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Details

Stereochemistry ACHIRAL
Molecular Formula 2C10H17N.H2O4S
Molecular Weight 400.5777
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMANTADINE SULFATE

SMILES

C1C2CC3CC1CC(C2)(C3)N.C1C2CC3CC1CC(C2)(C3)N.OS(=O)(=O)O

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 98.0796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H17N
Molecular Weight 151.2491
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

540518400000
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

540518400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
Visual hallucinations and delirium during treatment with amantadine (Symmetrel).
1975 May
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
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
Activities of antifolate, antiviral, and other drugs in an immunosuppressed rat model of Pneumocystis carinii pneumonia.
1992 Sep
Amantadine-induced multiple spike waves on an electroencephalogram of a schizophrenic patient.
2000 Jan
The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches.
2001
[The use of amantadine sulfate in combined therapy of Parkinson's disease].
2002
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
Amantadine in Huntington's disease: open-label video-blinded study.
2002 Sep
Huntington's disease: a randomized, controlled trial using the NMDA-antagonist amantadine.
2002 Sep 10
NMDA receptor antagonists to characterize rat renal organic cation transporter function.
2002 Sep 27
[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
Heterocyclic rimantadine analogues with antiviral activity.
2003 Dec 1
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
Mirtazapine in L-dopa-induced dyskinesias.
2003 Jul-Aug
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
Livedo reticularis induced by amantadine.
2003 Sep
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
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
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
[Comparative study of neurophysiological effects of adamantane derivatives in the experimental parkinsonism model].
2004 Mar-Apr
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
Amantadine for levodopa-induced choreic dyskinesia in compound heterozygotes for GCH1 mutations.
2004 Oct
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
Combined blockade of AMPA and NMDA glutamate receptors reduces levodopa-induced motor complications in animal models of PD.
2005 Dec
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
Low-dose levodopa therapy in Japanese patients with Parkinson's disease: a retrospective study.
2005 Sep
Determination of serum amantadine by liquid chromatography-tandem mass spectrometry.
2005 Sep
Comparative anti-tumor efficacy of two orally administered platinum(IV) drugs in nude mice bearing human tumor xenografts.
2006 Feb
Platinum(IV) complex with adamantylamine overcomes intrinsic resistance to cisplatin in ovarian cancer cells.
2006 Jul
Interferon signal transduction of biphenyl dimethyl dicarboxylate/amantadine and anti-HBV activity in HepG2 2.2.15.
2006 May
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
Patents

Sample Use Guides

Uncomplicated Influenza A Virus Illness:
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:42:45 UTC 2021
Edited
by admin
on Sat Jun 26 07:42:45 UTC 2021
Record UNII
9921T5P019
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
NCI_THESAURUS C93038
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
Code System Code Type Description
FDA UNII
9921T5P019
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
EVMPD
SUB00423MIG
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
RXCUI
621
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY RxNorm
PUBCHEM
124108
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
DRUG BANK
DBSALT000830
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
MERCK INDEX
M1638
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C90781
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
CAS
31377-23-8
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
EVMPD
SUB78132
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
250-604-5
Created by admin on Sat Jun 26 07:42:45 UTC 2021 , Edited by admin on Sat Jun 26 07:42:45 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY