(R)-ARN2508   Click here for help

GtoPdb Ligand ID: 9000

Synonyms: compound (-)-10r [PMID: 26774927] | example 19 [WO2014023643]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: (R)-ARN2508 is an experimental inhibitor of fatty acid amide hydrolase (FAAH) [2], claimed in patent WO2014023643 [1]. The compound series developed by Migliore et al. (2015) [2] is based on a hybrid scaffold combining structural motifs of the FAAH inhibitor URB597 and the COX inhibitor flurbiprofen. The (S) enantiomer ((S)-ARN2508) inhibits both FAAH and COX enzyme activities, whereas this (R) enantiomer only inhibits 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-/m1/s1
Bioactivity Comments
When tested, the racemic mixture of (R) and (S) ARN2508 (compound 10r in [2]) gave IC50 values of 31nM for FAAH, 12nM for COX1 and 430nM for COX2 [2]. 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
Fatty acid amide hydrolase Primary target of this compound Hs Inhibitor Inhibition 8.0 pIC50 - 2
pIC50 8.0 (IC50 9.9x10-9 M) [2]
COX-1 Hs Inhibitor Inhibition 5.4 pIC50 - 2
pIC50 5.4 (IC50 4x10-6 M) [2]
COX-2 Hs Inhibitor Inhibition 4.6 pIC50 - 2
pIC50 4.6 (IC50 2.28x10-5 M) [2]