Rimantadine

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Rimantadine
Systematic (IUPAC) name
1-(1-adamantyl)ethanamine
Identifiers
CAS number	13392-28-4
ATC code	J05AC02
PubChem	5071
DrugBank	APRD01219
Chemical data
Formula	C₁₂H₂₁N
Mol. mass	179.302 g/mol
Pharmacokinetic data
Bioavailability	well absorbed
Protein binding	40%
Metabolism	Hepatic hydroxylation and glucuronidation
Half life	25.4 ± 6.3 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C (U.S.)
Legal status	℞-only (U.S.)
Routes	Oral

Rimantadine (INN, sold under the trade name Flumadine®) is an orally administered medicine 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. It is a derivate of adamantane, like a similar drug amantadine. It Drug Administration]] (FDA) in 1994.

1 Mechanics
2 Drug interactions
3 Adverse effects
4 External links

[edit] Mechanics

Scientists do not understand why rimantadine works, but believe it inhibits 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.

[edit] Drug interactions

Taking acetaminophen (Tylenol) or aspirin while taking rimantadine is known to reduce the body's uptake of rimantadine by approximately 12%.[1] Cimetidine also affects the body's uptake of rimantadine.

[edit] Adverse effects

Rimantadine can produce gastrointestinal and central nervous system adverse effects. Studies have shown it produces fewer side effects than other anti-viral influenza treatments. Approximately 6% of patients (compared to 6% of patients taking a placebo) reported side effects.[2] Common side effects include:

nausea
upset stomach
nervouseness
tiredness
lightheadedness
trouble sleeping
difficulty concentrating

[edit] External links

v • d • e Antivirals (primarily J05A, also S01AD and D06BB)
Anti-herpesvirus	Aciclovir, Cidofovir, Docosanol, Famciclovir, Fomivirsen, Foscarnet, Ganciclovir, Idoxuridine, Penciclovir, Trifluridine, Tromantadine, Valaciclovir, Valganciclovir, Vidarabine
Anti-influenza agents	Amantadine, Arbidol, Oseltamivir, Peramivir, Rimantadine, Zanamivir
Antiretrovirals: NRTIs	Abacavir, Didanosine, Emtricitabine, Lamivudine, Stavudine, Zalcitabine, Zidovudine
Antiretrovirals: NtRTIs	Tenofovir
Antiretrovirals: NNRTIs	Efavirenz, Delavirdine, Nevirapine, Loviride
Antiretrovirals: PIs	Amprenavir, Atazanavir, Darunavir, Fosamprenavir, Indinavir, Lopinavir, Nelfinavir, Ritonavir, Saquinavir, Tipranavir
Antiretrovirals: Fusion inhibitors	Enfuvirtide
Other antiviral agents	Adefovir, Fomivirsen, Imiquimod, Inosine, Interferon, Podophyllotoxin, Ribavirin, Viramidine