nortriptyline   

GtoPdb Ligand ID: 2404

Synonyms: Aventyl® | nortriptyline hydrochloride | Pamelor®
nortriptyline is an approved drug (FDA (1964))
Compound class: Synthetic organic
Comment: Nortriptyline is a second-generation tricyclic antidepressant (TCA).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 12.03
Molecular weight 263.17
XLogP 4.69
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CNCCC=C1c2ccccc2CCc2c1cccc2
Isomeric SMILES CNCCC=C1c2ccccc2CCc2c1cccc2
InChI InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-11,20H,6,12-14H2,1H3
InChI Key PHVGLTMQBUFIQQ-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Primarily indicated for the treatment of major depressive disorder, but is also used in the treatment of chronic pain, irritable bowel syndrome, sleep disorders, diabetic neuropathy, agitation and insomnia, and for the prevention of migraine.
Mechanism Of Action and Pharmacodynamic Effects
The exact mechanism of action of nortriptyline is unknown. It exhibits activity as a serotonin and/or noradrenaline reuptake inhibitor at the neuronal membrane, and also has activity across several GPCR families, including α-adrenoceptors, serotonin 5-HT2 receptors, muscarinic acetylcholine receptors and the histamine H1 receptor, and it also blocks sodium channels.
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