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a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/10/21 19:06:08」(JST)

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Amantadine (trade name Symmetrel, by Endo Pharmaceuticals) is a medication that has U.S. Food and Drug Administration approval for use both as an antiviral and an antiparkinsonian medication. 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 in organic synthesis, allowing the insertion of an adamantyl group.

According to the U.S. Centers for Disease Control and Prevention (CDC) 100% of seasonal H3N2 and 2009 pandemic flu samples tested showed 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 of or against its efficacy and safety.^[2]

Medical uses

Parkinson's disease

Amantadine is used to treat Parkinson's disease, as well as parkinsonism syndromes.^[3] A 2003 Cochrane review concluded evidence was inadequate to support the use of amantadine for Parkinson's disease.^[2]

An extended release formulation is used to treat dyskinesia, a side effect of levodopa which is taken by people who have Parkinsons.^[4]

Influenza

Amantadine is no longer recommended for treatment of influenza A infection. For the 2008/2009 flu season, the CDC found that 100% of seasonal H3N2 and 2009 pandemic flu samples tested have shown resistance to adamantanes.^[5] The CDC issued an alert to doctors to prescribe the neuraminidase inhibitors oseltamivir and zanamivir instead of amantadine and rimantadine for treatment of flu.^[6]^[7] A 2014 Cochrane review did not find benefit for the prevention or treatment of influenza A.^[8]

Fatigue in multiple sclerosis

Amantadine also seems to have moderate effects on multiple sclerosis (MS) related fatigue.^[9]

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,^[10] and of suicidal ideation have also been reported in patients treated with amantadine.^[11]^[12]

Livedo reticularis is a possible side effect of amantadine use for Parkinson's disease.^[13]

Mechanism of action

Influenza

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.^[14]^[15] 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 the interior of the virion. Acidification of the interior results in disassociation of ribonucleoproteins, and the initiation of viral replication. Amantadine and rimantadine function in a mechanistically-identical fashion, 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, preventing both amantadine and rimantadine from inhibiting the channel in their usual way.^{[citation needed]}

Influenza B strains possess a structurally distinct M₂ channel with channel-facing side chains that fully obstruct the channel vis-à-vis binding of adamantine-class 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.^{[citation needed]}

Parkinson's disease

Amantadine is a weak antagonist of the NMDA-type glutamate receptor, increases dopamine release, and blocks dopamine reuptake.^[16] Amantadine probably does not inhibit MAO enzyme.^[17] Moreover, the mechanism of its antiparkinsonian effect is poorly understood^[18]. 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^[19]^[20] as well as an anticholinergic, specifically a nicotinic alpha-7 antagonist like the similar pharmaceutical memantine.

In 2004, it was discovered that amantadine and memantine bind to and act as agonists of the σ₁ receptor (K_i = 7.44 µM and 2.60 µM, respectively), and that activation of the σ₁ receptor is involved in the dopaminergic effects of amantadine at therapeutically relevant concentrations.^[21] These findings may also extend to the other adamantanes such as adapromine, rimantadine, and bromantane, and could explain the psychostimulant-like effects of this family of compounds.^[21]

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^[22]^[23]^[24]^[25] in adults. In 1969, the drug was also discovered by accident upon trying to help reduce symptoms of Parkinson's disease, drug-induced extrapyramidal syndromes, and akathisia.

In 2017, the U.S. Food and Drug Administration approved the use of amantadine in an extended release formulation developed by Adamas Pharma for the treatment of dyskinesia, an adverse effect of levodopa, that people with Parkinson's experience.^[26]

Veterinary misuse

In 2005, Chinese poultry farmers were reported to have used amantadine to protect birds against avian influenza.^[27] 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.^[27] 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 neuraminidase inhibitors oseltamivir and zanamivir which block the action of viral neuraminidase enzyme on the surface of influenza virus particles.^[28] However, there is an increasing incidence of oseltamivir resistance in circulating influenza strains (e.g.: H1N1), highlighting the serious need for the development of new anti-influenza therapies.^[29]

On September 23, 2015, the US Food and Drug Administration announced the recall of Dingo Chip Twists "Chicken in the Middle" dog treats because the product has the potential to be contaminated with amantadine.^[30]

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). Clarke, Carl E, ed. "Amantadine in Parkinson's disease". Cochrane Database of Systematic Reviews. doi:10.1002/14651858.CD003468.
^ "Amantadine – FDA prescribing information,". Drugs.com. Retrieved 2017-08-28.
^ "Amantadine extended release capsules" (PDF). FDA. August 2017. For label updates, see FDA index page for NDA 208944
^ 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 2008-05-03. 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.
^ Alves Galvão, MG; Rocha Crispino Santos, MA; Alves da Cunha, AJ (21 November 2014). "Amantadine and rimantadine for influenza A in children and the elderly". The Cochrane Database of Systematic Reviews. 11: CD002745. doi:10.1002/14651858.CD002745.pub4. PMID 25415374.
^ Braley, TJ; Chervin, RD (Aug 2010). "Fatigue in multiple sclerosis: mechanisms, evaluation, and treatment". Sleep. 33 (8): 1061–7. PMC 2910465. PMID 20815187.
^ Singhal, KC; Rahman, SZ (2002). "Stevens Johnson Syndrome Induced by Amantadine". Rational Drug Bulletin. 12 (1): 6.
^ "Symmetrel (Amantadine) Prescribing Information" (PDF). Endo Pharmaceuticals. May 2003. 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.
^ 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.
^ Jasek, W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. p. 3962. ISBN 978-3-85200-181-4.
^ Strömberg, U.; Svensson, T. H. (November 1971). "Further Studies on the Mode of Action of Amantadine". wiley.com. Acta Pharmacologica et Toxicologica, Nordic Pharmacological Society. 30 (3–4): 161–171. doi:10.1111/j.1600-0773.1971.tb00646.x.
^ https://www.ncbi.nlm.nih.gov/mesh/68000547
^ 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. doi:10.1016/0922-4106(91)90113-v.
^ 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.
^ ^a ^b Peeters, Magali; Romieu, Pascal; Maurice, Tangui; Su, Tsung-Ping; Maloteaux, Jean-Marie; Hermans, Emmanuel (2004). "Involvement of the sigma1 receptor in the modulation of dopaminergic transmission by amantadine". European Journal of Neuroscience. 19 (8): 2212–2220. doi:10.1111/j.0953-816X.2004.03297.x. ISSN 0953-816X. PMID 15090047.
^ Hounshell, David A.; Kenly Smith, John (1988). Science and Corporate Strategy: Du Pont R&D, 1902–1980. Cambridge University Press. p. 469.
^ "Sales of flu drug by du Pont unit a 'disappointment'". The New York Times. Wilmington, Delaware. October 5, 1982. Retrieved May 19, 2008.
^ 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.
^ Bastings, Eric. "NDA 208944 Approval Letter" (PDF).
^ ^a ^b Sipress, Alan (2005-06-18). "Bird Flu Drug Rendered Useless". Washington Post. pp. A01. Retrieved 2007-08-02.
^ Kumar (April 2018). "The emerging influenza virus threat: status and new prospects for its therapy and control". Archives of Virology (4): 831–844. doi:10.1007/s00705-018-3708-y.
^ Aoki (2007). "Influenza virus susceptibility and resistance to oseltamivir". PMID 17944268.
^ "Enforcement Report – Week of September 23, 2015". FDA.gov. US Food and Drug Administration, US Department of Health & Human Services.

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English Journal

Role of calcium, glutamate and NMDA in major depression and therapeutic application.

Deutschenbaur L1, Beck J1, Kiyhankhadiv A1, Mühlhauser M1, Borgwardt S1, Walter M1, Hasler G1, Sollberger D1, Lang UE2.
Progress in neuro-psychopharmacology & biological psychiatry.Prog Neuropsychopharmacol Biol Psychiatry.2016 Jan 4;64:325-33. doi: 10.1016/j.pnpbp.2015.02.015. Epub 2015 Mar 4.
Major depression is a common, recurrent mental illness that affects millions of people worldwide. Recently, a unique fast neuroprotective and antidepressant treatment effect has been observed by ketamine, which acts via the glutamatergic system. Hence, a steady accumulation of evidence supporting a
PMID 25747801

Interpreting thermodynamic profiles of aminoadamantane compounds inhibiting the M2 proton channel of influenza A by free energy calculations.

Homeyer N, Ioannidis H, Kolarov F, Gauglitz G, Zikos C, Kolocouris A, Gohlke H.
Journal of chemical information and modeling.J Chem Inf Model.2015 Dec 21. [Epub ahead of print]
The development of novel anti-influenza drugs is of great importance because of the capability of influenza viruses to occasionally cross inter-species barriers and to rapidly mutate. One class of anti-influenza agents, aminoadamantanes, including the drugs amantadine and rimantadine now widely aban
PMID 26690735

Catatonia in Neurologic and Psychiatric Patients at a Tertiary Neurological Center.

Espinola-Nadurille M1, Ramirez-Bermudez J1, Fricchione GL1, Ojeda-Lopez MC1, Perez-González AF1, Aguilar-Venegas LC1.
The Journal of neuropsychiatry and clinical neurosciences.J Neuropsychiatry Clin Neurosci.2015 Dec 16:appineuropsych15090218. [Epub ahead of print]
This study describes the prevalence, phenomenology, treatment, and outcome of neurological patients and psychiatric patients with catatonia at a tertiary neurological center. Clinical variables included nosological diagnoses and complications. Admission length and days with catatonia were used as ou
PMID 26670787

Japanese Journal

薬物療法主な治療薬の種類と特徴ドパミン放出促進薬--概要,薬理作用,用法・用量,有用性,副作用とその対策 (パーキンソン病--基礎・臨床研究のアップデート) -- (治療)

高橋一司
日本臨床 67(-) (958), 379-385, 2009-06
NAID 40016708987

Amantadine hydrochloride が著効した難治性小児欠神てんかんの1女児例

松重武志,松藤博紀,市山高志,古川漸
脳と発達 = OFFICIAL JOURNAL OF THE JAPANESE SOCIETY OF CHILD NEUROLOGY 39(4), 309-310, 2007-07-01
NAID 10019732285

橋外髄鞘崩壊症により生じた認知機能障害に塩酸アマンタジンが奏効した1症例

安藤英祐,市村篤,猪股誠司 [他]
精神医学 48(7), 765-768, 2006-07
NAID 40007311685

Related Pictures

★リンクテーブル★

リンク元	「アマンタジン」
関連記事	「hydrochloride」

「アマンタジン」

Amantadine
Clinical data
Trade names	Symmetrel
Synonyms	1-Adamantylamine
AHFS/Drugs.com	Monograph
MedlinePlus	a682064
Pregnancy; category	AU: B3 ; US: C (Risk not ruled out) ; ;
Routes of; administration	Oral
ATC code	N04BB01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ; CA: ℞-only ; UK: POM (Prescription only) ; US: ℞-only ;
Pharmacokinetic data
Bioavailability	86–90%
Protein binding	67%
Metabolism	Minimal (mostly to acetyl metabolites)
Elimination half-life	10–31 hours
Excretion	Urine
Identifiers
	IUPAC name Adamantan-1-amine;
CAS Number	768-94-5 ;
PubChem CID	2130;
IUPHAR/BPS	4128;
DrugBank	DB00915 ;
ChemSpider	2045 ;
UNII	BF4C9Z1J53;
KEGG	D07441 ;
ChEBI	CHEBI:2618 ;
ChEMBL	CHEMBL660 ;
ECHA InfoCard	100.011.092
Chemical and physical data
Formula	C10H17N
Molar mass	151.249 g/mol
3D model (JSmol)	Interactive image;
	SMILES NC13CC2CC(CC(C1)C2)C3;
	InChI InChI=1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2 ; Key:DKNWSYNQZKUICI-UHFFFAOYSA-N ;
(verify)

　　[★]

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

「hydrochloride」

　　[★] 塩酸塩、ハイドロクロライド　

[TGA-1] "SYMMETREL® (amantadine hydrochloride)" (PDF). TGA eBusiness Services. NOVARTIS Pharmaceuticals Australia Pty Limited. 29 June 2011. Retrieved 24 February 2014.

[Cochrane_report-2] Crosby, Niall J; Deane, Katherine; Clarke, Carl E (2003). Clarke, Carl E, ed. "Amantadine in Parkinson's disease". Cochrane Database of Systematic Reviews. doi:10.1002/14651858.CD003468.

[USlabel-3] "Amantadine – FDA prescribing information,". Drugs.com. Retrieved 2017-08-28.

[USlabelExtended-4] "Amantadine extended release capsules" (PDF). FDA. August 2017. For label updates, see FDA index page for NDA 208944

[cdc_weekly_report-5] CDC weekly influenza report – week 35, cdc.gov

[6] "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 2008-05-03. Retrieved 2008-05-20.

[JIDResistance-7] 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.

[8] Alves Galvão, MG; Rocha Crispino Santos, MA; Alves da Cunha, AJ (21 November 2014). "Amantadine and rimantadine for influenza A in children and the elderly". The Cochrane Database of Systematic Reviews. 11: CD002745. doi:10.1002/14651858.CD002745.pub4. PMID 25415374.

[9] Braley, TJ; Chervin, RD (Aug 2010). "Fatigue in multiple sclerosis: mechanisms, evaluation, and treatment". Sleep. 33 (8): 1061–7. PMC 2910465. PMID 20815187.

[10] Singhal, KC; Rahman, SZ (2002). "Stevens Johnson Syndrome Induced by Amantadine". Rational Drug Bulletin. 12 (1): 6.

[EndoPharmRXInfo-11] "Symmetrel (Amantadine) Prescribing Information" (PDF). Endo Pharmaceuticals. May 2003. Retrieved 2007-08-02.

[12] Cook, PE; Dermer, SW; McGurk, T (1986). "Fatal overdose with amantadine". Canadian Journal of Psychiatry. 31 (8): 757–8. PMID 3791133.

[13] 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.

[pmid7688826-14] 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.

[pmid18669647-15] 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.

[Austria-Codex-16] Jasek, W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. p. 3962. ISBN 978-3-85200-181-4.

[17] Strömberg, U.; Svensson, T. H. (November 1971). "Further Studies on the Mode of Action of Amantadine". wiley.com. Acta Pharmacologica et Toxicologica, Nordic Pharmacological Society. 30 (3–4): 161–171. doi:10.1111/j.1600-0773.1971.tb00646.x.

[18] ttps://www.ncbi.nlm.nih.gov/mesh/68000547

[Kornhuber1991-19] 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. doi:10.1016/0922-4106(91)90113-v.

[pmid15800186-20] 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.

[PeetersRomieu2004-21] Peeters, Magali; Romieu, Pascal; Maurice, Tangui; Su, Tsung-Ping; Maloteaux, Jean-Marie; Hermans, Emmanuel (2004). "Involvement of the sigma1 receptor in the modulation of dopaminergic transmission by amantadine". European Journal of Neuroscience. 19 (8): 2212–2220. doi:10.1111/j.0953-816X.2004.03297.x. ISSN 0953-816X. PMID 15090047.

[22] Hounshell, David A.; Kenly Smith, John (1988). Science and Corporate Strategy: Du Pont R&D, 1902–1980. Cambridge University Press. p. 469.

[23] "Sales of flu drug by du Pont unit a 'disappointment'". The New York Times. Wilmington, Delaware. October 5, 1982. Retrieved May 19, 2008.

[24] Maugh, T. (1979). "Panel urges wide use of antiviral drug". Science. 206 (4422): 1058–60. doi:10.1126/science.386515. PMID 386515.

[25] 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.

[FDA2017-26] Bastings, Eric. "NDA 208944 Approval Letter" (PDF).

[WashPostBirdFlu-27] Sipress, Alan (2005-06-18). "Bird Flu Drug Rendered Useless". Washington Post. pp. A01. Retrieved 2007-08-02.

[28] Kumar (April 2018). "The emerging influenza virus threat: status and new prospects for its therapy and control". Archives of Virology (4): 831–844. doi:10.1007/s00705-018-3708-y.

[29] Aoki (2007). "Influenza virus susceptibility and resistance to oseltamivir". PMID 17944268.

[LoC-30] "Enforcement Report – Week of September 23, 2015". FDA.gov. US Food and Drug Administration, US Department of Health & Human Services.

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Ethylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 5-DBFPV α-PPP α-PBP α-PHP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

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案内

amantadine hydrochloride

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Medical uses

Parkinson's disease

Influenza

Fatigue in multiple sclerosis

Adverse effects

Mechanism of action

Influenza

Parkinson's disease

History

Veterinary misuse

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