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
1. Han S, Thoresen L, Jung JK, Zhu X, Thatte J, Solomon M, Gaidarov I, Unett DJ, Yoon WH, Barden J et al.. (2017)
Discovery of APD371: Identification of a Highly Potent and Selective CB2 Agonist for the Treatment of Chronic Pain.
ACS Med Chem Lett, 8 (12): 1309-1313. [PMID:29259753]