(S)-ARN2508   

GtoPdb Ligand ID: 8999

Synonyms: compound (+)-10r [PMID: 26774927] | example 20 [WO2014023643]
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.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key USQOVYLRWBOSQC-HNNXBMFYSA-N
No information available.
Mechanism Of Action and Pharmacodynamic Effects
FAAH catalyzes the hydrolysis of anandamide, generating arachidonic acid (AA), which is the substrate of COX. Multi-targeted agents that simultaneously act to inhibit FAAH and COX are being investigated as novel anti-inflammatory therapeutics for the treatment of pain [4]. Concomitant inhibition of FAAH and COX enhances the analgesic effect of NSAIDs ('coxibs') [2], and in addition FAAH inhibition reduces the adverse gastrointestinal side effects caused by COX inhibition [5].