imipramine   Click here for help

GtoPdb Ligand ID: 357

Synonyms: imidobenzyle | Tofranil®
Approved drug PDB Ligand
imipramine is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Imipramine is a tricyclic antidepressant (TCA).
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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 280.19
XLogP 4.03
No. Lipinski's rules broken 0
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Canonical SMILES CN(CCCN1c2ccccc2CCc2c1cccc2)C
Isomeric SMILES CN(CCCN1c2ccccc2CCc2c1cccc2)C
InChI InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
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Summary of Clinical Use Click here for help
Imipramine is used to treat major depressive disorder. The drug is also used to treat panic disorders, ADHD, eating disorders, acute depressive episodes in bipolar disorder and schizophrenia, and neuralgic pain.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Imipramine inhibits reuptake of serotonin and norepinephrine by inhibiting the sodium-dependent transporters responsible for their trans-membrane transport (SLC6A4 and SLC6A2 respectively).