difamilast   Click here for help

GtoPdb Ligand ID: 9776

Synonyms: example 352 [WO2007058338] | MM36 | OPA-15406
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Difamilast (OPA-15406) is a topical, selective, nonsteroidal PDE4 inhibitor that is being developed for the treatment of atopic dermatitis [1]. The chemical structure is claimed as example 352 in patent WO2007058338 [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 82.82
Molecular weight 446.17
XLogP 4.74
No. Lipinski's rules broken 0
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Canonical SMILES CCOc1ccccc1C(=O)NCc1coc(n1)c1ccc(c(c1)OC(C)C)OC(F)F
Isomeric SMILES CCOc1ccccc1C(=O)NCc1coc(n1)c1ccc(c(c1)OC(C)C)OC(F)F
InChI InChI=1S/C23H24F2N2O5/c1-4-29-18-8-6-5-7-17(18)21(28)26-12-16-13-30-22(27-16)15-9-10-19(32-23(24)25)20(11-15)31-14(2)3/h5-11,13-14,23H,4,12H2,1-3H3,(H,26,28)
Bioactivity Comments
OPA-15406 exhibits high selectivity for the PDE4B isoform [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphodiesterase 4D Hs Inhibitor Inhibition >7.3 pIC50 - 2
pIC50 >7.3 (IC50 <5x10-8 M) [2]
Description: Measuring inhibition of substrate hydrolysis by the PDE4D3 isoform.