GtoPdb Ligand ID: 9718

Synonyms: GSK-2256294 | GSK-2256294A | GSK2256294A
Compound class: Synthetic organic
Comment: GSK2256294 is an epoxide hydrolase 2 (sEH) inhibitor.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 115.62
Molecular weight 447.2
XLogP 2.78
No. Lipinski's rules broken 0
Canonical SMILES CNc1nc(NC2CCCC(C2)C(=O)NCc2ccc(cc2C(F)(F)F)C#N)nc(n1)C
Isomeric SMILES CNc1nc(N[C@H]2CCC[C@H](C2)C(=O)NCc2ccc(cc2C(F)(F)F)C#N)nc(n1)C
InChI InChI=1S/C21H24F3N7O/c1-12-28-19(26-2)31-20(29-12)30-16-5-3-4-14(9-16)18(32)27-11-15-7-6-13(10-25)8-17(15)21(22,23)24/h6-8,14,16H,3-5,9,11H2,1-2H3,(H,27,32)(H2,26,28,29,30,31)/t14-,16+/m1/s1
No information available.
Summary of Clinical Use
GSK2256294 has completed Phase 1 clinical trials in healthy volunteers and patients with COPD (NCT01762774). Results indicate that the drug showed sustained inhibition of sEH activity and was well-tolerated [2]. A Phase 1/2 trial in patients with subarachnoid hemorrhage is being planned (NCT03318783, as of Nov 2017).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01762774 A Study to Assess the Safety, Tolerability, Pharmacokinetics and Pharmacodynamics of Single Doses of GSK2256294 in Healthy Volunteers, and Single and Repeat Doses of GSK2256294 in Adult Male Moderately Obese Smokers Phase 1 Interventional GlaxoSmithKline
NCT03318783 Subarachnoid Hemorrhage and Soluble Epoxide Hydrolase Inhibition Trial Phase 1/Phase 2 Interventional Oregon Health and Science University