nortriptyline   Click here for help

GtoPdb Ligand ID: 2404

Synonyms: Aventyl® | nortriptyline hydrochloride | Pamelor®
Approved drug PDB Ligand
nortriptyline is an approved drug (FDA (1964))
Compound class: Synthetic organic
Comment: Nortriptyline is a second-generation tricyclic antidepressant (TCA).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: nortriptyline

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
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 Click here for help
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.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com