opipramol   Click here for help

GtoPdb Ligand ID: 11247

Synonyms: Insidon®
Approved drug
opipramol is an approved drug
Compound class: Synthetic organic
Comment: Opipramol is an atypical tricyclic antidepressant (TCA) [3]. It acts primarily as a sigma (σ) receptor agonist. Weak antiviral activity of opipramol dihydrochloride against SARS-CoV-2 (in Vero E6 cells; EC50 5 μM) was reported by Touret et al. [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 29.95
Molecular weight 363.23
XLogP 3.25
No. Lipinski's rules broken 0
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Canonical SMILES OCCN1CCN(CC1)CCCN1c2ccccc2C=Cc2c1cccc2
Isomeric SMILES OCCN1CCN(CC1)CCCN1c2ccccc2C=Cc2c1cccc2
InChI InChI=1S/C23H29N3O/c27-19-18-25-16-14-24(15-17-25)12-5-13-26-22-8-3-1-6-20(22)10-11-21-7-2-4-9-23(21)26/h1-4,6-11,27H,5,12-19H2
Bioactivity Comments
Opipramol is one of a number of drugs that are cationic amphiphilic in nature, for which anti-SARS-CoV-2 activity has been identified in drug repurposing screens. Tummino et al. (2021; bioRxiv preprint PMID: 33791693 target="_blank") suggest that this antiviral activity is most likely a result of the drug promoting phospholipidosis via disruption of lipid homeostasis.
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
sigma non-opioid intracellular receptor 1 Cp Agonist Agonist 9.7 pKi - 2
pKi 9.7 (Ki 2x10-10 M) [2]