dual sEH/FAAH inhibitor 11   Click here for help

GtoPdb Ligand ID: 10124

Synonyms: compound B-11 [WO2017160861] | example 28 [WO2017160861]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Inhibitor 11 was designed as a dual inhibitor of fatty acid amide hydrolase (FAAH) and soluble epoxide hydrolase (sEH), two enzymes that independently down-modulate inflammatory and neuropathic pain [2]. The structure-activity relationship exploration was initiated using the potent FAAH inhibitor PF750 (which is a weak sEH inhibitor). Inhibitor 11 is one of the chemical structures claimed in patent WO2017160861A1, specifically example 28 (B-11) [1]. Inhibitor 11 exhibits favourable target selectivity, pharmacokinetic properties and in vivo target engagement [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 63.69
Molecular weight 539.16
XLogP 6.92
No. Lipinski's rules broken 1
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Canonical SMILES O=C(N1CCC(CC1)Cc1cccc(c1)Oc1ccc(cn1)C(F)(F)F)Nc1ccc(cc1)OC(F)(F)F
Isomeric SMILES O=C(N1CCC(CC1)Cc1cccc(c1)Oc1ccc(cn1)C(F)(F)F)Nc1ccc(cc1)OC(F)(F)F
InChI InChI=1S/C26H23F6N3O3/c27-25(28,29)19-4-9-23(33-16-19)37-22-3-1-2-18(15-22)14-17-10-12-35(13-11-17)24(36)34-20-5-7-21(8-6-20)38-26(30,31)32/h1-9,15-17H,10-14H2,(H,34,36)
Immunopharmacology Comments
Fatty acid amide hydrolase (FAAH) and soluble epoxide hydrolase (sEH) inhibitors are being explored for their capacity to reduce inflammatory and neuropathic pain. Combining the two activities in one molecular structure is hypothesised to improve clinical efficacy when compared to FAAH-inhibition alone, since although several FAAH inhibitors have reported preclinical efficacy, significant pain reduction has not been demonstrated in clinical evaluations.