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
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
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15800186 |
10.0 µM [Ki] | ||
Target ID: CHEMBL1932894 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18669647 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | MANTADINE HYDROCHLORIDE Approved UseAmantadine 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 Date1987 |
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Primary | MANTADINE HYDROCHLORIDE Approved UseAmantadine 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 Date1987 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18074029 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6413.6 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18074029 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18074029 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
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Blockade of the central effects of d-amphetamine by amantadine. II. | 1975 May |
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Efficacy of 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide against influenza virus infections in mice. | 1975 May |
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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 |
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Neurotoxicity of chlorpromazine and modulation by amantadine as a function of mouse strain. | 1991 Fall |
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A trigger for Tourette's syndrome. | 1992 Mar |
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Medication-induced hallucination and cerebral blood flow in Parkinson's disease. | 1999 May |
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Amantadine for levodopa-induced dyskinesias: a 1-year follow-up study. | 1999 Nov |
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[Amantadine for the treatment of levodopa dyskinesias in Parkinson's disease]. | 2000 |
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Amantadine-induced multiple spike waves on an electroencephalogram of a schizophrenic patient. | 2000 Jan |
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The effect of amantadine on levodopa-induced dyskinesias in Parkinson's disease: a double-blind, placebo-controlled study. | 2000 Mar-Apr |
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Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior. | 2001 Jan |
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Amantadine-induced cortical myoclonus. | 2001 Jan 23 |
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A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1. | 2001 Jun |
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[L-dopa-induced movement disorders in Parkinson disease. Amantadine improves dyskinesia]. | 2001 May 28 |
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Synthesis of valproic acid amides of a melatonin derivative, a piracetam and amantadine for biological tests. | 2001 Oct |
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[The use of amantadine sulfate in combined therapy of Parkinson's disease]. | 2002 |
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Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds. | 2002 Oct |
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Amantadine in Huntington's disease: open-label video-blinded study. | 2002 Sep |
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Synthesis and antioxidant activity evaluation of novel antiparkinsonian agents, aminoadamantane derivatives of nitroxyl free radical. | 2003 Aug 5 |
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An artist's view of drug-induced hallucinosis. | 2003 Jul |
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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 |
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Noncompetitive antagonist binding sites in the torpedo nicotinic acetylcholine receptor ion channel. Structure-activity relationship studies using adamantane derivatives. | 2003 Jun 24 |
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Risperidone treatment of motor restlessness following anoxic brain injury. | 2003 Mar |
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Spiro[pyrrolidine-2,2'-adamantanes]: synthesis, anti-influenza virus activity and conformational properties. | 2003 May 19 |
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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 |
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Bitterness evaluation of medicines for pediatric use by a taste sensor. | 2004 Aug |
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Long term motor complications of levodopa: clinical features, mechanisms, and management strategies. | 2004 Aug |
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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 |
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Adverse effects of amantadine and oseltamivir used during respiratory outbreaks in a center for developmentally disabled adults. | 2004 Nov |
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Prevention of influenza in the general population. | 2004 Nov 9 |
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Amantadine for levodopa-induced choreic dyskinesia in compound heterozygotes for GCH1 mutations. | 2004 Oct |
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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 |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Determination of serum amantadine by liquid chromatography-tandem mass spectrometry. | 2005 Sep |
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Glutamate receptors in neuroinflammatory demyelinating disease. | 2006 |
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[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 |
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The pharmacology of aminoadamantane nitrates. | 2006 Jul |
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Pharmacological characterization of psychosis-like behavior in the MPTP-lesioned nonhuman primate model of Parkinson's disease. | 2006 Nov |
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Behavioral effects of aminoadamantane class NMDA receptor antagonists on schedule-induced alcohol and self-administration of water in mice. | 2006 Sep |
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Identification of genes associated with cisplatin resistance in human oral squamous cell carcinoma cell line. | 2006 Sep 15 |
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Modulation of L-DOPA-induced abnormal involuntary movements by clinically tested compounds: further validation of the rat dyskinesia model. | 2007 Apr 16 |
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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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26201988
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
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NCI_THESAURUS |
C93038
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C281
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N0000175542
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C38149
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NBK547954
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m1638
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)