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rimantadine
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. 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.〔(Antiviral Agents for the Treatment and Chemoprophylaxis of Influenza: Recommendations of the Advisory Committee on Immunization Practices (ACIP) )〕
== History ==
Rimantadine was discovered in 1963〔(US patent 3352912 to W. W. Prichard )〕〔(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.''〕 and patented in 1965 in the USA by William W. Prichard in Du Pont & Co., Wilmington, Delaware (patent on new chemical compound , 1965 and on the first method of synthesis , 1967).〔(United States Patent № 4551552: Process for preparing rimantadine )〕〔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.〕 Prichard's methods of synthesis of rimantadine from the corresponding ketone oxime were based on its reduction with lithium aluminum hydride.
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