olorinab   Click here for help

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 was 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 by disrupting recycling of internalized agonist-activated receptors back to the plasma membrane) .
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2D Structure
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Physico-chemical Properties
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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
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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
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Summary of Clinical Use Click here for help
Olorinab (APD371) was evaluated in clinical study for efficacy in the management of visceral pain, specifically the abdominal pain associated with Crohn's disease and IBD. A press release from Arena Pharmaceuticals in March 2021 stated that olorinab had missed its primary endpoint of reducing abdominal pain scores in Phase 2b IBD study NCT04043455.
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