Rimantadine

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1 : 1 mixture (racemate)
Systematic (IUPAC) name
(RS)-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
SMILES eMolecules & PubChem
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
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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.

Contents

[edit] 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.[2]

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.

[edit] 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%.[3] Cimetidine also affects the body's uptake of rimantadine.

[edit] Possible Side effects

Rimantadine can produce gastrointestinal and central nervous system adverse effects. Approximately 6% of patients (compared to 6% of patients taking a placebo) reported side effects.[4] Common side effects include:

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

[edit] 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. PMID 15561867. PMC 529183. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=15561867. 
  2. ^ 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. PMID 18669647. 
  3. ^ "fda.gov". http://www.fda.gov/cder/drug/antivirals/influenza/flumadine.htm. Retrieved 2008-11-05. 
  4. ^ "CDC - Influenza (Flu)". http://www.cdc.gov/flu/professionals/treatment/side-effects.htm. Retrieved 2008-11-05. 

[edit] External links

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