desipramine   Click here for help

GtoPdb Ligand ID: 2399

Synonyms: EX-4355 | JB-8181 | Norpramin® | Pertrofane® | Treyzafagit®
Approved drug PDB Ligand
desipramine is an approved drug (FDA (no history prior to 1964))
Compound class: Synthetic organic
Comment: Desipramine is one of the tricyclic antidepressants.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 15.27
Molecular weight 266.18
XLogP 3.79
No. Lipinski's rules broken 0
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Canonical SMILES CNCCCN1c2ccccc2CCc2c1cccc2
Isomeric SMILES CNCCCN1c2ccccc2CCc2c1cccc2
InChI InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3
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Summary of Clinical Use Click here for help
Desipramine is used to treat major depressive disorder. The drug exerts a positive effect on mood in patients suffering from depression. Off-label uses include treatment of neuropathic pain, agitation and insomnia and attention-deficit hyperactivity disorder (ADHD).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The antidepressant effects of drugs such as desipramine are postulated to be due to an overall increase in serotonergic neurotransmission, via inhibition of SLC6A2 (norepinephrine transporter). Side effects may arise from activity at other targets such as the histamine H1 receptor, the α1-adrenergic receptor and muscarinic receptors.