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Amantadine (trade name Symmetrel, by Endo Pharmaceuticals ) is a medication that has U.S. Food and Drug Administration approval for use both as an antiviral and an antiparkinsonian medication. It is the organic compound 1-adamantylamine or 1-aminoadamantane, meaning it consists of an adamantane backbone that has an amino group substituted at one of the four methyne positions. Rimantadine is a closely related derivative of adamantane with similar biological properties.
Apart from medical uses, this compound is useful as a building block in organic synthesis, allowing the insertion of an adamantyl group.
According to the U.S. Centers for Disease Control and Prevention (CDC) 100% of seasonal H3N2 and 2009 pandemic flu samples tested showed resistance to adamantanes, and amantadine is no longer recommended for treatment of influenza in the United States. Additionally, its effectiveness as an antiparkinsonian drug is undetermined, with a 2003 Cochrane Review concluding that there was insufficient evidence in support of or against its efficacy and safety.
1 Medical uses
1.1 Parkinson’s disease
1.3 Fatigue in multiple sclerosis
2 Adverse effects
3 Mechanism of action
3.2 Parkinson’s disease
5 Veterinary misuse
6 See also
Amantadine is used to treat Parkinson’s disease, as well as parkinsonism syndromes.
An extended release formulation is used to treat dyskinesia, a side effect of levodopa which is taken by people who have Parkinsons.
Amantadine is no longer recommended for treatment of influenza A infection. For the 2008/2009 flu season, the CDC found that 100% of seasonal H3N2 and 2009 pandemic flu samples tested have shown resistance to adamantanes.
Fatigue in multiple sclerosis
Amantadine also seems to have moderate effects on multiple sclerosis (MS) related fatigue.
Amantadine has been associated with several central nervous system (CNS) side effects, likely due to amantadine’s dopaminergic and adrenergic activity, and to a lesser extent, its activity as an anticholinergic. CNS side effects include nervousness, anxiety, agitation, insomnia, difficulty in concentrating, and exacerbations of pre-existing seizure disorders and psychiatric symptoms in patients with schizophrenia or Parkinson’s disease. The usefulness of amantadine as an anti-parkinsonian drug is somewhat limited by the need to screen patients for a history of seizures and psychiatric symptoms.
Rare cases of severe skin rashes, such as Stevens-Johnson syndrome,
Livedo reticularis is a possible side effect of amantadine use for Parkinson’s disease.
Mechanism of action
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The mechanisms for amantadine’s antiviral and antiparkinsonian effects are unrelated. The mechanism of amantadine’s antiviral activity involves interference with the viral protein, M 2, a proton channel.
Influenza B strains possess a structurally distinct M 2 channel with channel-facing side chains that fully obstruct the channel vis-à-vis binding of adamantine-class channel inhibitors, while still allowing proton flow and channel function to occur; this constriction in the channels is responsible for the ineffectiveness of this drug and rimantadine towards all circulating Influenza B strains.
Amantadine is a weak antagonist of the NMDA-type glutamate receptor, increases dopamine release, and blocks dopamine reuptake. as well as an anticholinergic, specifically a nicotinic alpha-7 antagonist like the similar pharmaceutical memantine.
In 2004, it was discovered that amantadine and memantine bind to and act as agonists of the σ 1 receptor (K i = 7.44 µM and 2.60 µM, respectively), and that activation of the σ 1 receptor is involved in the dopaminergic effects of amantadine at therapeutically relevant concentrations.
Amantadine was approved by the U.S. Food and Drug Administration in October 1966 as a prophylactic agent against Asian influenza, and eventually received approval for the treatment of influenzavirus A in adults. In 1969, the drug was also discovered by accident upon trying to help reduce symptoms of Parkinson’s disease, drug-induced extrapyramidal syndromes, and akathisia.
In 2017, the U.S. Food and Drug Administration approved the use of amantadine in an extended release formulation developed by Adamas Pharma for the treatment of dyskinesia, an adverse effect of levodopa, that people with Parkinson’s experience.
In 2005, Chinese poultry farmers were reported to have used amantadine to protect birds against avian influenza.
On September 23, 2015, the US Food and Drug Administration announced the recall of Dingo Chip Twists “Chicken in the Middle” dog treats because the product has the potential to be contaminated with amantadine.
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