Amantadine

Amantadine
Clinical data
Trade names	Gocovri, Symadine, Symmetrel, others
Other names	1-Adamantylamine
AHFS/Drugs.com	Monograph
MedlinePlus	a682064
License data	US DailyMed: Amantadine;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	N04BB01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	86–90%
Protein binding	67%
Metabolism	Minimal (mostly to acetyl metabolites)
Elimination half-life	10–31 hours
Excretion	Urine
Identifiers
	IUPAC name Adamantan-1-amine;
CAS Number	768-94-5 ; as HCl: 665-66-7;
PubChem CID	2130; as HCl: 64150;
IUPHAR/BPS	4128;
DrugBank	DB00915 ; as HCl: DBSALT000203;
ChemSpider	2045 ; as HCl: 57724;
UNII	BF4C9Z1J53; as HCl: M6Q1EO9TD0;
KEGG	D07441 ; as HCl: D00777 ;
ChEBI	CHEBI:2618 ; as HCl: CHEBI:2619;
ChEMBL	ChEMBL660 ; as HCl: ChEMBL1569;
CompTox Dashboard (EPA)	DTXSID8022117 ;
ECHA InfoCard	100.011.092
Chemical and physical data
Formula	C10H17N
Molar mass	151.253 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	180 °C (356 °F)
	SMILES C1C2CC3CC1CC(C2)(C3)N;
	InChI InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2 ; Key:DKNWSYNQZKUICI-UHFFFAOYSA-N ;
	(verify)

Amantadine, sold under the brand name Gocovri among others, is a medication used to treat dyskinesia associated with parkinsonism and influenza caused by type A influenzavirus, though its use for the latter is no longer recommended because of widespread drug resistance. It acts as a nicotinic antagonist, dopamine agonist, and noncompetitive NMDA antagonist. The antiviral mechanism of action is antagonism of the influenzavirus A M2 proton channel, which prevents endosomal escape (i.e., the release of viral genetic material into the host cytoplasm).

Amantadine was first used for the treatment of influenza A. After antiviral properties were initially reported in 1963, amantadine received approval for prophylaxis against the influenza virus A in 1976. In 1973, the Food and Drug Administration (FDA) approved amantadine for use in the treatment of Parkinson's disease. In 2017, the extended release formulation was approved for use in the treatment of levodopa-induced dyskinesia.

Amantadine has a mild side-effect profile. Common neurological side effects include drowsiness, light-headedness, dizziness, and confusion. Because of its effects on the central nervous system, it should only be combined cautiously with additional CNS stimulants or anticholinergic drugs. Amantadine is contraindicated in persons with end stage kidney disease, given that the drug is cleared by the kidneys. It should also be taken with caution by those with enlarged prostates or glaucoma, because of its anticholinergic effects.

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