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20-September-2008 09:55:50 - Amantadine Amantadine Systematic IUPAC name adamantan-1-amine Identifiers CAS number 768-94-5 ATC code N04BB01 PubChem 2130 DrugBank APRD00787 Chemical data Formula C10H17N Mol. mass 151.249 g/mol Pharmacokinetic data Bioavailability well absorbed Protein binding approx 67% Metabolism negligible Half life 10-14 hours, in renal impairment up to 7-10 days Excretion renal Therapeutic considerations Pregnancy cat. C Legal status Routes oral Amantadine is the organic compound known formally as 1-aminoadamantane. The molecule consists of adamantane backbone that is substituted at one of the four methyne positions with an amino group. This compound is sold under the name Symmetrel, for use both as an antiviral and an antiparkinsonian drug. Rimantadine is a closely related derivative of adamantane with similar biological properties. Contents 1 Uses 1.1 Approved 1.2 Off-label uses 2 Side effects 3 Mechanism of action 4 Misuse 5 Declining effectiveness 6 References 7 See also Uses Approved It was approved by the U.S. Food and Drug Administration in October 1966 as a prophylactic agent against Asian influenza and eventually received approval for the treatment of Influenzavirus A1234 in adults. In 1969 the drug was also discovered by accident to help reduce symptoms of Parkinson's disease and drug-induced extrapyramidal syndromes. As an antiparkinsonian 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.5 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, likely due to amantadine's dopaminergic and adrenergic activity, and to a lesser extent, its activity as an anticholinergic. CNS side effects include 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. The usefulness of amantadine as an anti-parkinsonian agent is thus limited by the need to screen patients for a history of seizures and psychiatric symptoms. In Parkinson's patients who show such symptoms, the risks of amantadine may well outweigh the benefits. Vomiting has been recorded in pigeons fed amantadine. Cases of suicidal ideation in patients treated with amantadine have been described,6 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.7 Another potential side effect is livedo reticularis, a dermatological reaction that results in skin mottling and purpurish mesh network of blood vessels. Mechanism of action The mechanism for its antiviral and antiparkinsonian effects seems to be unrelated. The mechanism of its antiparkinsonian effect is poorly understood. The drug appears to induce release of 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. In terms of the mechanism of its antiviral properties, amantadine interferes with a viral protein, M2 an ion channel, which is required for the viral particle to become uncoated once it is taken inside the cell by endocytosis. Misuse In 2005, Chinese poultry farmers were reported to have used amantadine to protect birds against avian influenza.8 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.8 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 AH3N2 and 2 25% of 8 influenza AH1N1 viruses analyzed contained point mutations resulting in a serine-to-asparagine change at amino acid 31 S31N of the M2 protein that conferred amantadine resistance.9 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.10 Among some Asian countries, A/H3N2 and A/H1N1 resistance has reached 100%.11 References ^ David A. Hounshell and John Kenly Smith, Science and Corporate Strategy: Du Pont RD, 1902-1980, 1988, Cambridge University Press, p. 469. http://books.google.com/books?id=6ld0K9VNpmIC ^ SALES OF FLU DRUG BY DU PONT UNIT A 'DISAPPOINTMENT' Last accessed May 19, 2008. October 5, 1982, The New York Times. ^ Thomas H. Maugh. Amantadine: An Alternative for Prevention of Influenza Science. April 9, 1976. 192: 130-131. DOI: 10.1126/science.386515 Article subscription required ^ T.H. Maugh. Panel urges wide use of antiviral drug Science. November 30, 1979. 206: 1058-1060. DOI: 10.1126/science.192.4235.130 Article subscription required ^ Hallowell, Edward M. and John J. Ratey, Delivered from Distraction: Getting the Most out of Life with Attention Deficit Disorder 2005, pp. 253-5. ^ Endo Pharmaceuticals. Symmetrel Amantadine Prescribing Information PDF. Retrieved on 2007-08-02. ^ Cook et al, Fatal overdose with amantadine. Can. J. Psychiatry Nov 1986; 318, pp. 757-758. ^ a b Sipress, Alan 2005-06-18. Bird Flu Drug Rendered Useless, Washington Post, pp. A01. Retrieved on 2007-08-02. ^ Bright, R A; Shay, D K; Shu, B;Cox, N J;Klimov, A I 2006-02-22. Adamantane Resistance Among Influenza A Viruses Isolated Early During the 2005-2006 Influenza Season in the United States. Journal of the American Medical Association 295 8: 891-894. doi:10.1001/jama.295.8.joc60020. ISSN 0098-7484. PMID 16456087. OCLC 194229372. BL Shelfmark 4689.000000. Retrieved on 2008-05-20. ^ CDC Recommends against the Use of Amantadine and Rimantadine for the Treatment or Prophylaxis of Influenza in the United States during the 2005-06 Influenza Season. CDC Health Alert. Centers for Disease Control and Prevention 2006-01-14. Retrieved on 2008-05-20. ^ Deyde, Varough M.; Xu, Xiyan; Bright, Rick A.; Shaw, Michael; Smith, Catherine B.; Zhang, Ye; Shu, Yuelong; Gubareva, Larisa V.; Cox, Nancy J.; Klimov, Alexander I. 2007-07-15. Surveillance of Resistance to Adamantanes among Influenza AH3N2 and AH1N1 Viruses Isolated Worldwide. Journal of Infectious Diseases 196 2: 249-257. doi:10.1086/518936. Retrieved on 2008-05-19. See also Rimantadine Tromantadine v d e Anti-parkinson drugs: dopaminergic agents N04B Dopa and derivatives Droxidopa Levodopa Melevodopa Etilevodopa Adamantane derivatives Amantadine Dopamine agonists A-412,997 Apomorphine Bromocriptine Cabergoline Dihydrexidine Dihydroergocryptine mesylate Fenoldopam Lisuride Pergolide Piribedil Pramipexole Propylnorapomorphine Quinpirole Ropinirole Rotigotine SKF 38393 SKF 82958 MAOIs B Selegiline Rasagiline COMT inhibitors Entacapone Tolcapone Other Budipine dopa decarboxylase inhibitor Carbidopa v d e Antivirals, other than for HIV primarily J05, also S01AD and D06BB Anti-herpesvirus DNA, I purine analogue guanine Aciclovir, Famciclovir, Ganciclovir, Penciclovir, Valaciclovir, Valganciclovir Vidarabine pyrimidine analogue uridine Idoxuridine, Trifluridine Brivudine Cidofovir Docosanol Fomivirsen Foscarnet Tromantadine HPV/MC DNA, I Imiquimod Podophyllotoxin Hepatitis B DNA, VII Adefovir Clevudine Interferon alfa-2b Pegylated interferon alfa-2a Entecavir Lamivudine Telbivudine Tenofovir†Hepatitis C RNA, IV Pegylated interferon alpha Ribavirin Taribavirin†Boceprevir†Picornavirus RNA, IV Pleconaril†Anti-influenza agents RNA, V Arbidol adamantane derivatives/M2 inhibitors Amantadine, Rimantadine neuraminidase inhibitors Oseltamivir, Zanamivir, Peramivir†HIV Reverse, VI See HIV pharm Other antiviral agents general Inosine, Interferon †Undergoing clinical trials, not FDA approved. v d e Influenza Influenza Research - Vaccine - Avian influenza - Treatment - Genome sequencing - Season Influenza viruses Orthomyxoviridae - Influenza A - Influenza B - Influenza C Subtypes of Influenza A virus H1N1 - H1N2 - H2N2 - H3N1 - H3N2 - H3N8 - H5N1 - H5N2 - H5N3 - H5N8 - H5N9 - H7N1 - H7N2 - H7N3 - H7N4 - H7N7 - H9N2 - H10N7 H5N1 Genetic structure - Transmission and infection - Global spread - Clinical Trials - Human mortality Antiviral drugs Arbidol - adamantane derivatives Amantadine, Rimantadine - neuraminidase inhibitors Oseltamivir, Peramivir, Zanamivir Experimental Peramivir Influenza vaccines FluMist - Fluzone Influenza pandemics Asian Flu - Hong Kong Flu - Spanish flu - Fujian flu - Pandemic Severity Index Outbreaks of Avian influenza Croatia 2005 - India 2006 - UK 2007 - West Bengal 2008 Influenza in non-human mammals Canine influenza - Equine influenza 2007 Australian outbreak - Swine flu Retrieved from http://en..org/wiki/Amantadine Categories: Antiparkinsonian agents | Amines | Anti-influenza agents | NMDA receptor antagonists | Antivirals Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Italiano Nederlands 日本語 Polski Português РуÑ?Ñ?кий ไทย This page was last modified on 30 July 2008, at 06:32
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