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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H17N
Molecular Weight 151.2487
Optical Activity UNSPECIFIED
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

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MANTADINE HYDROCHLORIDE
Primary
MANTADINE HYDROCHLORIDE
PubMed

PubMed

TitleDatePubMed
Antagonistic effect of cyproheptadine on neuroleptic-induced catalepsy.
1975 Jan-Feb
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
Successful treatment of levodopa-induced neuroleptic malignant syndrome (NMS) and disseminated intravascular coagulation (DIC) in a patient with Parkinson's disease.
1992 Nov
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
[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
Cerebellar Ataxia.
2000 May
Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease.
2000 Sep
Beneficial effects of amantadine on L-dopa-induced dyskinesias in Parkinson's disease.
2000 Sep
The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches.
2001
Synthesis, structure and tumour necrosis factor-alpha production-enhancing properties of novel adamantylamino heterocyclic derivatives.
2001 Apr-Jun
Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus-identification of aminoadamantane derivatives bearing two pharmacophoric amine groups.
2001 Aug 20
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
Synthesis and pharmacological evaluation of potent and enantioselective sigma 1, and sigma 2 ligands.
2001 Mar
[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
Electrophoretic behavior of adamantane derivatives possessing antiviral activity and their determination by capillary zone electrophoresis with indirect detection.
2002 Jan
Chiral separation of enantiomeric 1,2-diamines using molecular imprinting method and selectivity enhancement by addition of achiral primary amines into eluents.
2002 Jan
Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice.
2002 Jan-Feb
A screening trial of amantadine as a medication for cocaine dependence.
2002 May 1
Huntington's disease: a randomized, controlled trial using the NMDA-antagonist amantadine.
2002 Sep 10
[Cortico-basal degeneration: the rare form of tau protein disease].
2003
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
Effects of perioperative oral amantadine on postoperative pain and morphine consumption in patients after radical prostatectomy: results of a preliminary study.
2004 Jan
Levetiracetam potentiates the antidyskinetic action of amantadine in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-lesioned primate model of Parkinson's disease.
2004 Jul
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
Treatment of interferon non-responsive chronic hepatitis C with triple therapy with interferon, ribavirin, and amantidine can be encouraging.
2004 Mar
Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for the treatment of hepatitis C.
2004 May
Prevention of influenza in the general population.
2004 Nov 9
The potential anti-hBV effect of amantadine in combination with ursodeoxycholic acid and biphenyl dimethyl dicarboxylate in hepG2 2.2.15 cells.
2005 Apr
Site-isolated porphyrin catalysts in imprinted polymers.
2005 Aug 19
Preclinical anti-tumor activity of a new oral platinum(IV) drug LA-12.
2005 Jul
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
Hiccups associated with dopamine agonists in Parkinson disease.
2006 Mar 14
Interferon signal transduction of biphenyl dimethyl dicarboxylate/amantadine and anti-HBV activity in HepG2 2.2.15.
2006 May
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

In Vivo Use Guide
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
In Vitro Use Guide
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
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
NSC-341865
Code 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 Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
NCI_THESAURUS C281
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
NDF-RT N0000175542
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
NCI_THESAURUS C38149
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
WHO-ATC N04BB01
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
NDF-RT N0000175543
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
WHO-VATC QN04BB01
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
LIVERTOX 33
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
Code System Code Type Description
EPA CompTox
768-94-5
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
IUPHAR
4128
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
RXCUI
620
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY RxNorm
EVMPD
SUB05389MIG
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
MESH
D000547
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
INN
1816
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
CAS
768-94-5
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
PUBCHEM
2130
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
WIKIPEDIA
AMANTADINE
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
ChEMBL
CHEMBL660
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
HSDB
768-94-5
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
LactMed
768-94-5
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
NCI_THESAURUS
C61632
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
DRUG BANK
DB00915
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
ECHA (EC/EINECS)
212-201-2
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY
MERCK INDEX
M1638
Created by admin on Mon Oct 21 19:51:25 UTC 2019 , Edited by admin on Mon Oct 21 19:51:25 UTC 2019
PRIMARY Merck Index