLB
Search UniChem for chemical match using the InChIKey NXTKFBGDLDPFLB-PKOBYXMFSA-N
Search UniChem for chemicals with the same backbone NXTKFBGDLDPFLB
Comments
PRN694 is a small molecule, covalent inhibitor somewhat selective for the TEC family kinases, IL-2-inducible T cell kinase (ITK) and TXK tyrosine kinase (also known as resting lymphocyte kinase or RLK) [2-3]. In vitro PRN694 is a potent inhibitor of Th1 and Th17 differentiation and cytokine production (IFN-γ production for Th1 and IL-17A for Th17), and in vivo PRN694 markedly reduces disease progression in a mouse colitis model [2]. It is suggested that dual ITK and RLK inhibition may represent a novel therapeutic model for amelioration of Th1-mediated inflammatory diseases.
Mechanistically PRN694 inhibits kinase activity by binding irreversibly to cysteine residue 442 of ITK and 350 of RLK [3]. A series of compounds including PRN694 is claimed in patent WO2014036016 [1]. Example 29 is an enantiomer of PRN694 with one unspecified stereocenter.