|ATC code||N04BB01 (WHO)|
|Metabolism||Minimal (mostly to acetyl metabolites)|
|Biological half-life||10–31 hours|
Systematic (IUPAC) name: Adamantan-1-amine
|Chemical and physical data|
|Molar mass||151.249 g/mol|
|3D model (Jmol)||Interactive image|
Amantadine (trade name Symmetrel, by Endo Pharmaceuticals) is a drug that has U.S. Food and Drug Administration approval for use both as an antiviral and an antiparkinsonian drug. 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.