trimipramine   Click here for help

GtoPdb Ligand ID: 7317

Synonyms: 7162 RP | IL-6001 | Surmontil®
Approved drug
trimipramine is an approved drug (FDA (1979))
Compound class: Synthetic organic
Comment: Trimipramine is a tricyclic antidepressant (TCA) with antidepressant, anxiolytic, antipsychotic and sedative effects. Trimipramine is a racemic compound of two enantiomers; (S)-trimipramine and (R)-trimipramine. We show the non-stereo structure to represent the mixture.
Marketed formulations may contain trimipramine maleate (PubChem CID 5282318).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 6.48
Molecular weight 294.21
XLogP 4.33
No. Lipinski's rules broken 0
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Canonical SMILES CN(CC(CN1c2ccccc2CCc2c1cccc2)C)C
Isomeric SMILES CN(CC(CN1c2ccccc2CCc2c1cccc2)C)C
InChI InChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3
Bioactivity Comments
Trimipramine 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 transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
SERT Primary target of this compound Hs Inhibitor Inhibition 6.8 pKi - 1
pKi 6.8 (Ki 1.49x10-7 M) [1]
NET Primary target of this compound Hs Inhibitor Inhibition 5.6 pKi - 1
pKi 5.6 (Ki 2.45x10-6 M) [1]
DAT Primary target of this compound Hs Inhibitor Inhibition 5.4 pKi - 1
pKi 5.4 (Ki 3.78x10-6 M) [1]