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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
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
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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

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
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
NDF-RT N0000175542
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
WHO-ATC N04BB01
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
NDF-RT N0000175543
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
WHO-VATC QN04BB01
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
LIVERTOX 33
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
Code System Code Type Description
EPA CompTox
768-94-5
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
IUPHAR
4128
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
RXCUI
620
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY RxNorm
EVMPD
SUB05389MIG
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
MESH
D000547
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
INN
1816
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
CAS
768-94-5
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
PUBCHEM
2130
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
WIKIPEDIA
AMANTADINE
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
ChEMBL
CHEMBL660
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
HSDB
768-94-5
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
LactMed
768-94-5
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
NCI_THESAURUS
C61632
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
DRUG BANK
DB00915
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
ECHA (EC/EINECS)
212-201-2
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY
MERCK INDEX
M1638
Created by admin on Tue Mar 06 10:40:30 UTC 2018 , Edited by admin on Tue Mar 06 10:40:30 UTC 2018
PRIMARY Merck Index