ropsacitinib   Click here for help

GtoPdb Ligand ID: 11613

Synonyms: compound 22 [PMID: 32787094] | PF-06826647 | PF06826647 | Tyk2-IN-8
Compound class: Synthetic organic
Comment: Ropsacitinib (PF-06826647) is claimed as a tyrosine kinase 2 (TYK2) Inhibitor [1]. However, its activity at clinically relevant concentrations to achieve TYK2 inhibition is suggestive of significant inhibition of at least JAK2, if not also of JAK1 [3]. Ropsacitinib is an ATP-competitive inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 113.41
Molecular weight 383.16
XLogP 1.08
No. Lipinski's rules broken 0
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Canonical SMILES N#CCC1(CC(C1)C#N)n1ncc(c1)c1nc(cn2c1ccn2)c1cnn(c1)C
Isomeric SMILES N#CCC1(CC(C1)C#N)n1ncc(c1)c1nc(cn2c1ccn2)c1cnn(c1)C
InChI InChI=1S/C20H17N9/c1-27-11-15(9-24-27)17-13-28-18(2-5-23-28)19(26-17)16-10-25-29(12-16)20(3-4-21)6-14(7-20)8-22/h2,5,9-14H,3,6-7H2,1H3
1. Gerstenberger BS, Ambler C, Arnold EP, Banker ME, Brown MF, Clark JD, Dermenci A, Dowty ME, Fensome A, Fish S et al.. (2020)
Discovery of Tyrosine Kinase 2 (TYK2) Inhibitor (PF-06826647) for the Treatment of Autoimmune Diseases.
J Med Chem, 63 (22): 13561-13577. [PMID:32787094]
2. Singh RSP, Pradhan V, Roberts ES, Scaramozza M, Kieras E, Gale JD, Peeva E, Vincent MS, Banerjee A, Fensome A et al.. (2021)
Safety and Pharmacokinetics of the Oral TYK2 Inhibitor PF-06826647: A Phase I, Randomized, Double-Blind, Placebo-Controlled, Dose-Escalation Study.
Clin Transl Sci, 14 (2): 671-682. [PMID:33290616]
3. Tehlirian C, Peeva E, Kieras E, Scaramozza M, Roberts ES, Singh RSP, Pradhan V, Banerjee A, Garcet S, Xi L et al.. (2021)
Safety, tolerability, efficacy, pharmacokinetics, and pharmacodynamics of the oral TYK2 inhibitor PF-06826647 in participants with plaque psoriasis: a phase 1, randomised, double-blind, placebo-controlled, parallel-group study.
Lancet Rheumatology, 3 (3): e204-e21. DOI: 10.1016/S2665-9913(20)30397-0