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
Molecular Formula | C10H17N |
Molecular Weight | 151.2487 |
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
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 |
---|---|---|
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 |
|
Neuroleptic malignant syndrome induced by haloperidol following traumatic brain injury. | 1999 Dec |
|
Amantadine-induced peripheral neuropathy. | 1999 Nov 10 |
|
The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches. | 2001 |
|
A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1. | 2001 Jun |
|
Intravenous amantadine improves levadopa-induced dyskinesias: an acute double-blind placebo-controlled study. | 2001 May |
|
[Effect of the new potential anti-Parkinson agent, hymantane, on levels of monoamines and their metabolites in rat striatum (a microdialysis study)]. | 2001 Nov-Dec |
|
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 |
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Synthesis and antioxidant activity evaluation of novel antiparkinsonian agents, aminoadamantane derivatives of nitroxyl free radical. | 2003 Aug 5 |
|
An artist's view of drug-induced hallucinosis. | 2003 Jul |
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Long term motor complications of levodopa: clinical features, mechanisms, and management strategies. | 2004 Aug |
|
Prevention of influenza in the general population. | 2004 Nov 9 |
|
Improved neurological function after Amantadine treatment in two patients with brain injury. | 2005 Apr |
|
Combined blockade of AMPA and NMDA glutamate receptors reduces levodopa-induced motor complications in animal models of PD. | 2005 Dec |
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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 |
|
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 |
|
Amantadine-induced livedo reticularis: a report of two cases. | 2006 Mar |
|
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 |
|
Pharmacological characterization of psychosis-like behavior in the MPTP-lesioned nonhuman primate model of Parkinson's disease. | 2006 Nov |
|
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 |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:36:54 UTC 2022
by
admin
on
Fri Dec 16 16:36:54 UTC 2022
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Record UNII |
BF4C9Z1J53
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C93038
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175542
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NCI_THESAURUS |
C38149
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WHO-ATC |
N04BB01
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NDF-RT |
N0000175543
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QN04BB01
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LIVERTOX |
NBK547954
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Amantadine
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BF4C9Z1J53
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AMANTADINE
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CHEMBL660
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212-201-2
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M1638
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PRIMARY | Merck Index |
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TARGET ORGANISM->INHIBITOR |
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
Amantadine is primarily excreted unchanged in the urine, and in a study of six healthy volunteers, the ratio of amantadine renal clearance to apparent plasma clearance was 0.79 ± 0.17 (mean ± SD).
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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TARGET ORGANISM->INHIBITOR |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
URINE
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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