amantadine

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An antiviral drug, C₁₀H₁₇N·HCl, also used in the treatment of Parkinson's disease.

[Alteration of adamantane, a hydrocarbon + –INE².]

Definition

Amantadine is a synthetic antiviral agent that also has strong antiparkinsonian properties. It is sold in the United States under the brand name Symmetrel, and is also available under its generic name.

Purpose

Amantadine is used to treat a group of side effects, called parkinsonian side effects, that include tremors, difficulty walking, and slack muscle tone. These side effects may occur in patients who are taking antipsychotic medications used to treat mental disorders such as schizophrenia. An unrelated use of amantadine is in the treatment of viral infections of some strains of influenza A.

Description

Some medicines, called antipsychotic drugs, that are used to treat schizophrenia and other mental disorders can cause side effects similar to the symptoms of Parkinson's disease. The patient does not have Parkinson's disease, but may experience shaking in muscles while at rest, difficulty with voluntary movements, and poor muscle tone. These symptoms are similar to the symptoms of Parkinson's disease.

One way to eliminate these undesirable side effects is to stop taking the antipsychotic medicine. Unfortunately, the symptoms of the original mental disorder usually come back; in most cases, simply stopping the antipsychotic medication is not a reasonable option. Some drugs such as amantadine that control the symptoms of Parkinson's disease also control the parkinsonian side effects of antipsychotic medicines.

Amantadine works by restoring the chemical balance between dopamine and acetylcholine, two neurotransmitter chemicals in the brain. Taking amantadine along with the antipsychotic medicine helps to control symptoms of the mental disorder, while reducing parkinsonian side effects. Amantadine is in the same family of drugs commonly known as anticholinergic drugs, including biperiden and trihexyphenidyl.

Recommended dosage

Amantadine is available in 100 mg tablets and capsules, as well as a syrup containing 50 mg of amantadine in each teaspoonful. For the treatment of drug-induced parkinsonian side effects, amantadine is usually given in a dose of 100 mg orally twice a day. Some patients may need a total daily dose as high as 300 mg. Patients who are taking other antiparkinsonian drugs at the same time may require lower daily doses of amantadine (e.g., 100 mg daily).

People with kidney disease or who are on hemodialysis must have their doses lowered. In these patients, doses may range from 100 mg daily to as little as 200 mg every seven days.

Precautions

Amantadine increases the amount of the dopamine (a central nervous system stimulant) in the brain. Because of this, patients with a history of epilepsy or other seizure disorders should be carefully monitored while taking this drug. This is especially true in the elderly and in patients with kidney disease. Amantadine may cause visual disturbances and affect mental alertness and coordination. People should not operate dangerous machinery or motor vehicles while taking this drug.

Side effects

Five to 10% of patients taking amantadine may experience nervous system side effects, including:

• dizziness or lightheadedness
• insomnia
• nervousness or anxiety
• impaired concentration

One to 5% of patients taking amantadine may experience other nervous system side effects, including:

• irritability or agitation
• depression
• confusion
• lack of coordination
• sleepiness or nightmares
• fatigue
• headache

In addition, up to 1% of patients may experience hallucinations, euphoria (excitement), extreme forgetfulness, aggressive behavior, personality changes, or seizures. Seizures are the most serious of all the side effects associated with amantadine.

Gastrointestinal side effects may also occur in patients taking amantadine. Five to 10% of people taking this drug experience nausea and up to 5% have dry mouth, loss of appetite, constipation, and vomiting. In most situations, amantadine may be continued and these side effects treated symptomatically.

One to 5% of patients taking amantadine have also reported a bluish coloring of their skin (usually on the legs) that is associated with enlargement of the blood vessels (livedo reticularis). This side effect usually appears within one month to one year of starting the drug and subsides within weeks to months after the drug is discontinued. People who think they may be experiencing this or other side effects from any medication should tell their physician.

Interactions

Taking amantadine along with other drugs used to treat parkinsonian side effects may cause increased confusion or even hallucinations. The combination of amantadine and central nervous system stimulants (e.g., amphetamines or decongestants) may cause increased central nervous stimulation or increase the likelihood of seizures.

Resources

BOOKS

American Society of Health-System Pharmacists. AHFS Drug Information 2002. Bethesda: American Society of Health-System Pharmacists, 2002.

DeVane, C. Lindsay, PharmD. "Drug Therapy for Psychoses." In Fundamentals of Monitoring Psychoactive Drug Therapy. Baltimore: Williams and Wilkins, 1990.

Jack Raber, PharmD

An antiviral that prevents uncoating and replication of the influenza A virus; most effectively used in the early stages of exposure.

Brand names: Symmetrel®

Chemical formula:

Drug Forms:
• Amantadine capsules or tablets (below)
• Amantadine Hydrochloride Oral tablet
• Amantadine Hydrochloride Oral capsule
• Amantadine Hydrochloride Oral solution

Español:
• Cápsulas o tabletas de amantadina
• Amantadina Clorhidrato, Tableta oral
• Amantadina Clorhidrato, Cápsula oral
• Clorhidrato de Amantadina, Solución oral

Amantadine capsules or tablets

What are amantadine capsules or tablets?

AMANTADINE (Symmetrel®) prevents or treats certain influenza (flu) infections. It is not an effective treatment for colds or other viruses. Amantadine can also improve muscle control and reduce muscle stiffness in patients with Parkinson's disease or similar movement disorders. Generic amantadine capsules are available.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• closed-angle glaucoma
• depression or other mental illness
• eczema
• heart or circulation problems
• kidney disease
• liver disease
• low blood pressure
• seizures (convulsions)
• an unusual or allergic reaction to amantadine, rimantadine, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I take this medicine?

Take amantadine capsules or tablets by mouth. Follow the directions on the prescription label. Swallow whole with a full glass of water. If it upsets your stomach you can take amantadine with food. Take your doses at regular intervals. Do not take your medicine more often than directed. Finish the full course prescribed by your prescriber or health care professional even if you think your condition is better. Do not stop taking except on your prescriber's advice.

Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.

What if I miss a dose?

What drug(s) may interact with amantadine?

• alcohol
• bupropion
• caffeine
• haloperidol
• hydrochlorothiazide, HCTZ; triamterene
• medicines for hay fever and other allergies
• medicines for depression or other mental illness
• metoclopramide
• quinidine
• quinine
• sulfamethoxazole; trimethoprim, SMX-TMP

Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.

What should I watch for while taking amantadine?

Let your prescriber or health care professional know if your symptoms do not improve in a few days.

You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how amantadine affects you. To reduce the risk of dizzy or fainting spells, do not sit or stand up quickly, especially if you are an older patient. Alcohol can make you more drowsy and dizzy, increase confusion and lightheadedness. Avoid alcoholic drinks.

If you are taking amantadine for a movement disorder, do not suddenly stop taking it. You may get muscle stiffness, paralysis, confusion, or find it difficult to pass urine.

If you are taking amantadine for Parkinson's disease, be careful not to overdo physical activity as your condition improves. Gradually increase activity so that your body has time to adjust.

Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water will help. Brush and floss teeth regularly and carefully to avoid problems with the mouth and gums.

What side effects may I notice from taking amantadine?

Side effects that you should report to your prescriber or health care professional as soon as possible:
• changes in vision
• depression or thoughts of suicide
• difficulty passing urine
• fainting spells or lightheadedness
• hallucinations (seeing things that are not really there)
• movement difficulties
• purplish spots or network on the skin
• seizures (convulsions)
• swelling of the feet or legs

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• anxiety, irritability, nervousness
• diarrhea or constipation
• difficulty sleeping, or nightmares
• drowsiness
• dry mouth
• headache
• loss of appetite
• nausea or vomiting
• unusual tiredness

Where can I keep my medicine?

Keep out of the reach of children in a container that small children cannot open.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

Amantadine
Systematic (IUPAC) name
adamantan-1-amine
Identifiers
CAS number	768-94-5
ATC code	N04BB01
PubChem	2130
DrugBank	APRD00787
ChemSpider	2045
Chemical data
Formula	C10H17N
Mol. mass	151.249 g/mol
Synonyms	1-Adamantylamine
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.

Apart from medical uses, this compound is useful as a building block, allowing the insertion of an adamantyl group.

Contents 1 Preparation 2 Dosage 3 Uses 3.1 Approved 3.2 Off-label uses 4 Side effects 5 Mechanism of action 6 Misuse 7 Declining effectiveness 8 References 9 See also

Preparation

Amantadine may be prepared by reacting adamantane with bromine or nitric acid to give the bromide or nitroester at the 1- position. Reaction of either compound with acetonitrile affords the acetamide, which is hydrolyzed to give 1-adamantylamine:^[1]

Dosage

A starting dose is often 100 mg once daily. Most influenza A strains are resistant to amantadine, so a failure at this dose is likely due to resistance and not underdosing. For its anti-Parkinsonian effects, a starting dose of 300 mg once daily is normal, but can be increased up to 400 mg.

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 A^[2][3][4][5] 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

Amantadine is frequently used to treat the characteristic fatigue often experienced by patients with multiple sclerosis.^[6] Additionally, there have been anecdotal reports that low-dose amantadine has been successfully used to treat ADHD.^[7] Amantadine has also been shown to relieve SSRI-induced sexual dysfunction.^[8][9][10]

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,^[11] although this psychiatric adverse event is relatively rare. Nevertheless, 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.^[12]

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 mechanisms for amantadine's antiviral and antiparkinsonian effects appear unrelated.

• The mechanism of Amantadine's antiviral activity involves interference with a viral protein, M2 (an ion channel),^[13] which is required for the viral particle to become "uncoated" once taken inside a cell by endocytosis.

• The mechanism of its antiparkinsonian effect is poorly understood. 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^[14] as well as an anticholinergic.

Misuse

In 2005, Chinese poultry farmers were reported to have used amantadine to protect birds against avian influenza.^[15] 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.^[15] 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 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.

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 amantadine resistance.^[16]

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.^[17] Among some Asian countries, A/H3N2 and A/H1N1 resistance has reached 100%.^[18]

References

1. ^ I. K. Moiseev, R. I. Doroshenko and V. I. Ivanova (1976). "Synthesis of amantadine via the nitrate of 1-adamantanol". Pharmaceutical Chemistry Journal 10 (4): 450-451. doi:10.1007/BF00757832. 
2. ^ David A. Hounshell and John Kenly Smith, "Science and Corporate Strategy: Du Pont R&D, 1902-1980", 1988, Cambridge University Press, p. 469. http://books.google.com/books?id=6ld0K9VNpmIC
3. ^ "SALES OF FLU DRUG BY DU PONT UNIT A 'DISAPPOINTMENT'" (Last accessed May 19, 2008.) October 5, 1982, The New York Times.
4. ^ 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)
5. ^ 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)
6. ^ Cohen RA, Fisher M. Amantadine treatment of fatigue associated with MS. Arch Neurol 1989;46:676–680
7. ^ Hallowell, Edward M. and John J. Ratey, Delivered from Distraction: Getting the Most out of Life with Attention Deficit Disorder (2005), pp. 253-5.
8. ^ Shrivastava RK, Shrivastava S, Overweg N, Schmitt M (February 1995). "Amantadine in the treatment of sexual dysfunction associated with selective serotonin reuptake inhibitors". Journal of clinical psychopharmacology 15 (1): 83–4. PMID 7714234. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0271-0749&volume=15&issue=1&spage=83. 
9. ^ Balogh S, Hendricks SE, Kang J (June 1992). "Treatment of fluoxetine-induced anorgasmia with amantadine". The Journal of clinical psychiatry 53 (6): 212–3. PMID 1607353. 
10. ^ 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. PMID 9292832. 
11. ^ Endo Pharmaceuticals (May 2003) (PDF). Symmetrel (Amantadine) Prescribing Information. http://www.symmetrel.com/PDF/symmetrel_pack_insert.pdf. Retrieved on 2007-08-02. 
12. ^ Cook et al., "Fatal overdose with amantadine". Can. J. Psychiatry (Nov 1986); 31(8), pp. 757-758.
13. ^ Wang C, Takeuchi K, Pinto LH, Lamb RA (September 1993). "Ion channel activity of influenza A virus M2 protein: characterization of the amantadine block". Journal of virology 67 (9): 5585–94. PMID 7688826. PMC: 237962. http://jvi.asm.org/cgi/pmidlookup?view=long&pmid=7688826. 
14. ^ Blanpied TA, Clarke RJ, Johnson JW (March 2005). "Amantadine inhibits NMDA receptors by accelerating channel closure during channel block". The Journal of neuroscience : the official journal of the Society for Neuroscience 25 (13): 3312–22. doi:10.1523/JNEUROSCI.4262-04.2005. PMID 15800186. http://www.jneurosci.org/cgi/pmidlookup?view=long&pmid=15800186. 
15. ^ ^{a b} Sipress, Alan (2005-06-18). "Bird Flu Drug Rendered Useless". Washington Post. pp. A01. http://www.washingtonpost.com/wp-dyn/content/article/2005/06/17/AR2005061701214.html. Retrieved on 2007-08-02. 
16. ^ 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. BL Shelfmark 4689.000000. ISSN 0098-7484. OCLC 194229372. PMID 16456087. http://jama.ama-assn.org/cgi/content/full/295.8.joc60020v1. Retrieved on 2008-05-20. 
17. ^ "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. http://www.cdc.gov/flu/han011406.htm. Retrieved on 2008-05-20. 
18. ^ 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 A(H3N2) and A(H1N1) Viruses Isolated Worldwide". Journal of Infectious Diseases 196 (2): 249–257. doi:10.1086/518936. http://www.journals.uchicago.edu/doi/full/10.1086/518936. Retrieved on 2008-05-19. 

See also

• Rimantadine
• Tromantadine

v • d • e Dopaminergics Receptor Ligands Agonists Benzazepines: Fenoldopam • SKF 38393 • SKF 82958; Ergot-derivatives: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • LSD • Pergolide; Dihydrexidine-derivatives: A-86929 • Dihydrexidine • Dinapsoline • Dinoxyline • Doxathrine; Morphine-derivatives: Apomorphine • Propylnorapomorphine; Piperazines: Aripiprazole • Piribedil • WAY-100,635; Others: A-412,997 • Aplindore • Memantine • Pramipexole • Pukateine • Quinpirole • RDS-127 • Ropinirole • Rotigotine Antagonists Typical Antipsychotics: Acepromazine • Azaperone • Benperidol • Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol • Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine • Mesoridazine • Methotrimeprazine • Molindone • Penfluridol • Perazine • Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine • Sulforidazine • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; Atypical Antipsychotics: Amisulpride • Asenapine • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Perospirone • Quetiapine • Risperidone • Sertindole • Sulpiride • Ziprasidone • Zotepine; Antiemetics: Alizapride • Bromopride • Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others: Amoxapine • Blonanserin • Buspirone • Butaclamol • N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline • Eticlopride • Fananserin • Mosapramine • Nafadotride • Nemonapride • Nuciferine • Raclopride • Remoxipride • SB-277,011-A • SCH 23390 • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine • Tiapride • UH-232 • Yohimbine Reuptake Inhibitors Plasmalemmal DAT Inhibitors Piperazines: DBL-583 • GBR-12935 • Nefazodone • Vanoxerine; Piperidines: BTCP • Desoxypipradrol • Dextromethylphenidate • Ethylphenidate • HDMP-28 • Methylphenidate • Phencyclidine • Pipradrol; Pyrovalerones: MDPV • Pyrovalerone; Tropanes: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane • Lometopane • RTI-121 • RTI-126 • RTI-150 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Amfonelic Acid • Amineptine • Benztropine • Bromantane • BTQ • BTS 74,398 • Bupropion • Cypenamine • Diclofensine • Dimethocaine • Diphenylprolinol • Dizocilpine • DOV 102,677 • DOV 21,947 • DOV 216,303 • Ethcathinone • Fencamfamine • GYKI-52895 • Indatraline • Ketamine • Lefetamine • LR-5182 • Manifaxine • Mazindol • Medifoxamine • Mesocarb • Nisoxetine • Nomifensine • NS2359 • O-2172 • Prolintane • Radafaxine • SEP-225289 • SEP-227162 • Sibutramine • Tametraline • Tripelennamine TRPC6 Activators Adhyperforin • Hyperforin Vesicular VMAT Inhibitors Ibogaine • Reserpine • Tetrabenazine Releasing Agents Alkylamines: Cyclopentamine • Propylhexedrine; Aminopropanes: Indanylaminopropane • Naphthylaminopropane; Oxazolines: 4-Methylaminorex • Aminorex • Pemoline; Phenethylamines: 4-Fluoroamphetamine • 4-Fluoromethamphetamine • Amphetamine • Amphetaminil • Amfepentorex • Benzphetamine • Butylone • Cathine • Cathinone • Clobenzorex • Dextroamphetamine • Diethylcathinone • Dimethylamphetamine • Dimethylcathinone • Ethylamphetamine • Ethylone • Fenethylline • Fenproporex • Flephedrone • Furfenorex • MBDB • MDA • MDEA • MDMA • Mefenorex • Mephedrone • Methamphetamine • Methcathinone • Methylone • Phendimetrazine • Phenethylamine • Phenmetrazine • PMA • PMEA • PMMA • Propylamphetamine • Tyramine • Xylopropamine; Piperazines: BZP • MBZP • MeOPP; Others: 4-Benzylpiperidine • Zylofuramine Enzyme Inhibitors Anabolism PAH Inhibitors 3,4-Dihydroxystyrene TH Inhibitors 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone AAAD Inhibitors Benserazide • Carbidopa Catabolism MAO Inhibitors Nonselective: Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Phenelzine • Pheniprazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline COMT Inhibitors Entacapone • Tolcapone DBH Inhibitors Disulfiram • Nepicastat • Tropolone Others Precursors L-Phenylalanine • L-Tyrosine • L-DOPA Cofactors Iron • Tetrahydrobiopterin • Vitamin B3 (Niacin/Nicotinamide/NADPH) • Vitamin B6 (Pyridoxine/Pyridoxamine/Pyridoxal 5-Phosphate) • Vitamin B9 (Folic Acid/Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc Others Activity Enhancers: BPAP • PPAP; Others: Amantadine • Memantine • Rimantadine

v • d • e Glutamatergics Ionotropic NMDA Agonists; Glutamate/main site/competitive agonists; Aspartate • Glutamate • Homoquinolinic acid • Ibotenic acid • NMDA • Quinolinic acid • Tetrazolylglycine; Glycine site agonists; ACPC • D-Alanine • D-Cycloserine • D-Fluoroalanine • D-Serine • Glycine • HA-966 • L-687,414 • Milacemide; Polyamine site agonists; Spermidine • Spermine Antagonists; Competitive antagonists; AP5 • AP7 • CGP-37849 • CGP-39551 • CGP-39653 • CGP-40116 • CGS-19755 • CPP/CPPene (Midafotel) • LY-233,053 • LY-235,959 • LY-274,614 • MDL-100,453 • NPC-17,742 • PEAQX • Perzinfotel • PBPD • PPDA • SDZ-220581 • Selfotel; Noncompetitive antagonists; Aptiganel • CNS-1102 • Dizocilpine (MK-801) • FPL-12495 • FR-115,427 • Gacyclidine • Hodgkinsine • HU-211 • Indantadol • Psychotridine • Remacemide; Uncompetitive channel blockers; 2-MDP • 8a-Phenyldecahydroquinoline • N-(3,3-Diphenylpropyl)glycinamide • Amantadine • Budipine • Delucemine • Dexoxadrol • Dextromethorphan • Dextrorphan • Endopsychosin • Etoxadrol • Eticyclidine • Ibogaine • Ketamine • Ketobemidone • Loperamide • Memantine • Meperidine (Pethidine) • Methadone • NEFA • Neramexane • Nitrous oxide • Orphenadrine • Phencyclidine • Propoxyphene • Rhynchophylline • Riluzole • Rolicyclidine • Tenocyclidine • Tiletamine • Tramadol • Xenon; Glycine site antagonists; ACPC • 7-Chlorokynurenate • ACEA-1021 • ACEA-1328 • Carisoprodol • CGP-39653 • DCKA • Felbamate • Gavestinel • GV-150,526 • GV-196,771A • HA-966 • Kynurenic acid • L-689,560 • L-701,324 • Lacosamide • LU-73,068 • MDL-105,519 • Meprobamate • MRZ 2/576 • PNQX • ZD-9379; NR2B subunit antagonists; Besonprodil • CP-101,606 • Eliprodil • Ifenprodil • Ro8-4304 • Ro25-6981 • Traxoprodil; Polyamine site antagonists; Arcaine • Co 101676 • Diethylenetriamine • Huperzine A • Pentamidine • Putrescine • Ro 25-6981; Indirect antagonists; Lubeluzole; Other antagonists; Ethanol • Magnesium • Zinc AMPA Agonists; 5-Fluorowillardiine • AMPA • Domoic acid • Quisqualic acid; Positive allosteric modulators; Aniracetam • Cyclothiazide • CX-516 • CX-546 • CX-614 • CX-691 • CX-717 • IDRA-21 • LY-392,098 • LY-404,187 • LY-451,395 • LY-451,646 • LY-503,430 • Oxiracetam • PEPA • Piracetam • Pramiracetam Antagonists; ATPO • CNQX • DNQX • GYKI-52466 • NBQX • Perampanel • Tezampanel (LY-293,558); Negative allosteric modulators; GYKI-53,655 Kainate Agonists; 5-Iodowillardiine • ATPA • Domoic acid • Kainic acid • LY-339,434 • SYM-2081 Antagonists; CNQX • DNQX • LY-382,884 • NBQX • NS102 • UBP-302; Negative allosteric modulators; NS-3763 Metabotropic Group I Agonists; Unselective; ACPD • Dihydroxyphenylglycine • Quisqualic acid; mGlu1 selective; Ro01-6128; mGlu5 selective; CDPPB • CHPG • DFB Antagonists; Unselective; MCPG; mGlu1 selective; BAY 36-7620 • CPCCOEt • LY-367,385; mGlu5 selective; DMeOB • Fenobam • LY-344,545 • MPEP • MTEP Group II Agonists; Unselective; CBiPES • DCG-IV • Eglumegad (LY-354,740) • LY-379,268 • LY-404,039; mGlu2 selective; BINA • LY-487,379 Antagonists; Unselective; APICA • EGLU • LY-307,452 • LY-341,495 • MCCG; mGlu2 selective; PCCG-4; mGlu3 selective; CECXG Group III Agonists; Unselective; AP4; mGlu4 selective; PHCCC • VU-001,171 • VU-0155,041; mGlu7 selective; AMN082; mGlu8 selective; DCPG Antagonists; Unselective; CPPG • MAP4 • MSOP • MPPG • MTPG • UBP-1112; mGlu7 selective; MMPIP Transporter Inhibitors EAATs Dihydrokainic acid • PDC • WAY-213,613 VGluTs 7-Chlorokynurenic acid • Evans blue TRPC6s Adhyperforin • Hyperforin

v • d • e RNA virus antivirals (primarily J05, also S01AD and D06BB) Hepatitis C protease inhibitor (Boceprevir†, Telaprevir†) Picornavirus viral entry: Pleconaril† Anti-influenza agents Arbidol adamantane derivatives/M2 inhibitors (Amantadine, Rimantadine) neuraminidase inhibitors/release phase (Oseltamivir, Zanamivir, Peramivir†) Multiple/general Interferon Interferon alfa-2b · Peginterferon alfa-2a Multiple/unknown Ribavirin#/Taribavirin† #WHO-EM. †Undergoing clinical trials, not FDA approved. ‡Withdrawn from market. §Development halted.

v • d • e Influenza General topics Research - Vaccine - Treatment - Genome sequencing - Reassortment - Superinfection - Season Influenza viruses Orthomyxoviridae - Influenza A - Influenza B - Influenza C Influenza A virus Subtypes H1N1 - H1N2 - H2N2 - H2N3 - H3N1 - H3N2 - H3N8 - H5N1 - H5N2 - H5N3 - H5N8 - H5N9 - H7N1 - H7N2 - H7N3 - H7N4 - H7N7 - H9N2 - H10N7 H1N1        Pandemics 1918 flu pandemic (Spanish flu) - 2009 flu pandemic Science 2009 A/H1N1 H5N1 Science Genetic structure - Transmission and infection - Global spread - Clinical Trials - Human mortality - Social impact - Pandemic preparation         Outbreaks Croatia (2005) - India (2006) - UK (2007) - West Bengal (2008) Treatments Antiviral drugs Arbidol - adamantane derivatives (Amantadine, Rimantadine) - neuraminidase inhibitors (Oseltamivir, Peramivir, Zanamivir) Experimental (Peramivir) Flu vaccines FluMist - Fluzone Influenza epidemics & pandemics        Pandemics Russian flu (1889–1890) - Spanish Flu - Asian Flu - Hong Kong Flu - 2009 flu pandemic Epidemics Russian flu (1977–1978) - Fujian flu (H3N2) Non-human Mammals Canine influenza - Cat influenza - Equine influenza (2007 Australian outbreak) - Swine influenza Non-mammals Avian influenza - Fujian flu (H5N1) Related Influenza-like illness

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