Rimantadine

Brand names: Flumadine®

Chemical formula:

Drug Forms:
• Rimantadine Hydrochloride Oral tablet (below)
• Rimantadine tablets
• Rimantadine oral syrup
• Rimantadine Hydrochloride Oral syrup

Espa�ol:
• Clorhidrato de rimantadina, Tableta oral
• Tabletas de rimantadina
• Jarabe oral de rimantadina
• Clorhidrato de rimantadina, Jarabe oral

Rimantadine Hydrochloride Oral tablet

What is this medicine?

RIMANTADINE (ri MAN ta deen) is an antiviral medicine. It is used to prevent and treat a specific type of flu called influenza A. It will not work for colds, other types of flu, or other viral infections.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

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

They need to know if you have any of these conditions:
•kidney disease
•liver disease
•seizures
•taken or scheduled to take intranasal flu vaccine within 2 weeks
•an unusual or allergic reaction to rimantadine, amantadine, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. Take your medicine at regular intervals. Do not take your medicine more often than directed. Take all of your medicine as directed even if you think your are better. Do not skip doses or stop your medicine early.

Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for children as young as 1 year old for selected conditions, precautions do apply.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

•acetaminophen
•aspirin
•cimetidine
•intranasal flu vaccine

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Tell your doctor or healthcare professional if your symptoms do not start to get better or if they get worse.

You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how this medicine affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•breathing difficulties
•chest pain or palpitations
•dizziness or fainting
•swelling of the legs or ankles
•seizures
•unusually weak or tired

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•difficulty sleeping
•dizziness
•dry mouth
•headache
•loss of appetite
•nausea, vomiting
•stomach pain

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 15 degrees and 30 degrees C (59 degrees and 86 degrees F). 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.

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A synthetic antiviral agent with activity against RNA viruses.

Rimantadine

Systematic (IUPAC) name
(RS)-1-(1-adamantyl)ethanamine
Clinical data
Trade names	Flumadine
AHFS/Drugs.com	monograph
MedlinePlus	a698029
Pregnancy cat.	C (United States)
Legal status	℞-only (U.S.)
Routes	Oral
Pharmacokinetic data
Bioavailability	well absorbed
Protein binding	40%
Metabolism	Hepatic hydroxylation and glucuronidation
Half-life	25.4 ± 6.3 hours
Excretion	Renal
Identifiers
CAS number	13392-28-4
ATC code	J05AC02
PubChem	CID 5071
DrugBank	APRD01219
ChemSpider	4893 Y
UNII	0T2EF4JQTU Y
KEGG	D08483 Y
ChEMBL	CHEMBL959 Y
Chemical data
Formula	C12H21N
Mol. mass	179.302 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3 Y Key:UBCHPRBFMUDMNC-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

Rimantadine (INN, sold under the trade name Flumadine) is an orally administered antiviral drug^[1] used to treat, and in rare cases prevent, influenzavirus A infection. When taken within one to two days of developing symptoms, rimantadine can shorten the duration and moderate the severity of influenza. Both rimantadine and the similar drug amantadine are derivates of adamantane. Rimantadine was approved by the Food and Drug Administration (FDA) in 1994.

According to the CDC, 100% of seasonal H3N2 and 2009 pandemic flu samples tested have shown resistance to rimantadine and it is no longer recommended to prescribe for treatment of the flu.^[2]

Contents 1 History 2 Clinical usage 2.1 Drug interactions 2.2 Possible side effects 3 References 4 External links

History

Rimantadine was discovered in 1963^[3][4][5] and patented in 1965 in the USA by William W. Prichard in Du Pont & Co., Wilmington, Delaware (US patent on new chemical compound № 3352912, 1965 and on the first method of synthesis № 3592934, 1967).^[6][5][7] Prichard's methods of synthesis of rimantadine from the corresponding ketone oxime were based on its reduction with lithium aluminum hydride.

Clinical usage

Rimantadine is believed to inhibit influenza's viral replication, possibly by preventing the uncoating of the virus's protective shells, which are the envelope and capsid. Genetic studies suggest that the virus M2 protein, an ion channel specified by virion M2 gene, plays an important role in the susceptibility of influenza A virus to inhibition by rimantadine. Resistance to rimantadine can occur as a result of an amino acid substitutions at certain locations in the transmembrane region of M2. This prevents binding of the antiviral to the channel.^[8]

Rimantadine, like its antiviral cousin amantadine, possesses some NMDA antagonistic properties and is used as an antiparkinsonic drug (i.e., in the treatment of Parkinson's disease). However, neither rimantadine nor amantadine are preferred agents for this therapy and are generally reserved for cases of the disease which are less responsive to front-line treatments.

Drug interactions

Taking paracetamol (acetaminophen e.g. Tylenol) or acetylsalicylic acid (aspirin) while taking rimantadine is known to reduce the body's uptake of rimantadine by approximately 12%.^[9] Cimetidine also affects the body's uptake of rimantadine.

Possible side effects

Rimantadine can produce gastrointestinal and central nervous system adverse effects. Approximately 6% of patients (compared to 4% of patients taking a placebo) reported side effects at a dosage of 200 mg/d.^[10] Common side effects include:

• nausea
• upset stomach
• nervousness
• tiredness
• lightheadedness
• trouble sleeping
• difficulty concentrating

References

1. ^ Govorkova EA, Fang HB, Tan M, Webster RG (December 2004). "Neuraminidase Inhibitor-Rimantadine Combinations Exert Additive and Synergistic Anti-Influenza Virus Effects in MDCK Cells". Antimicrobial agents and chemotherapy 48 (12): 4855–63. doi:10.1128/AAC.48.12.4855-4863.2004. PMC 529183. PMID 15561867. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=15561867. 
2. ^ http://www.cdc.gov/mmwr/preview/mmwrhtml/rr6001a1.htm
3. ^ US patent 3352912 to W. W. Prichard
4. ^ United States Patent № 4551552: Process for preparing rimantadine: Rimantadine and related compounds useful as antivirals were first described by Prichard in U.S. Pat. Nos. 3,352,912 and 3,592,934. Both patents describe the preparation of rimantadine from the corresponding ketone oxime by reduction with lithium aluminum hydride.
5. ^ ^{a b} Rimantadine
6. ^ United States Patent № 4551552: Process for preparing rimantadine
7. ^ D. M. Zlydnikov, O. I. Kubar, T. P. Kovaleva, L. E. Kamforin. Study of Rimantadine in the USSR: A Review of the Literature. Clinical Infectious Diseases 3:408-421, p.408.
8. ^ Jing X, Ma C, Ohigashi Y, et al. (August 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2492755. 
9. ^ "fda.gov". http://www.fda.gov/cder/drug/antivirals/influenza/flumadine.htm. Retrieved 2008-11-05. ^{[dead link]}
10. ^ "CDC - Influenza (Flu) | Antivirals: Side-Effects | REMOVED!". http://www.cdc.gov/flu/professionals/treatment/side-effects.htm. Retrieved 2008-11-05. 

External links

• U.S. FDA press release announcing rimantadine's approval
• U.S. Center for Drug Evaluation and Research rimantadine description
• U.S. NIH rimantadine description
• U.S. CDC flu anti-viral treatment information

v · d · eRNA virus antivirals (primarily J05, also S01AD and D06BB) Hepatitis C protease inhibitors (Boceprevir, Telaprevir) Picornavirus viral entry: Pleconaril† Anti-influenza agents Arbidol adamantane derivatives/M2 inhibitors (Amantadine, Rimantadine) neuraminidase inhibitors/release phase (Oseltamivir, Zanamivir, Peramivir†, Laninamivir†) Multiple/general Interferon Interferon alfa-2b • Peginterferon alfa-2a Multiple/unknown Ribavirin#/Taribavirin† #WHO-EM. ‡Withdrawn from market. Clinical trials: †Phase III. §Never to phase III M: VIR virs(prot)/clss cutn/syst (hppv/hiva, infl/zost/zoon)/epon drugJ(dnaa, rnaa, rtva, vacc)

v · d · eInfluenza 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 (Swine flu) Science 2009 A/H1N1 H5N1         Outbreaks Croatia (2005) - India (2006) - UK (2007) - West Bengal (2008) Science Genetic structure - Transmission and infection - Global spread - Clinical Trials - Human mortality - Social impact - Pandemic preparation Treatments Antiviral drug Arbidol - adamantane derivatives (Amantadine, Rimantadine) - neuraminidase inhibitors (Oseltamivir, Laninamivir, Peramivir, Zanamivir) Experimental (Peramivir) Flu vaccines FluMist - Fluzone Influenza epidemics and 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 M: VIR virs(prot)/clss cutn/syst (hppv/hiva, infl/zost/zoon)/epon drugJ(dnaa, rnaa, rtva, vacc)

v · d · eDopaminergics  Receptor ligands Agonists Adamantanes: Amantadine • Memantine • Rimantadine; Aminotetralins: 7-OH-DPAT • 8-OH-PBZI • Rotigotine • UH-232; Benzazepines: 6-Br-APB • Fenoldopam • SKF-38,393 • SKF-77,434 • SKF-81,297 • SKF-82,958 • SKF-83,959; Ergolines: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • LSD • Pergolide; Dihydrexidine derivatives: 2-OH-NPA • A-86,929 • Ciladopa • Dihydrexidine • Dinapsoline • Dinoxyline • Doxanthrine; Others: A-68,930 • A-77,636 • A-412,997 • ABT-670 • ABT-724 • Aplindore • Apomorphine • Aripiprazole • Bifeprunox • BP-897 • CY-208,243 • Dizocilpine • Etilevodopa • Flibanserin • Ketamine • Melevodopa • Modafinil • Pardoprunox • Phencyclidine • PD-128,907 • PD-168,077 • PF-219,061 • Piribedil • Pramipexole • Propylnorapomorphine • Pukateine • Quinagolide • Quinelorane • Quinpirole • RDS-127 • Ro10-5824 • Ropinirole • Rotigotine • Roxindole • Salvinorin A • SKF-89,145 • Sumanirole • Terguride • Umespirone • WAY-100,635 Antagonists Typical antipsychotics: Acepromazine • Azaperone • Benperidol • Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol • Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine • Mesoridazine • Methotrimeprazine • Nemonapride • Penfluridol • Perazine • Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine • Sulforidazine • Sulpiride • Sultopride • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; 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Pyrrolidines: Diphenylprolinol • Methylenedioxypyrovalerone (MDPV) • Naphyrone • Prolintane • Pyrovalerone; Tropanes: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (123I) • Iometopane • RTI-112 • RTI-113 • RTI-121 • RTI-126 • RTI-150 • RTI-177 • RTI-229 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Adrafinil • Armodafinil • Amfonelic acid • Amineptine • Benzatropine (Benztropine) • Bromantane • BTQ • BTS-74,398 • Bupropion (Amfebutamone) • Ciclazindol • Diclofensine • Dimethocaine • Diphenylpyraline • Dizocilpine • DOV-102,677 • DOV-21,947 • DOV-216,303 • Etybenzatropine (Ethylbenztropine) • EXP-561 • Fencamine • Fencamfamine • Fezolamine • GYKI-52,895 • Indatraline • Ketamine • Lefetamine • Levophacetoperane • LR-5182 • Manifaxine • Mazindol • Medifoxamine • Mesocarb • Modafinil • Nefopam • Nomifensine • NS-2359 • O-2172 • Pridefrine • Propylamphetamine • Radafaxine • SEP-225,289 • SEP-227,162 • Sertraline • Sibutramine • Tametraline • Tedatioxetine  • Tripelennamine Vesicular VMAT inhibitors Deserpidine • Ibogaine • Reserpine • Tetrabenazine  Releasing agents Morpholines: Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine; Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-CAB • 4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • Alfetamine • Amfecloral • Amfepentorex • Amfepramone • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Methylphenethylamine (β-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • D-Deprenyl • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, metamfepramone) • Ethcathinone (Ethylpropion) • Ethylamphetamine • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Famprofazone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • Lophophine (Homomyristicylamine) • Mefenorex • Mephedrone • Methamphetamine (Desoxyephedrine, Methedrine; 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Others: 2-Amino-1,2-dihydronaphthalene (2-ADN) • 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 4-Benzylpiperidine (4-BP) • 5-IAI • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Indanylaminopropane (IAP) • Indanorex • Isometheptene • Methylhexanamine • Naphthylaminopropane (NAP) • Octodrine • Phthalimidopropiophenone • Propylhexedrine (Levopropylhexedrine) • Tuaminoheptane (Tuamine)  Enzyme inhibitors Anabolism PAH inhibitors 3,4-Dihydroxystyrene TH inhibitors 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone AAAD/DDC inhibitors Benserazide • Carbidopa • Genistein • Methyldopa Catabolism MAO inhibitors Nonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone • Hydralazine • Indantadol • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide • Octamoxin • Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A selective: Amiflamine • Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids • Methylene Blue • Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone • Tyrima; MAO-B selective: D-Deprenyl • L-Deprenyl (Selegiline) • Ladostigil • Lazabemide • Milacemide • Pargyline • Rasagiline • Safinamide COMT inhibitors Entacapone • Tolcapone DBH inhibitors Disulfiram • Dopastin • Fusaric acid • Nepicastat • Tropolone  Others Precursors L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) Cofactors Ferrous iron (Fe2+) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal phosphate) • Vitamin B9 (Folic acid → Tetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+) Others Activity enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Toxins: Oxidopamine (6-Hydroxydopamine) List of dopaminergic drugs

v · d · eAntiparkinson agents (N04) Dopaminergics DA precursors/prodrugs Etilevodopa • Droxidopa • Levodopa# • Melevodopa DA receptor agonists Aplindore • Apomorphine • Bromocriptine • Cabergoline • Ciladopa • Dihydroergocryptine • Lisuride • Pardoprunox • Pergolide • Piribedil • Pramipexole • Ropinirole • Rotigotine MAO-B inhibitors Ladostigil • Lazabemide • Mofegiline • Pargyline • Rasagiline • Selegiline COMT inhibitors Entacapone • Tolcapone Aromatic L-amino acid decarboxylase inhibitors Benserazide • Carbidopa# • Methyldopa Anticholinergics Benzatropine • Biperiden# • Bornaprine • Chlorphenoxamine • Cyrimine • Dexetimide • Dimenhydrinate • Diphenhydramine • Etanautine • Etybenzatropine • Mazaticol • Metixene • Orphenadrine • Phenglutarimide • Piroheptine • Procyclidine • Profenamine • Trihexyphenidyl • Tropatepine Others Amantadine • Budipine • Memantine • Rimantadine #WHO-EM. ‡Withdrawn from market. Clinical trials: †Phase III. §Never to phase III M: CNS anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr proc, drug(N1A/2AB/C/3/4/7A/B/C/D)

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