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Details

Stereochemistry ACHIRAL
Molecular Formula 2C10H17N.H2O4S
Molecular Weight 400.576
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMANTADINE SULFATE

SMILES

OS(O)(=O)=O.NC12CC3CC(CC(C3)C1)C2.NC45CC6CC(CC(C6)C4)C5

InChI

InChIKey=MYWTWSQFJLXGGQ-UHFFFAOYSA-N
InChI=1S/2C10H17N.H2O4S/c2*11-10-4-7-1-8(5-10)3-9(2-7)6-10;1-5(2,3)4/h2*7-9H,1-6,11H2;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Blockade of the central effects of d-amphetamine by amantadine. II.
1975 May
Visual hallucinations and delirium during treatment with amantadine (Symmetrel).
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
Amantadine as N-methyl-D-aspartic acid receptor antagonist: new possibilities for therapeutic applications?
1992
A trigger for Tourette's syndrome.
1992 Mar
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Neuroleptic malignant syndrome induced by haloperidol following traumatic brain injury.
1999 Dec
Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus A activity relationship study using a combination of NMR spectroscopy and molecular modeling.
1999 Dec 20
A novel approach to antiviral therapy for influenza.
1999 Nov
Amantadine in the treatment of cocaine-dependent patients with severe withdrawal symptoms.
2000 Dec
Cerebellar Ataxia.
2000 May
Comparison of central nervous system adverse effects of amantadine and rimantadine used as sequential prophylaxis of influenza A in elderly nursing home patients.
2000 May 22
Beneficial effects of amantadine on L-dopa-induced dyskinesias in Parkinson's disease.
2000 Sep
Synthesis, structure and tumour necrosis factor-alpha production-enhancing properties of novel adamantylamino heterocyclic derivatives.
2001 Apr-Jun
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.
2001 Jan
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
An unusual case of chronic neuropathic pain responds to an optimum frequency of intravenous ketamine infusions.
2001 May
An MCASE approach to the search of a cure for Parkinson's Disease.
2002 Apr 2
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
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
Spiro[pyrrolidine-2,2'-adamantanes]: synthesis, anti-influenza virus activity and conformational properties.
2003 May 19
Livedo reticularis induced by amantadine.
2003 Sep
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
Effects of perioperative oral amantadine on postoperative pain and morphine consumption in patients after radical prostatectomy: results of a preliminary study.
2004 Jan
Liquid chromatographic determination of 1-adamantanamine and 2-adamantanamine in human plasma after pre-column derivatization with o-phthalaldehyde and 1-thio-beta-D-glucose.
2004 Jan 25
Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for the treatment of hepatitis C.
2004 May
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
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
Preclinical anti-tumor activity of a new oral platinum(IV) drug LA-12.
2005 Jul
Pharmacological validation of a mouse model of l-DOPA-induced dyskinesia.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Amantadine reduces the duration of levodopa-induced dyskinesia: a randomized, double-blind, placebo-controlled study.
2005 Nov
Determination of serum amantadine by liquid chromatography-tandem mass spectrometry.
2005 Sep
Glutamate receptors in neuroinflammatory demyelinating disease.
2006
Comparative anti-tumor efficacy of two orally administered platinum(IV) drugs in nude mice bearing human tumor xenografts.
2006 Feb
A novel soluble mimic of the glycolipid, globotriaosyl ceramide inhibits HIV infection.
2006 Feb 14
The pharmacology of aminoadamantane nitrates.
2006 Jul
Hiccups associated with dopamine agonists in Parkinson disease.
2006 Mar 14
Simultaneous liquid chromatographic assay of amantadine and its four related compounds in phosphate-buffered saline using 4-fluoro-7-nitro-2,1,3-benzoxadiazole as a fluorescent derivatization reagent.
2006 May
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
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:42:12 UTC 2019
Edited
by admin
on Tue Oct 22 00:42:12 UTC 2019
Record UNII
9921T5P019
Record Status Validated (UNII)
Record Version
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Name Type Language
AMANTADINE SULFATE
MART.   MI   WHO-DD  
Common Name English
AMANTADINE SULPHATE (2:1)
Common Name English
1-AMINOADAMANTANE SULPHATE
Systematic Name English
1-ADAMANTANAMINE SULPHATE SALT (2:1)
Common Name English
1-ADAMANTANAMINE SULFATE
Systematic Name English
1-AMINOADAMANTANE SULFATE
Systematic Name English
AMANTADINE SULFATE [WHO-DD]
Common Name English
AMANTADINE SULFATE [MART.]
Common Name English
AMANTADINE SULFATE (2:1)
Common Name English
AMANTADINE SULPHATE
Common Name English
AMANTADINE HEMISULFATE
Common Name English
AMANTADINE SULFATE [MI]
Common Name English
TRICYCLO(3.3.1.19(SUP 3,7))DECAN-1-AMINE
Common Name English
1-ADAMANTANAMINE SULPHATE
Systematic Name English
1-ADAMANTANAMINE SULFATE SALT (2:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
NCI_THESAURUS C93038
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
Code System Code Type Description
EVMPD
SUB00423MIG
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY
RXCUI
621
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY RxNorm
PUBCHEM
124108
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY
MERCK INDEX
M1638
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C90781
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY
CAS
31377-23-8
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY
EVMPD
SUB78132
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY
ECHA (EC/EINECS)
250-604-5
Created by admin on Tue Oct 22 00:42:12 UTC 2019 , Edited by admin on Tue Oct 22 00:42:12 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY