olorinab   

GtoPdb Ligand ID: 10058

Synonyms: APD-371 | APD371 | compound 6 [PMID: 29259753]
Compound class: Synthetic organic
Comment: Olorinab (APD371) is a cannabinoid CB2 receptor agonist that is being developed by Arena Pharmaceuticals as a potential treatment for chronic pain [1]. In vitro, APD371 is as efficacious as the CB2 receptor full agonist CP55940 (as determined by measuring and comparing Emax values), and has limited tachyphylaxis liability (i.e. it does cause agonist-induced desensitization due to impeding the return of internalized agonist-activated receptors back to the plasma membrane) .
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 106.46
Molecular weight 357.18
XLogP 1.19
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCC(C(C)(C)C)NC(=O)c1nn(c2c1CC1C2C1)c1ncc[n+](c1)[O-]
Isomeric SMILES OC[C@H](C(C)(C)C)NC(=O)c1nn(c2c1C[C@H]1[C@@H]2C1)c1ncc[n+](c1)[O-]
InChI InChI=1S/C18H23N5O3/c1-18(2,3)13(9-24)20-17(25)15-12-7-10-6-11(10)16(12)23(21-15)14-8-22(26)5-4-19-14/h4-5,8,10-11,13,24H,6-7,9H2,1-3H3,(H,20,25)/t10-,11-,13+/m0/s1
InChI Key ACSQLTBPYZSGBA-GMXVVIOVSA-N
No information available.
Summary of Clinical Use
APD371 is being evaluated in clinical study for efficacy in the management of visceral pain, specifically the abdominal pain associated with Crohn's disease (see Phase 2 trial NCT03155945).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03155945 Tolerability, Pharmacokinetics, and Efficacy of APD371 in Subjects With Crohn's Disease Experiencing Abdominal Pain Phase 2 Interventional Arena Pharmaceuticals