Amantadine
 | |
| Clinical data | |
|---|---|
| Pregnancy category |
|
| Routes of administration | oral |
| ATC code | |
| Pharmacokinetic data | |
| Bioavailability | well absorbed |
| Protein binding | approx 67% |
| Metabolism | negligible |
| Elimination half-life | 10-14 hours, in renal impairment up to 7-10 days |
| Excretion | renal |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C10H17N |
| Molar mass | 151.249 g/mol |
|
WikiDoc Resources for Amantadine |
|
Articles |
|---|
|
Most recent articles on Amantadine |
|
Media |
|
Evidence Based Medicine |
|
Clinical Trials |
|
Ongoing Trials on Amantadine at Clinical Trials.gov Clinical Trials on Amantadine at Google
|
|
Guidelines / Policies / Govt |
|
US National Guidelines Clearinghouse on Amantadine
|
|
Books |
|
News |
|
Commentary |
|
Definitions |
|
Patient Resources / Community |
|
Patient resources on Amantadine Discussion groups on Amantadine Patient Handouts on Amantadine Directions to Hospitals Treating Amantadine Risk calculators and risk factors for Amantadine
|
|
Healthcare Provider Resources |
|
Causes & Risk Factors for Amantadine |
|
Continuing Medical Education (CME) |
|
International |
|
|
|
Business |
|
Experimental / Informatics |
Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [1] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.
For patient information, please click here
Overview
Amantadine (1-aminoadamantane, sold as Symmetrel) is an antiviral drug used both as an antiviral and an antiparkinsonic.
Uses
Approved
It was approved by the Food and Drug Administration in 1976 for the treatment of Influenzavirus A in adults. In 1969 the drug was also discovered by accident to help reduce symptoms of Parkinson's disease and drug-induced extrapyramidal syndromes. It is a derivative of adamantane, like rimantadine, a similar drug.
As an antiparkinsonic it can be used as monotherapy; or together with L-DOPA to treat L-DOPA-related motor fluctuations (i.e., shortening of L-DOPA duration of clinical effect, probably related to progressive neuronal loss) and L-DOPA-related dyskinesias (choreiform movements associated with long-term L-DOPA use, probably related to chronic pulsatile stimulation of dopamine receptors).
Off-label uses
There have been anecdotal reports, based on research by Dr. William Singer of Harvard University, that low-dose amantadine has been successfully used to treat ADHD.[1] Amantadine has been shown to relieve SSRI-induced anorgasmia in some people, though not in all people.
Side Effects
Amantadine has been associated with several central nervous system side effects, including nervousness, anxiety, agitation, insomnia, difficulty in concentrating, and exacerbations of pre-existing seizure disorders and psychiatric symptoms in patients with schizophrenia or Parkinson's disease. These side effects are likely due to amantadine's dopaminergic and adrenergic activity, and to a lesser extent, its activity as an anticholinergic.
Cases of suicidal ideation in patients treated with amantadine have been described,[2] although this psychiatric adverse event is relatively rare. Nonetheless, clinical surveillance of suicidal ideation in patients on amantadine is warranted at the clinician's discretion, as amantadine has been implicated as the major fatal (biologically toxic) factor in completed patient suicides.[3]
Another potential side effect is livedo reticularis, a dermatological reaction that results in skin mottling and purpurish mesh network of blood vessels.
Mechanism of its effects
The mechanism of its antiparkinsonic effect is not fully understood, but it appears to be releasing dopamine from the nerve endings of the brain cells, together with stimulation of norepinephrine response. Furthermore, it appears to be a weak NMDA receptor antagonist and an anticholinergic.
The antiviral mechanism seems to be unrelated. The drug interferes with a viral protein, M2 (an ion channel), which is needed for the viral particle to become "uncoated" once it is taken inside the cell by endocytosis.
Misuse
Recently, amantadine is reported to have been used in China poultry farming in an effort to protect the birds against avian influenza.[4] In western countries and according to international livestock regulations, amantadine is approved only for use in humans. Chickens in China have received an estimated 2.6 billion doses of amantadine.[4] Avian flu (H5N1) strains in China and southeast Asia are resistant to amantadine, but strains circulating elsewhere seem to be sensitive. If amantadine resistant strains of the virus spread, the drug of choice in an avian flu outbreak will likely be restricted to one of the scarcer and costlier oseltamivir or zanamivir, which work by a different mechanism and are less likely to trigger resistance.
Declining effectiveness
Early in the 2005/2006 flu season, the United States' Center for Disease Control [CDC] found rates of amantadine resistance to be much higher than in previous seasons. Looking at samples from 26 states yielded the following findings:
A total of 193 (92.3%) of 209 influenza A(H3N2) and 2 (25%) of 8 influenza A(H1N1) viruses analyzed contained point mutations resulting in a serine-to-asparagine change at amino acid 31 (S31N) of the M2 protein that conferred adamantane resistance. [2]
A resistance rate of 92% for the major flu strain was called "alarmingly high". The CDC issued an alert to doctors not to prescribe amantadine any more for the season.[3] Among some Asian countries, A/H3N2 and A/H1N1 resistance has reached 100%.[5]
References
- ↑ Hallowell, Edward M. and John J. Ratey, Delivered from Distraction: Getting the Most out of Life with Attention Deficit Disorder (2005), pp. 253-5.
- ↑ Template:Cite paper
- ↑ Cook et al, "Fatal overdose with amantadine". Can. J. Psychiatry (Nov 1986); 31(8), pp. 757-758.
- ↑ 4.0 4.1 Sipress, Alan (2005-06-18). "Bird Flu Drug Rendered Useless". Washington Post. pp. A01. Retrieved 2007-08-02.
- ↑ Deyde, Varough M. (2007-07-15). "Surveillance of Resistance to Adamantanes among Influenza A(H3N2) and A(H1N1) Viruses Isolated Worldwide". Journal of Infectious Diseases. 196 (2): 249–257. Retrieved 2007-08-02. Unknown parameter
|coauthors=ignored (help)
See also
|
Influenza Microchapters |
|
Diagnosis |
|---|
|
Treatment |
|
Case Studies |
|
Amantadine On the Web |
|
American Roentgen Ray Society Images of Amantadine |
- Pages with script errors
- Pages with citations using unsupported parameters
- E number from Wikidata
- ECHA InfoCard ID from Wikidata
- Chemical articles with unknown parameter in Infobox drug
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Drugs with no legal status
- Articles containing unverified chemical infoboxes
- Antiparkinsonian agents
- Amines
- Anti-influenza agents