(S)-ARN2508   Click here for help

GtoPdb Ligand ID: 8999

Synonyms: compound (+)-10r [PMID: 26774927] | example 20 [WO2014023643]
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: (S)-ARN2508 is a dual inhibitor of fatty acid amide hydrolase (FAAH) and COX enzyme activities [3], claimed in patent WO2014023643 [1]. The compound series developed by Migliore et al. (2015) [3] is based on a hybrid scaffold combining structural motifs of the FAAH inhibitor URB597 and the COX inhibitor flurbiprofen. From this series, the (S) enantiomer was found to inhibit both enzymes, whereas the (R) enantiomer ((R)-ARN2508) only inhibited FAAH.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 75.63
Molecular weight 387.18
XLogP 5.68
No. Lipinski's rules broken 1
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Canonical SMILES CCCCCCNC(=O)Oc1cccc(c1)c1ccc(cc1F)C(C(=O)O)C
Isomeric SMILES CCCCCCNC(=O)Oc1cccc(c1)c1ccc(cc1F)[C@@H](C(=O)O)C
InChI InChI=1S/C22H26FNO4/c1-3-4-5-6-12-24-22(27)28-18-9-7-8-17(13-18)19-11-10-16(14-20(19)23)15(2)21(25)26/h7-11,13-15H,3-6,12H2,1-2H3,(H,24,27)(H,25,26)/t15-/m0/s1
Bioactivity Comments
When tested, the racemic mixture of (R) and (S) ARN2508 (compound 10r in [3]) gave IC50 values of 31nM for FAAH, 12nM for COX1 and 430nM for COX2 [3]. Note that the (S) enantiomer is the much more potent COX inhibitor, being ~14000 times more potent for COX1 and 1900 times more potent for COX2 than the (R) enantiomer.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
COX-1 Primary target of this compound Hs Inhibitor Inhibition 9.5 pIC50 - 3
pIC50 9.5 (IC50 2.9x10-10 M) [3]
Fatty acid amide hydrolase Primary target of this compound Hs Inhibitor Inhibition 8.0 pIC50 - 3
pIC50 8.0 (IC50 9.4x10-9 M) [3]
COX-2 Hs Inhibitor Inhibition 7.9 pIC50 - 3
pIC50 7.9 (IC50 1.2x10-8 M) [3]