brepocitinib   Click here for help

GtoPdb Ligand ID: 10459

Synonyms: compound 23 [PMID: 30113844] | PF-06700841 | PF06700841
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Brepocitinib (PF-06700841) is a dual Janus kinase 1 (JAK1) and TYK2 inhibitor [1]. It is proposed for treating autoimmune and other inflammatory conditions. Brepocitinib is a Type 1 ATP site inhibitor.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 79.18
Molecular weight 389.18
XLogP 2.37
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C(C1CC1(F)F)N1C2CCC1CN(C2)c1ccnc(n1)Nc1cnn(c1)C
Isomeric SMILES O=C([C@@H]1CC1(F)F)N1[C@@H]2CC[C@H]1CN(C2)c1ccnc(n1)Nc1cnn(c1)C
InChI InChI=1S/C18H21F2N7O/c1-25-8-11(7-22-25)23-17-21-5-4-15(24-17)26-9-12-2-3-13(10-26)27(12)16(28)14-6-18(14,19)20/h4-5,7-8,12-14H,2-3,6,9-10H2,1H3,(H,21,23,24)/t12-,13+,14-/m0/s1
InChI Key BUWBRTXGQRBBHG-MJBXVCDLSA-N
References
1. Fensome A, Ambler CM, Arnold E, Banker ME, Brown MF, Chrencik J, Clark JD, Dowty ME, Efremov IV, Flick A et al.. (2018)
Dual Inhibition of TYK2 and JAK1 for the Treatment of Autoimmune Diseases: Discovery of (( S)-2,2-Difluorocyclopropyl)((1 R,5 S)-3-(2-((1-methyl-1 H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841).
J. Med. Chem., 61 (19): 8597-8612. [PMID:30113844]