amantadine   Click here for help

GtoPdb Ligand ID: 4128

Synonyms: ADS-5102 | Gocovri® | Symadine® | Symmetrel®
Approved drug
amantadine is an approved drug (FDA (1966))
Compound class: Synthetic organic
Comment: Chemically amantadine has an adamantane backbone with an amino group substituted at one of the four methyne positions. Clinically it has antiviral (blocking the viral M2 proton channel) and antiparkinsonian actions.
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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
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 0
Topological polar surface area 26.02
Molecular weight 151.14
XLogP 2.31
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 NC12CC3CC(C2)CC(C1)C3
Isomeric SMILES NC12CC3CC(C2)CC(C1)C3
InChI InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2
InChI Key DKNWSYNQZKUICI-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Amantadine has historically been used as an antiviral agent to treat influenza, but as the flu virus has become resistant to amantadine this use is no longer recommended.
In August 2017, the US FDA approved Gocovri®, an extended release, high dose formulation of amantadine for the treatment of dyskinesia in Parkinson's disease (PD), for patients already receiving levodopa-based therapy, irrespective of whether or not they are receiving concomitant dopaminergic medications. Clinical trial results showed that Gocovri® reduced both dyskinesia and 'off' time' in levodopa treated PD patients [2]. This first PD approval was followed in February 2018 with FDA approval of Osmolex ER (another extended release formulation of amantadine) for the treatment of PD and for the treatment of drug-induced extrapyramidal reactions. In Europe amantadine is not approved at the EMA level, but is/has been approved in a number of national jurisdictions including the UK, France, Italy, Greece and the Netherlands.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Amantadine's MMOA in the treatment of Parkinson's symptoms arises from its multifunctional activity. These actions include, antagonism of the NMDA type glutamate receptor, stimulation of increased dopamine release, and inhibition of dopamine reuptake.