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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/09 07:47:15」(JST)
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| Systematic (IUPAC) name | |
|---|---|
| adamantan-1-amine | |
| Clinical data | |
| Trade names | Symmetrel |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682064 |
| Pregnancy cat. |
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| Legal status |
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| Routes | oral |
| Pharmacokinetic data | |
| Bioavailability | 86-90%[1] |
| Protein binding | 67%[1] |
| Metabolism | Minimal (mostly to acetyl metabolites)[1] |
| Half-life | 10-31 hours[1] |
| Excretion | Urine[1] |
| Identifiers | |
| CAS number | 768-94-5 Y |
| ATC code | N04BB01 |
| PubChem | CID 2130 |
| DrugBank | DB00915 |
| ChemSpider | 2045 Y |
| UNII | BF4C9Z1J53 Y |
| KEGG | D07441 Y |
| ChEBI | CHEBI:2618 Y |
| ChEMBL | CHEMBL660 Y |
| Synonyms | 1-Adamantylamine |
| Chemical data | |
| Formula | C10H17N |
| Mol. mass | 151.249 g/mol |
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| Y (what is this?) (verify) | |
Amantadine (trade name Symmetrel, by Endo Pharmaceuticals) is a drug that has U.S. Food and Drug Administration approval for use both as an antiviral and an antiparkinsonian drug. It is the organic compound 1-adamantylamine or 1-aminoadamantane, meaning it consists of an adamantane backbone that has an amino group substituted at one of the four methyne positions. Rimantadine is a closely related derivative of adamantane with similar biological properties.
Apart from medical uses, this compound is useful as a building block, allowing the insertion of an adamantyl group.
According to the U.S. Centers for Disease Control and Prevention, 100% of seasonal H3N2 and 2009 pandemic flu samples tested have shown resistance to adamantanes, and amantadine is no longer recommended for treatment of influenza in the United States. Additionally, its effectiveness as an antiparkinsonian drug is undetermined, with a 2003 Cochrane Review concluding that there was insufficient evidence in support or against its efficacy and safety.[2]
Contents
- 1 History
- 2 Indications
- 2.1 Parkinson's disease
- 2.2 Influenza
- 2.3 Off-label uses
- 3 Adverse effects
- 4 Physical and chemical properties
- 4.1 Synthesis
- 5 Mechanism of anti-influenza action
- 6 Mechanism of action in Parkinsons disease
- 7 Dosage and clinical apsects
- 7.1 As an antiviral agent
- 7.2 As an agent in Parkinsons
- 8 Research in brain injury
- 9 Veterinary misuse
- 10 Carmantidine
- 11 See also
- 12 References
History
Amantadine 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 A[3][4][5][6] in adults. In 1969, the drug was also discovered by accident to help reduce symptoms of Parkinson's disease, drug-induced extrapyramidal syndromes, and akathisia.
Indications
Parkinson's disease
Amantadine is a weak antagonist of the NMDA type glutamate receptor, increases dopamine release, and blocks dopamine reuptake. This makes it a weak therapy for Parkinson's disease. Although, 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).
A 2003 Cochrane review of the scientific literature concluded that there was inadequate evidence to support the use of amantadine for Parkinson's disease.[2]
Influenza
Amantadine is no longer recommended for treatment of influenza A infection.
For the 2008/2009 flu season, the United States' Centers for Disease Control and Prevention (CDC) found that 100% of seasonal H3N2 and 2009 pandemic flu samples tested have shown resistance to adamantanes.[7] The CDC issued an alert to doctors to prescribe the neuraminidase inhibitors oseltamivir and zanamivir instead of amantadine and rimantadine for treatment of current circulating flu.[8][9]
Off-label uses
Amantadine is frequently used to treat the chronic fatigue often experienced by patients with multiple sclerosis.[10] Additionally, there have been anecdotal reports[11] and a small number of pilot studies[12][13] that show low-dose amantadine as a potential treatment for ADHD. Limited data has shown that amantadine may help to relieve SSRI-induced sexual dysfunction.[14][15][16]
Some open-label uncontrolled studies have found it to possess value as an adjunct to antidepressant therapy.[17]
Adverse effects
Amantadine has been associated with several central nervous system (CNS) 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 drug is somewhat limited by the need to screen patients for a history of seizures and psychiatric symptoms.
Rare cases of severe skin rashes, such as Stevens-Johnson syndrome,[18] and of suicidal ideation have also been reported in patients treated with amantadine.[19][20]
Livedo reticularis is a possible side effect of amantadine use for Parkinson's disease.[21]
Physical and chemical properties
Synthesis
Amantadine may be prepared by reacting adamantane with bromine or nitric acid to give the bromide or nitroester at position one. Reaction of either compound with acetonitrile affords the acetamide, which is hydrolyzed to give 1-adamantylamine:[22][23][24]
Mechanism of anti-influenza action
| This section relies on references to primary sources. Please add references to secondary or tertiary sources. (June 2014) |
The mechanisms for amantadine's antiviral and antiparkinsonian effects are unrelated. The mechanism of amantadine's antiviral activity involves interference with the viral protein, M2, a proton channel.[25][26] After entry of the virus into cells via endocytosis, it is localized in acidic vacuoles; the M2 channel functions in transporting protons with the gradient from the vacuolar space into to interior of the virion. Acidification of the interior results in disassociation of ribonucleoproteins, and the onset of viral replication. Amantadine and rimantadine function in a mechanistically identical fashion in entering the barrel of the tetrameric M2 channel, and blocking pore function (i.e., proton translocation). Resistance to the drug class is a consequence of mutations to the pore-lining residues of the channel, leading to the inability of the sterically bulky adamantane ring that both share in entering in their usual way, into the channel.[citation needed]
Influenza B strains possess a structurally distinct M2 channels with channel-facing side chains that fully obstruct the channel vis-a-vis binding of adamantine-calss channel inhibitors, while still allowing proton flow and channel function to occur; this constriction in the channels is responsible for the ineffectiveness of this drug and rimantadine towards all circulating Influenza B strains.
Mechanism of action in Parkinsons disease
| This section relies on references to primary sources. Please add references to secondary or tertiary sources. (June 2014) |
Amantadine appears to act through several pharmacological mechanisms, but no dominant mechanism of action has been identified. It is a dopaminergic, noradrenergic and serotonergic substance, blocks monoamine oxidase A and NMDA receptors, and seems to raise beta-endorphin/beta-lipotropin levels.[citation needed] Moreover, the mechanism of its antiparkinsonian effect is poorly understood.[citation needed] The drug has many effects in the brain, including release of dopamine and norepinephrine from nerve endings. It appears to be a weak NMDA receptor antagonist[27][28] as well as an anticholinergic, specifically a nicotinic alpha-7 antagonist like the similar pharmaceutical memantine.
Dosage and clinical apsects
| This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (June 2014) |
As an antiviral agent
Many influenza A strains (and virtually all H1N1 "swine flu" strains) are resistant to amantadine, so a failure at this usual starting dose of 100 mg once daily is likely to fail.[citation needed]
As an agent in Parkinsons
For its anti-Parkinsonian effects, a starting dose of 300 mg once daily is normal, but can be increased to a limit of about 400 mg.[citation needed]
Research in brain injury
In a 2012 study, 184 patients with severe traumatic brain injury were treated with amantadine or placebo for four weeks. In this study, the drug accelerated functional brain recovery during treatment. However, the placebo group had improved just as much as the amantadine group at six weeks — two weeks after the drug administration ended.[29]
Veterinary misuse
In 2005, Chinese poultry farmers were reported to have used amantadine to protect birds against avian influenza.[30] 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.[30] Avian flu (H5N1) strains in China and southeast Asia are now resistant to amantadine, although strains circulating elsewhere still seem to be sensitive. If amantadine-resistant strains of the virus spread, the drugs of choice in an avian flu outbreak will probably be restricted to the scarcer and costlier oseltamivir and zanamivir, which work by a different mechanism and are less likely to trigger resistance.
Carmantidine
The high lipophilicity of adamantyl moieties suggests that drugs containing them might pass into tissues of high lipid content or cross the bloodbrain barrier. Indeed carmantadine is active against the spasms associated with Parkinson's disease.
Carmantidine synthesis: Elijah H Gold, Schering Corp, U.S. Patent 3,917,840 Chem.Abstr. , 84: 59221k (1976).
Amantadine reacts with methyl 2,4-dibromobutyrate to give ester which can be hydrolyzed with aqueous barium hydroxide to complete the synthesis of carmantidine.
See also
-
Somantadine U.S. Patent 4,100,170
- Memantine
- Rimantadine
- Tromantadine
- Somantadine
- Bromantane
- Carmantidine
References
- ^ a b c d e "SYMMETREL® (amantadine hydrochloride)" (PDF). TGA eBusiness Services. NOVARTIS Pharmaceuticals Australia Pty Limited. 29 June 2011. Retrieved 24 February 2014.
- ^ a b Crosby, Niall J; Deane, Katherine; Clarke, Carl E (2003). "Amantadine in Parkinson's disease". In Clarke, Carl E. Cochrane Database of Systematic Reviews. doi:10.1002/14651858.CD003468.
- ^ David A. Hounshell and John Kenly Smith, "Science and Corporate Strategy: Du Pont R&D, 1902-1980", 1988, Cambridge University Press, p. 469.
- ^ "Sales of flu drug by du Pont unit a 'disappointment'" (Last accessed May 19, 2008.) October 5, 1982, The New York Times.
- ^ Maugh, T. (1979). "Panel urges wide use of antiviral drug". Science 206 (4422): 1058–60. doi:10.1126/science.386515. PMID 386515.
- ^ Maugh, T. H. (1976). "Amantadine: an Alternative for Prevention of Influenza". Science 192 (4235): 130–1. doi:10.1126/science.192.4235.130. PMID 17792438.
- ^ CDC weekly influenza report - week 35, cdc.gov
- ^ "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. Archived from the original on 3 May 2008. Retrieved 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). "Surveillance of Resistance to Adamantanes among Influenza A(H3N2) and A(H1N1) Viruses Isolated Worldwide". Journal of Infectious Diseases 196 (2): 249–257. doi:10.1086/518936. PMID 17570112.
- ^ Cohen, RA; Fisher, M (1989). "Amantadine treatment of fatigue associated with multiple sclerosis". Archives of neurology 46 (6): 676–80. doi:10.1001/archneur.1989.00520420096030. PMID 2730380.
- ^ Hallowell, Edward M. and John J. Ratey, Delivered from Distraction: Getting the Most out of Life with Attention Deficit Disorder (2005), pp. 253-5 ISBN 0-345-44230-X
- ^ Mohammadi, MR; Kazemi MR; Zia E; Rezazadeh SA; Tabrizi M; Akhondzadeh S (November 2010). "Amantadine versus methylphenidate in children and adolescents with attention deficit/hyperactivity disorder: a randomized, double-blind trial". Human Psychopharmacology: Clinical and Experimental 25: 560–6. doi:10.1002/hup.1154. PMID 21312290.
|accessdate=requires|url=(help) - ^ Donfrancesco, Renato; Calderoni, D; Vitiello, B (2007). "Open-Label Amantadine in Children with Attention-Deficit/Hyperactivity Disorder". Journal of Child and Adolescent Psychopharmacology 17 (5): 657–663. doi:10.1089/cap.2006.0128. PMID 17979585.
|accessdate=requires|url=(help) - ^ Shrivastava RK, Shrivastava S, Overweg N, Schmitt M (1995). "Amantadine in the treatment of sexual dysfunction associated with selective serotonin reuptake inhibitors". Journal of clinical psychopharmacology 15 (1): 83–4. doi:10.1097/00004714-199502000-00014. PMID 7714234.
- ^ Balogh S, Hendricks SE, Kang J (1992). "Treatment of fluoxetine-induced anorgasmia with amantadine". The Journal of clinical psychiatry 53 (6): 212–3. PMID 1607353.
- ^ Keller Ashton A, Hamer R, Rosen RC (1997). "Serotonin reuptake inhibitor-induced sexual dysfunction and its treatment: a large-scale retrospective study of 596 psychiatric outpatients". Journal of sex & marital therapy 23 (3): 165–75. doi:10.1080/00926239708403922. PMID 9292832.
- ^ Stryjer, R; Strous RD; Shaked G; Bar F; Feldman B; Kotler M; Polak L; Rosenzcwaig S; Weizman A (2003). "Amantadine as augmentation therapy in the management of treatment-resistant depression.". International Journal of Psychopharmacology 18 (2): 93–96. doi:10.1097/00004850-200303000-00005. PMID 12598820.
- ^ K C Singhal & S Z Rahman, Stevens Johnson Syndrome induced by Amantadine, Rational Drug Bulletin, 2002, Vol. 12, No. 1: 6
- ^ Endo Pharmaceuticals (May 2003). Symmetrel (Amantadine) Prescribing Information (PDF). Retrieved 2007-08-02.
- ^ Cook, PE; Dermer, SW; McGurk, T (1986). "Fatal overdose with amantadine". Canadian Journal of Psychiatry 31 (8): 757–8. PMID 3791133.
- ^ Vollum DI, Parkes JD, Doyle D (June 1971). "Livedo reticularis during amantadine treatment". Br Med J 2 (5762): 627–8. doi:10.1136/bmj.2.5762.627. PMC 1796527. PMID 5580722.
- ^ Moiseev, I. K.; Doroshenko, R. I.; Ivanova, V. I. (1976). "Synthesis of amantadine via the nitrate of 1-adamantanol". Pharmaceutical Chemistry Journal 10 (4): 450. doi:10.1007/BF00757832. edit
- ^ H. Stetter, J. Mayer, M. Schwarz, K. Wulf (1960). "Über Verbindungen mit Urotropin-Struktur, XVI. Beiträge zur Chemie der Adamantyl-(1)-Derivate". Chem. Ber. 93: 226. doi:10.1002/cber.19600930133.
- ^ J.C. Watts, P. Marvin, U.S. Patent 3,310,469 (1967).
- ^ Wang C, Takeuchi K, Pinto LH, Lamb RA (1993). "Ion channel activity of influenza A virus M2 protein: characterization of the amantadine block". Journal of Virology 67 (9): 5585–94. PMC 237962. PMID 7688826.
- ^ Jing X, Ma C, Ohigashi Y, et al. (2008). "Functional studies indicate amantadine binds to the pore of the influenza A virus M2 proton-selective ion channel". Proc. Natl. Acad. Sci. U.S.A. 105 (31): 10967–72. doi:10.1073/pnas.0804958105. PMC 2492755. PMID 18669647.
- ^ Kornhuber J, Bormann J, Hübers M, Rusche K, Riederer P (1991) "Effects of the 1-amino-adamantanes at the MK-801-binding site of the NMDA-receptor-gated ion channel: a human postmortem brain study." Eur.J.Pharmacol.Mol.Pharmacol.Sect. 206:297-300.
- ^ Blanpied TA, Clarke RJ, Johnson JW (2005). "Amantadine inhibits NMDA receptors by accelerating channel closure during channel block". Journal of Neuroscience 25 (13): 3312–22. doi:10.1523/JNEUROSCI.4262-04.2005. PMID 15800186.
- ^ Giacino, J. T.; Whyte, J.; Bagiella, E.; Kalmar, K.; Childs, N.; Khademi, A.; Eifert, B.; Long, D.; Katz, D. I.; Cho, S.; Yablon, S. A.; Luther, M.; Hammond, F. M.; Nordenbo, A.; Novak, P.; Mercer, W.; Maurer-Karattup, P.; Sherer, M. (2012). "Placebo-Controlled Trial of Amantadine for Severe Traumatic Brain Injury". New England Journal of Medicine 366 (9): 819–826. doi:10.1056/NEJMoa1102609. PMID 22375973. edit
- ^ a b Sipress, Alan (2005-06-18). "Bird Flu Drug Rendered Useless". Washington Post. pp. A01. Retrieved 2007-08-02.
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UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
- 1. パーキンソン病の薬理学的治療 pharmacologic treatment of parkinson disease
- 2. インフルエンザに対する抗ウイルス剤の薬理学 pharmacology of antiviral drugs for influenza
- 3. 成人における単極性大うつ病：刺激薬および stimulant-like drugsによる抗うつ薬の増強 unipolar major depression in adults augmentation of antidepressants with stimulants and stimulant like drugs
- 4. ハンチントン病：管理 huntington disease management
- 5. パーキンソン病における症状の変動およびジスキネジア motor fluctuations and dyskinesia in parkinson disease
English Journal
- Treatment of Apathy in Huntington's Disease and Other Movement Disorders.
- Krishnamoorthy A, Craufurd D.SourceMaelor Hospital, Wrexham, LL13 7TD, UK, ashokpriya@gmail.com.
- Current treatment options in neurology.Curr Treat Options Neurol.2011 Oct;13(5):508-19.
- OPINION STATEMENT: Apathy is one of the most prevalent neurobehavioral symptoms in Huntington's disease (HD), occurring in approximately 70% of the symptomatic HD population. Apathy scores in patients with HD are highly correlated with duration of illness, suggesting that apathy is an inevitable con
- PMID 21800056
- An improved model to investigate the efficacy of antidyskinetic agents in hemiparkinsonian rats.
- Spinnewyn B, Charnet C, Cornet S, Roubert V, Chabrier PE, Auguet M.SourceIpsen Innovation, 5 avenue du Canada, 91940 Les Ulis, France.
- Fundamental & clinical pharmacology.Fundam Clin Pharmacol.2011 Oct;25(5):608-18. doi: 10.1111/j.1472-8206.2010.00883.x. Epub 2010 Nov 16.
- A number of experimental models of L-DOPA-induced dyskinesia have been proposed, but these models result in a low to medium rate of dyskinetic animals with mild to severe symptoms. The objective of this study was to combine a model of 6-OHDA-induced parkinsonism and of L-DOPA-induced dyskinesia in r
- PMID 21077938
Japanese Journal
- インフルエンザ流行期での淀川水系における抗インフルエンザ薬タミフル及びその活性代謝物、リレンザ、アマンタジンの存在実態 (京都大学環境衛生工学研究会 第33回シンポジウム講演論文集)
- 東 剛志,中田 典秀,山下 尚之 [他]
- 環境衛生工学研究 25(3), 112-115, 2011-07
- NAID 40018935087
- 症例 Amantadineが奏効した遷延性重症低血糖昏睡の1例
- 三嶋 崇靖,樋口 正晃,津川 潤 [他]
- 内科 107(4), 739-742, 2011-04
- NAID 40018771210
Related Links
- アマンタジン (Amantadine) は示性式C10H15NH2、分子量151のアミン。別名1-アミノ アダマンタン、トリシクロ[3.3.1.13,7]デカン-1-アミン 。アダマンタンにアミノ基がついた 構造をしている。実際の製剤名は塩酸アマンタジン。CAS登録番号は768-94-5、塩酸塩 ...
- Amantadine (trade name Symmetrel, by Endo Pharmaceuticals) is a drug that has US Food and Drug Administration approval for use both as an antiviral and an antiparkinsonian drug. It is the organic compound 1-adamantylamine or ...
Related Pictures
★リンクテーブル★
| リンク元 | 「インフルエンザ」「アマンタジン」「パーキンソン病治療薬」 |
「インフルエンザ」
- 英
- influenza, Flu, flu
- 同
- 流行性感冒、epidemic catarrh
- 関
- インフルエンザウイルス。A型インフルエンザ、B型インフルエンザ
概念
病原体
- オルソミクソウイルス科のA型インフルエンザウイルス属、B型インフルエンザウイルス属、あるいはC型インフルエンザウイルス属に所属するウイルスによる感染症 (→インフルエンザウイルス)
潜伏期間
- 1-5日
感染経路
疫学
- 冬期に流行
症状
合併症
- 細菌性肺炎
- 気道粘膜の抵抗性低下、貪食細胞の機能低下による。
- 起炎菌：黄色ブドウ球菌、肺炎連鎖菌、インフルエンザ桿菌。
- ライ症侯群
- 中枢神経合併症で小児に見られる。インフルエンザ及び水痘感染に際してみられる重篤な合併症。新形態射精疾患(急性非炎症性脳炎、脂肪肝から肝機能障害も起こす)。解熱剤として使われたアスピリンとの因果関係がある、らしい。このため、インフルエンザの解熱、とりわけ小児についてはアセトアミノフェンを使うこととなっている。
- 中枢神経症状
- A型インフルエンザウイルスによる上気道炎回復後2-3週間に発症。脳炎タイプは一過性で予後はよい。脳症タイプは予後が悪い。
経過
- 全身症状(発熱、頭痛、悪寒、筋肉痛)→局所症状(咳、咽頭痛)→鼻汁、結膜充血、流涙→局所症状の始まりから2-3日で回復
- 感染力は発症直前から発症後3日までが最も強い。発症から7日間はウイルスを排出する。
治療
治療薬
- オセルタミビル oseltamivir
- ザナミビル zanamivir
- アマンタジン amantadine
- ペラミビル peramivir
- バロキサビル baloxavir
検査
- ウイルス分離：MDCK細胞に接種しCPEの観察。発育鶏卵を利用した羊膜amniotic cavity内接種。尿膜allantoic cavity内培養
- ウイルス粒子検出：PCR
- 血清診断：ペア血清を用いて、赤血球凝集抑制試験、補体結合反応、中和試験で診断
予防
- 香港A型、ソ連A型、およびB型のウイルスが含まれる
- 精製ウイルスからエーテル処理により脂質を除去したもの
- →表面抗原に対する抗体は誘導されない→感染時に症状を軽減する効果
法令
- 感染症法：五類感染症<定点>インフルエンザ定点(週)
- 学校保健安全法施行規則：第二種。解熱した後2日を経過するまで。
「アマンタジン」
- 英
- amantadine
- 化
- 塩酸アマンタジン amantadine hydrochloride、アマンタジン塩酸塩
- 商
- アテネジン、アマゾロン、シンメトレル Symmetrel、トーファルミン、ボイダン、ロティファミン
- パーキンソン病治療薬
- ドパミン放出促進
- 抗ウイルス薬
- インフルエンザ治療薬
歴史
- 最初、A型インフルエンザに対する抗ウイルス薬として使われていたが、パーキンソン病患者がアマンタジンを服用したところパーキンソン病の症状が改善されたことから、パーキンソン病への薬効が見いだされた。
薬理作用
パーキンソン病治療薬
- シナプス間隙におけるドーパミンの増量作用
- ドーパミンの合成促進
- ドーパミンの再取り込み抑制
- ドーパミンの遊離促進