Amantadine

Amantadine

Clinical data
Trade names	Symmetrel
AHFS/Drugs.com	Monograph
MedlinePlus	a682064
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N04BB01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	86–90%
Protein binding	67%
Metabolism	Minimal (mostly to acetyl metabolites)
Biological half-life	10–31 hours
Excretion	Urine
Identifiers
IUPAC name Adamantan-1-amine
Synonyms	1-Adamantylamine
CAS Number	768-94-5 Y
PubChem (CID)	2130
IUPHAR/BPS	4128
DrugBank	DB00915 Y
ChemSpider	2045 Y
UNII	BF4C9Z1J53 Y
KEGG	D07441 Y
ChEBI	CHEBI:2618 Y
ChEMBL	CHEMBL660 Y
ECHA InfoCard	100.011.092
Chemical and physical data
Formula	C10H17N
Molar mass	151.249 g/mol
3D model (Jmol)	Interactive image
SMILES NC13CC2CC(CC(C1)C2)C3
InChI InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2 Y Key:DKNWSYNQZKUICI-UHFFFAOYSA-N Y

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.

Amantadine is a weak antagonist of the NMDA-type glutamate receptor, increases dopamine release, and blocks dopamine reuptake. This makes it a weak therapy for Parkinson's disease. Although, as an antiparkinsonian, it can be used as monotherapy, or together with L-DOPA to treat L-DOPA-related motor fluctuations (i.e., shortening of L-DOPA duration of clinical effect, probably related to progressive neuronal loss) and L-DOPA-related dyskinesias (choreiform movements associated with long-term L-DOPA use, probably related to chronic pulsatile stimulation of dopamine receptors).