Drug/Small Molecule:
amantadine

2D structure

Overview

Generic Names: 1-aminoadamantane; Adamantamine; Adamantanamine; Adamantylamine; Amantadine Base; Amantadine HCL; Amantidine; Aminoadamantane
Trade Names: Endantadine; Gen-Amantadine; Mantadine; Pk-Merz; Symadine; Symmetrel
PharmGKB Accession Id: PA448360

Description

An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake. PubChem (source: Drug Bank)

Indication

For the chemoprophylaxis, prophylaxis, and treatment of signs and symptoms of infection caused by various strains of influenza A virus. Also for the treatment of parkinsonism and drug-induced extrapyramidal reactions. (source: Drug Bank)

ATC Therapeutic Category

  • N04BB:Adamantane derivatives

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

The mechanism of its antiparkinsonic effect is not fully understood, but it appears to be releasing dopamine from the nerve endings of the brain cells, together with stimulation of norepinephrine response. The antiviral mechanism seems to be unrelated. The drug interferes with a viral protein, M2 (an ion channel), which is needed for the viral particle to become "uncoated" once it is taken inside the cell by endocytosis. (source: Drug Bank)

Pharmacology

Amantadine is an antiviral drug which also acts as an antiparkinson agent, for which it is usually combined with L-DOPA when L-DOPA responses decline (probably due to tolerance). It is a derivate of adamantane, like a similar drug rimantadine. The mechanism of action of amantadine in the treatment of Parkinson's disease and drug-induced extrapyramidal reactions is not known. It has been shown to cause an increase in dopamine release in the animal brain, and does not possess anticholinergic activity. (source: Drug Bank)

Food Interactions

Avoid alcohol.
Take without regard to meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

No appreciable metabolism, although negligible amounts of an acetyl metabolite have been identified. (source: Drug Bank)

Protein Binding

Approximately 67% bound to plasma proteins over a concentration range of 0.1 to 2.0 µg/mL. (source: Drug Bank)

Absorption

Amantadine is well absorbed orally from the gastrointestinal tract. (source: Drug Bank)

Toxicity

Deaths have been reported from overdose with amantadine. The lowest reported acute lethal dose was 2 grams. Drug overdose has resulted in cardiac, respiratory, renal or central nervous system toxicity. Cardiac dysfunction includes arrhythmia, tachycardia and hypertension. Pulmonary edema and respiratory distress (including ARDS) have been reported. Renal dysfunction including increased BUN, decreased creatinine clearance and renal insufficiency can occur. Central nervous system effects that have been reported include insomnia, anxiety, aggressive behavior, hypertonia, hyperkinesia, tremor, confusion, disorientation, depersonalization, fear, delirium, hallucination, psychotic reactions, lethargy, somnolence and coma. Seizures may be exacerbated in patients with prior history of seizure disorders. Hyperthermia has also been observed in cases where a drug overdose has occurred. (source: Drug Bank)

Isomeric SMILES Code:

C1C2CC3CC1CC(C2)(C3)N (source: Drug Bank)

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
DRD1 Uncurated Annotation (source: Drug Bank)
DRD2 Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
bendroflumethiazide Uncurated Annotation The diuretic increases the adverse effects of amantadine (source: Drug Bank)
chlorothiazide Uncurated Annotation The diuretic increases the adverse effects of amantadine (source: Drug Bank)
cyclothiazide Uncurated Annotation The diuretic increases the adverse effects of amantadine (source: Drug Bank)
donepezil Uncurated Annotation Possible antagonism of action (source: Drug Bank)
galantamine Uncurated Annotation Possible antagonism of action (source: Drug Bank)
hydrochlorothiazide Uncurated Annotation The diuretic increases the adverse effects of amantadine (source: Drug Bank)
indapamide Uncurated Annotation The diuretic increases the adverse effects of amantadine (source: Drug Bank)
memantine Uncurated Annotation Increased risk of CNS adverse effects with this association (source: Drug Bank)
rivastigmine Uncurated Annotation Possible antagonism of action (source: Drug Bank)
triamterene Uncurated Annotation The diuretic increases the adverse effects of amantadine (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00915
ChEBI ID:
2618
KEGG Compound ID:
C06818
PubChem Compound ID:
2130
PubChem Substance ID:
9036

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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