Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C10H17N.H2O4S |
Molecular Weight | 400.576 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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)
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 |
---|---|---|---|
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 |
---|---|---|---|---|
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 Date5.40518384E11 |
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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 Date5.40518384E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
0.8 g single, oral Overdose Dose: 0.8 g Route: oral Route: single Dose: 0.8 g Sources: Page: p.120 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: M Population Size: 1 Sources: Page: p.120 |
Disc. AE: Status epilepticus, Agitation... AEs leading to discontinuation/dose reduction: Status epilepticus Sources: Page: p.120Agitation Diaphoresis Vomiting |
3000 mg single, oral Overdose Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: Page: p.757 |
unhealthy, 23 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 23 Sex: M Population Size: 1 Sources: Page: p.757 |
Disc. AE: CNS toxicity... AEs leading to discontinuation/dose reduction: CNS toxicity (grade 5) Sources: Page: p.757 |
10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Co-administed with:: diphenhydramine, p.o(250 mg, single) Sources: Page: p.174 |
unhealthy, 47 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 47 Sex: F Population Size: 1 Sources: Page: p.174 |
Disc. AE: Ventricular tachycardia... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: Page: p.174 |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: Page: p.605 |
unhealthy, 53.3 n = 27 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 53.3 Sex: M+F Population Size: 27 Sources: Page: p.605 |
Disc. AE: Serotonin syndrome, Dry mouth... AEs leading to discontinuation/dose reduction: Serotonin syndrome (serious, 3.7%) Sources: Page: p.605Dry mouth (3.7%) |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: |
unhealthy, 63.9 n = 63 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 63.9 Sex: M+F Population Size: 63 Sources: |
DLT: Visual hallucinations... Disc. AE: Visual hallucinations, Peripheral edema... Dose limiting toxicities: Visual hallucinations (4.8%) AEs leading todiscontinuation/dose reduction: Visual hallucinations (7.9%) Sources: Peripheral edema (4.8%) Dry mouth (4.8%) |
420 mg 1 times / day multiple, oral Highest studied dose Dose: 420 mg, 1 times / day Route: oral Route: multiple Dose: 420 mg, 1 times / day Sources: Page: p.793 |
unhealthy, 66.4 n = 20 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 66.4 Sex: M+F Population Size: 20 Sources: Page: p.793 |
Disc. AE: Hallucinations, Balance disorder... AEs leading to discontinuation/dose reduction: Hallucinations (15%) Sources: Page: p.793Balance disorder (5%) Confusional state (5%) Dry mouth (5%) Subdural hematoma (5%) Constipation (5%) |
100 mg 3 times / day steady, oral Dose: 100 mg, 3 times / day Route: oral Route: steady Dose: 100 mg, 3 times / day Sources: |
unhealthy n = 36 Health Status: unhealthy Condition: Parkinson's disease Population Size: 36 Sources: |
Other AEs: Dry mouth... Other AEs: Dry mouth (below serious, 4 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Agitation | Disc. AE | 0.8 g single, oral Overdose Dose: 0.8 g Route: oral Route: single Dose: 0.8 g Sources: Page: p.120 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: M Population Size: 1 Sources: Page: p.120 |
Diaphoresis | Disc. AE | 0.8 g single, oral Overdose Dose: 0.8 g Route: oral Route: single Dose: 0.8 g Sources: Page: p.120 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: M Population Size: 1 Sources: Page: p.120 |
Status epilepticus | Disc. AE | 0.8 g single, oral Overdose Dose: 0.8 g Route: oral Route: single Dose: 0.8 g Sources: Page: p.120 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: M Population Size: 1 Sources: Page: p.120 |
Vomiting | Disc. AE | 0.8 g single, oral Overdose Dose: 0.8 g Route: oral Route: single Dose: 0.8 g Sources: Page: p.120 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: M Population Size: 1 Sources: Page: p.120 |
CNS toxicity | grade 5 Disc. AE |
3000 mg single, oral Overdose Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: Page: p.757 |
unhealthy, 23 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 23 Sex: M Population Size: 1 Sources: Page: p.757 |
Ventricular tachycardia | Disc. AE | 10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Co-administed with:: diphenhydramine, p.o(250 mg, single) Sources: Page: p.174 |
unhealthy, 47 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 47 Sex: F Population Size: 1 Sources: Page: p.174 |
Dry mouth | 3.7% Disc. AE |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: Page: p.605 |
unhealthy, 53.3 n = 27 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 53.3 Sex: M+F Population Size: 27 Sources: Page: p.605 |
Serotonin syndrome | serious, 3.7% Disc. AE |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: Page: p.605 |
unhealthy, 53.3 n = 27 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 53.3 Sex: M+F Population Size: 27 Sources: Page: p.605 |
Visual hallucinations | 4.8% DLT |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: |
unhealthy, 63.9 n = 63 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 63.9 Sex: M+F Population Size: 63 Sources: |
Dry mouth | 4.8% Disc. AE |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: |
unhealthy, 63.9 n = 63 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 63.9 Sex: M+F Population Size: 63 Sources: |
Peripheral edema | 4.8% Disc. AE |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: |
unhealthy, 63.9 n = 63 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 63.9 Sex: M+F Population Size: 63 Sources: |
Visual hallucinations | 7.9% Disc. AE |
274 mg 1 times / day multiple, oral Recommended Dose: 274 mg, 1 times / day Route: oral Route: multiple Dose: 274 mg, 1 times / day Sources: |
unhealthy, 63.9 n = 63 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 63.9 Sex: M+F Population Size: 63 Sources: |
Hallucinations | 15% Disc. AE |
420 mg 1 times / day multiple, oral Highest studied dose Dose: 420 mg, 1 times / day Route: oral Route: multiple Dose: 420 mg, 1 times / day Sources: Page: p.793 |
unhealthy, 66.4 n = 20 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 66.4 Sex: M+F Population Size: 20 Sources: Page: p.793 |
Balance disorder | 5% Disc. AE |
420 mg 1 times / day multiple, oral Highest studied dose Dose: 420 mg, 1 times / day Route: oral Route: multiple Dose: 420 mg, 1 times / day Sources: Page: p.793 |
unhealthy, 66.4 n = 20 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 66.4 Sex: M+F Population Size: 20 Sources: Page: p.793 |
Confusional state | 5% Disc. AE |
420 mg 1 times / day multiple, oral Highest studied dose Dose: 420 mg, 1 times / day Route: oral Route: multiple Dose: 420 mg, 1 times / day Sources: Page: p.793 |
unhealthy, 66.4 n = 20 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 66.4 Sex: M+F Population Size: 20 Sources: Page: p.793 |
Constipation | 5% Disc. AE |
420 mg 1 times / day multiple, oral Highest studied dose Dose: 420 mg, 1 times / day Route: oral Route: multiple Dose: 420 mg, 1 times / day Sources: Page: p.793 |
unhealthy, 66.4 n = 20 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 66.4 Sex: M+F Population Size: 20 Sources: Page: p.793 |
Dry mouth | 5% Disc. AE |
420 mg 1 times / day multiple, oral Highest studied dose Dose: 420 mg, 1 times / day Route: oral Route: multiple Dose: 420 mg, 1 times / day Sources: Page: p.793 |
unhealthy, 66.4 n = 20 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 66.4 Sex: M+F Population Size: 20 Sources: Page: p.793 |
Subdural hematoma | 5% Disc. AE |
420 mg 1 times / day multiple, oral Highest studied dose Dose: 420 mg, 1 times / day Route: oral Route: multiple Dose: 420 mg, 1 times / day Sources: Page: p.793 |
unhealthy, 66.4 n = 20 Health Status: unhealthy Condition: Levodopa-Induced Dyskinesia in Parkinson Disease Age Group: 66.4 Sex: M+F Population Size: 20 Sources: Page: p.793 |
Dry mouth | below serious, 4 patients | 100 mg 3 times / day steady, oral Dose: 100 mg, 3 times / day Route: oral Route: steady Dose: 100 mg, 3 times / day Sources: |
unhealthy n = 36 Health Status: unhealthy Condition: Parkinson's disease Population Size: 36 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
Neurotoxicity of chlorpromazine and modulation by amantadine as a function of mouse strain. | 1991 Fall |
|
Medication-induced hallucination and cerebral blood flow in Parkinson's disease. | 1999 May |
|
A novel approach to antiviral therapy for influenza. | 1999 Nov |
|
The effect of amantadine on levodopa-induced dyskinesias in Parkinson's disease: a double-blind, placebo-controlled study. | 2000 Mar-Apr |
|
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 |
|
Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease. | 2000 Sep |
|
Quetiapine for l-dopa-induced psychosis in PD. | 2000 Sep 26 |
|
The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches. | 2001 |
|
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior. | 2001 Jan |
|
Synthesis and pharmacological evaluation of potent and enantioselective sigma 1, and sigma 2 ligands. | 2001 Mar |
|
Synthesis of valproic acid amides of a melatonin derivative, a piracetam and amantadine for biological tests. | 2001 Oct |
|
Chiral separation of enantiomeric 1,2-diamines using molecular imprinting method and selectivity enhancement by addition of achiral primary amines into eluents. | 2002 Jan |
|
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds. | 2002 Oct |
|
Amantadine in Huntington's disease: open-label video-blinded study. | 2002 Sep |
|
An artist's view of drug-induced hallucinosis. | 2003 Jul |
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Mirtazapine in L-dopa-induced dyskinesias. | 2003 Jul-Aug |
|
Bitterness evaluation of medicines for pediatric use by a taste sensor. | 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 |
|
Motor-learning impairment by amantadine in healthy volunteers. | 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 |
|
Treatment of interferon non-responsive chronic hepatitis C with triple therapy with interferon, ribavirin, and amantidine can be encouraging. | 2004 Mar |
|
Amantadine for levodopa-induced choreic dyskinesia in compound heterozygotes for GCH1 mutations. | 2004 Oct |
|
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 |
|
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 |
|
Glutamate receptors in neuroinflammatory demyelinating disease. | 2006 |
|
A novel soluble mimic of the glycolipid, globotriaosyl ceramide inhibits HIV infection. | 2006 Feb 14 |
|
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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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C281
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NCI_THESAURUS |
C93038
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9921T5P019
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SUB00423MIG
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621
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124108
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DTXSID50953416
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DBSALT000830
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m1638
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C90781
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31377-23-8
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78351
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SUB78132
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100000092128
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250-604-5
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ACTIVE MOIETY
SUBSTANCE RECORD