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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2D Structure
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Physico-chemical Properties
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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
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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
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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.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04302870 Motor Neurone Disease - Systematic Multi-Arm Adaptive Randomised Trial Phase 2/Phase 3 Interventional University of Edinburgh Amantadine is one of the drugs being evaluated in the 'multi-arm' MND-SMART study as a therapeutic option for MND/ALS.