doxepin   Click here for help

GtoPdb Ligand ID: 1225

Synonyms: Deptran® | P-3693A | Sinequan®
Approved drug PDB Ligand
doxepin is an approved drug (FDA (1969))
Compound class: Synthetic organic
Comment: Doxepin inhibits the sodium-dependent noradrenaline transporter SLC6A2.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 12.47
Molecular weight 279.16
XLogP 3.99
No. Lipinski's rules broken 0
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Canonical SMILES CN(CCC=C1c2ccccc2OCc2c1cccc2)C
Isomeric SMILES CN(CC/C=C\1/c2ccccc2OCc2c1cccc2)C
InChI InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+
No information available.
Summary of Clinical Use Click here for help
Doxepin is a tricyclic antidepressant used in the treatment of major depressive disorder and anxiety. The drug's positive effects on mood are only observed in depressed patients. In very low doses doxepin may be used to treat insomnia, and is also used 'off-label' in the treatment of chronic urticaria and in pain management.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Although doxepin is known to inhibit the sodium-dependent noradrenaline transporter SLC6A2, its detailed mechanism of action is not fully resolved. For further details and explanation see the DrugBank link on the Summary tab..