Rimantadine hydrochloride

Amantadine hydrochloride [665-66-7] (1-adamantanamine hydrochloride, 41), C qH N HQ., (93) is a good example of a narrow-spectmm agent active only against influenza A vims. It became the first antiviral dmg available for systemic use in the United States when it was approved by the FDA in 1966 for use against Asian influenza. In 1976, FDA approval was extended to the use of amantadine for the reHef of symptoms of all influenza A strains. Amantadine is marketed by Du Pont de Nemours Co., Inc. A stmcturaHy related dmg, rimantadine hydrochloride [1501 -84-4] C 2H2 N HQ, (a-methyl-l-adamantanemethylamine hydrochloride, 42), is widely used in Russia to treat influenza A vims (94). 

Amantadine hydrochloride Rimantadine hydrochloride Figure 7.17 Examples of host cell penetration inhibitors... 

Chemical Name 1-Adamantanemethylamine, a-methyl-, hydrochloride Common Name Remantadine hydrochloride Rimantadine hydrochloride Structural Formula ... 

Bukrinskaya AG, Vorkunova NK, Narmanbetova RA. Rimantadine hydrochloride blocks the second step of influenza virus uncoating. Arch Virol 1980 66(3) 275-82. 

Rimantadine hydrochloride, an alpha-methyl derivative of amantadine (alpha-methyl-l-adamantane methylamine hydrochloride), is more active than amantadine against influenza A viruses in vitro and in laboratory animals. It is an alternative to amantadine for the prevention and treatment of influenza A virus infections in adults and for the prevention of influenza in children. Adverse effects have been considered to be less common with rimantadine (SEDA-8, 143), and it is generally tolerated better than amantadine, because it causes fewer nervous system adverse effects (1). Unfortunately, rimantadine is more costly, which has led many institutions to develop influenza treatment guidelines. Both drugs work by blocking the M2 ion channel, which is needed to affect a pH change that helps to initiate viral uncoating. 

Rimantadine hydrochloride (a-methyl-1-adamantanemethylamine hydrochloride) is a synthetic adamatane derivative that is structurally and pharmacologically related to amantadine (21,22). It appears to be more effective than amantadine hydrochloride against influenza A, with fewer CNS side effects. Rimantadine hydrochloride is thought to interfere with virus uncoating by inhibiting the release of specific proteins. It may act by inhibiting RT or the synthesis of virus-specific RNA, but it does not inhibit virus adsorption or penetration. It appears to produce a virustatic effect early in the virus replication. It is used widely in Russia and Europe. 

Burlington DB, Meiklejohn G, Mostow SR. Anti-influenza A virus activity of amantadine hydrochloride and rimantadine hydrochloride in ferret tracheal ciliated epithelium. Antimicrob Agents Chemother 1982 21 794-799. 

Flumadine (Rimantadine hydrochloride). Forest Pharmaceuticals, Inc. US Prescribing information, June 2006. 

Tominack RL, Hayden EG. Rimantadine hydrochloride and amantadine hydrochloride use in influenza A virus infections. Infect Dis Clin North Am 1987 1 459-478. 

---