olorinab   Click here for help

GtoPdb Ligand ID: 10058

Synonyms: APD-371 | APD371 | compound 6 [PMID: 29259753]
PDB Ligand
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) .
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
10809 olorinab
Synonyms Click here for help
APD-371 | APD371 | compound 6 [PMID: 29259753]
Database Links Click here for help
Specialist databases
GPCRdb Ligand olorinab
Other databases
CAS Registry No. 1268881-20-4 (source: WHO INN record)
GtoPdb PubChem SID 375973246
PubChem CID 60164925
Search Google for chemical match using the InChIKey ACSQLTBPYZSGBA-GMXVVIOVSA-N
Search Google for chemicals with the same backbone ACSQLTBPYZSGBA
Search PubMed clinical trials olorinab
Search PubMed titles olorinab
Search PubMed titles/abstracts olorinab
UniChem Compound Search for chemical match using the InChIKey ACSQLTBPYZSGBA-GMXVVIOVSA-N
UniChem Connectivity Search for chemical match using the InChIKey ACSQLTBPYZSGBA-GMXVVIOVSA-N