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Rimantadine



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 antiviral drug 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 was approved by the Food and Drug Administration (FDA) in 1994.

Additional recommended knowledge

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.[citations needed]

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.

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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Rimantadine". A list of authors is available in Wikipedia.
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