U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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Details

Stereochemistry ACHIRAL
Molecular Formula C10H17N
Molecular Weight 151.2487
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMANTADINE

SMILES

NC12CC3CC(CC(C3)C1)C2

InChI

InChIKey=DKNWSYNQZKUICI-UHFFFAOYSA-N
InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2

HIDE SMILES / InChI
Amantadine hydrochloride has pharmacological actions as both an anti-Parkinson and an antiviral drug. The mechanism by which amantadine exerts its antiviral activity is not clearly understood. It appears to mainly prevent the release of infectious viral nucleic acid into the host cell by interfering with the function of the transmembrane domain of the viral M2 protein. In certain cases, amantadine is also known to prevent virus assembly during virus replication. It does not appear to interfere with the immunogenicity of inactivated influenza A virus vaccine. The mechanism of action of amantadine in the treatment of Parkinson's disease and drug-induced extrapyramidal reactions is not known. Data from earlier animal studies suggest that amantadine hydrochloride may have direct and indirect effects on dopamine neurons. More recent studies have demonstrated that amantadine is a weak, non-competitive NMDA receptor antagonist (K1 = 10µM). Although amantadine has not been shown to possess direct anticholinergic activity in animal studies, clinically, it exhibits anticholinergic-like side effects such as dry mouth, urinary retention, and constipation. Amantadine was approved by the FDA in 1966 as a prophylactic agent against Asian influenza, and eventually received approval for the treatment of influenza virus A in adults. In 1969, it was also discovered by accident to help reduce symptoms of Parkinson's disease, drug-induced extrapyramidal syndromes, and akathisia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MANTADINE HYDROCHLORIDE

Approved Use

Amantadine Hydrochloride Capsules, USP are indicated for the prophylaxis and treatment of signs and symptoms of infection caused by various strains of influenza A virus. Amantadine Hydrochloride Capsules, USP are also indicated in the treatment of parkinsonism and drug-induced extrapyramidal reactions.

Launch Date

1987
Primary
MANTADINE HYDROCHLORIDE

Approved Use

Amantadine Hydrochloride Capsules, USP are indicated for the prophylaxis and treatment of signs and symptoms of infection caused by various strains of influenza A virus. Amantadine Hydrochloride Capsules, USP are also indicated in the treatment of parkinsonism and drug-induced extrapyramidal reactions.

Launch Date

1987
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.24 μg/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMANTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
636.2 ng/mL
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMANTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6413.6 ng × h/mL
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMANTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.7 h
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMANTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
33%
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMANTADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
yes [Ki 111.8 uM]
yes [Ki 1167 uM]
yes [Ki 236 uM]
yes [Ki 284 uM]
yes [Ki >1000 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Blockade of the central effects of d-amphetamine by amantadine. II.
1975 May
Efficacy of 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide against influenza virus infections in mice.
1975 May
Differential inhibitory effects of sulfated polysaccharides and polymers on the replication of various myxoviruses and retroviruses, depending on the composition of the target amino acid sequences of the viral envelope glycoproteins.
1991 Dec
Neurotoxicity of chlorpromazine and modulation by amantadine as a function of mouse strain.
1991 Fall
A trigger for Tourette's syndrome.
1992 Mar
Medication-induced hallucination and cerebral blood flow in Parkinson's disease.
1999 May
Amantadine for levodopa-induced dyskinesias: a 1-year follow-up study.
1999 Nov
[Amantadine for the treatment of levodopa dyskinesias in Parkinson's disease].
2000
Amantadine-induced multiple spike waves on an electroencephalogram of a schizophrenic patient.
2000 Jan
The effect of amantadine on levodopa-induced dyskinesias in Parkinson's disease: a double-blind, placebo-controlled study.
2000 Mar-Apr
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.
2001 Jan
Amantadine-induced cortical myoclonus.
2001 Jan 23
A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1.
2001 Jun
[L-dopa-induced movement disorders in Parkinson disease. Amantadine improves dyskinesia].
2001 May 28
Synthesis of valproic acid amides of a melatonin derivative, a piracetam and amantadine for biological tests.
2001 Oct
[The use of amantadine sulfate in combined therapy of Parkinson's disease].
2002
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.
2002 Oct
Amantadine in Huntington's disease: open-label video-blinded study.
2002 Sep
Synthesis and antioxidant activity evaluation of novel antiparkinsonian agents, aminoadamantane derivatives of nitroxyl free radical.
2003 Aug 5
An artist's view of drug-induced hallucinosis.
2003 Jul
Synthesis of 1-boraadamantaneamine derivatives with selective astrocyte vs C6 glioma antiproliferative activity. A novel class of anti-hepatitis C agents with potential to bind CD81.
2003 Jul 3
Noncompetitive antagonist binding sites in the torpedo nicotinic acetylcholine receptor ion channel. Structure-activity relationship studies using adamantane derivatives.
2003 Jun 24
Risperidone treatment of motor restlessness following anoxic brain injury.
2003 Mar
Spiro[pyrrolidine-2,2'-adamantanes]: synthesis, anti-influenza virus activity and conformational properties.
2003 May 19
Peginterferon alpha-2b plus ribavirin with or without amantadine [correction of amantidine] for the treatment of non-responders to standard interferon and ribavirin.
2004 Aug
Bitterness evaluation of medicines for pediatric use by a taste sensor.
2004 Aug
Long term motor complications of levodopa: clinical features, mechanisms, and management strategies.
2004 Aug
New platinum(IV) complex with adamantylamine ligand as a promising anti-cancer drug: comparison of in vitro cytotoxic potential towards A2780/cisR cisplatin-resistant cell line within homologous series of platinum(IV) complexes.
2004 Jun
Adverse effects of amantadine and oseltamivir used during respiratory outbreaks in a center for developmentally disabled adults.
2004 Nov
Prevention of influenza in the general population.
2004 Nov 9
Amantadine for levodopa-induced choreic dyskinesia in compound heterozygotes for GCH1 mutations.
2004 Oct
High effectiveness of platinum(IV) complex with adamantylamine in overcoming resistance to cisplatin and suppressing proliferation of ovarian cancer cells in vitro.
2005 Feb 1
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Determination of serum amantadine by liquid chromatography-tandem mass spectrometry.
2005 Sep
Glutamate receptors in neuroinflammatory demyelinating disease.
2006
[Cytosine demethylation in the tyrosine hydroxylase gene promoter in the hypothalamus cells of the rat brain under the action of an aminoadamantane derivative Ladasten].
2006 Jul
The pharmacology of aminoadamantane nitrates.
2006 Jul
Pharmacological characterization of psychosis-like behavior in the MPTP-lesioned nonhuman primate model of Parkinson's disease.
2006 Nov
Behavioral effects of aminoadamantane class NMDA receptor antagonists on schedule-induced alcohol and self-administration of water in mice.
2006 Sep
Identification of genes associated with cisplatin resistance in human oral squamous cell carcinoma cell line.
2006 Sep 15
Modulation of L-DOPA-induced abnormal involuntary movements by clinically tested compounds: further validation of the rat dyskinesia model.
2007 Apr 16
19F NMR detection of the complex between amantadine and the receptor portion of the influenza A M2 ion channel in DPC micelles.
2007 Jul 15
Patents

Sample Use Guides

Uncomplicated Influenza A Virus Illness: Adult: 200 mg; two 100 mg capsules as a single daily dose. The daily dosage may be split into one capsule of 100 mg twice a day. In persons 65 years of age or older, the daily dosage is 100 mg. Parkinsonism: Adult: is 100 mg twice a day when used alone. Amantadine Hydrochloride Capsules have an onset of action usually within 48 hours. The initial dose is 100 mg daily for patients with serious associated medical illnesses or who are receiving high doses of other antiparkinson drugs. After one to several weeks at 100 mg once daily, the dose may be increased to 100 mg twice daily, if necessary.
Route of Administration: Oral
Amantadine markedly inhibited the proliferation of HepG2 and SMMC‑7721 cells in a dose‑ and time‑dependent manner and arrested the cell cycle at the G0/G1 phase
Name Type Language
AMANTADINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
NSC-341865
Preferred Name English
GOCOVRI
Brand Name English
AMANTADINE [MI]
Common Name English
AMANTADINE [MART.]
Common Name English
AMANTADINE [VANDF]
Common Name English
ADAMANTAN-1-AMINE
Systematic Name English
amantadine [INN]
Common Name English
AMANTIDINE
Common Name English
Amantadine [WHO-DD]
Common Name English
AMANTADINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C93038
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
NCI_THESAURUS C281
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
NDF-RT N0000175542
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
NCI_THESAURUS C38149
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
WHO-ATC N04BB01
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
NDF-RT N0000175543
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
WHO-VATC QN04BB01
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
LIVERTOX NBK547954
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
Code System Code Type Description
FDA UNII
BF4C9Z1J53
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PRIMARY
EPA CompTox
DTXSID8022117
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PRIMARY
IUPHAR
4128
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PRIMARY
NSC
341865
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PRIMARY
RXCUI
620
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PRIMARY RxNorm
DRUG CENTRAL
144
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PRIMARY
EVMPD
SUB05389MIG
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PRIMARY
MESH
D000547
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PRIMARY
SMS_ID
100000087646
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PRIMARY
INN
1816
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PRIMARY
CHEBI
2618
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PRIMARY
CAS
768-94-5
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PRIMARY
PUBCHEM
2130
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
PRIMARY
LACTMED
Amantadine
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
PRIMARY
DAILYMED
BF4C9Z1J53
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
PRIMARY
WIKIPEDIA
AMANTADINE
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PRIMARY
ChEMBL
CHEMBL660
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PRIMARY
HSDB
3202
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PRIMARY
NCI_THESAURUS
C61632
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PRIMARY
DRUG BANK
DB00915
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
PRIMARY
ECHA (EC/EINECS)
212-201-2
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PRIMARY
MERCK INDEX
m1638
Created by admin on Mon Mar 31 17:51:43 GMT 2025 , Edited by admin on Mon Mar 31 17:51:43 GMT 2025
PRIMARY Merck Index