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
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)
| 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 |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 00:42:12 UTC 2019
by
admin
on
Tue Oct 22 00:42:12 UTC 2019
|
| Record UNII |
9921T5P019
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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NCI_THESAURUS |
C281
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NCI_THESAURUS |
C93038
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SUB00423MIG
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M1638
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