Rimantadine

  • ( RS)- adamantane -1 - ylethylamine (IUPAC)
  • Rimantadinum (Latin )
  • C12H21N ( rimantadine )
  • C12H21N · HCl ( · rimantadine hydrochloride)

J05AC02

Antivirals

  • 373-375 ° C ( rimantadine • hydrochloride racemate)
  • 400-402 ° C ( rimantadine • hydrochloride enantiomers)

640 mg · kg -1 ( LD50, Rat, oral, hydrochloride)

Template: Infobox chemical / molecular formula search available

Rimantadine [trade name: Flumadine ® ( USA) ] is a drug for the treatment and prevention of influenza rarely also of type A and was approved by the FDA in 1993.

The Centers for Disease Control and Prevention recommended in January 2006, rimantadine and oseltamivir no longer prescribe the influenza type H3N2, after an increase in resistance of 2 % in 2004 was observed over 11 % in 2005 to 91%.

Is a derivative of adamantane.

Synthesis

The synthesis of racemic rimantadine proceeds from the 1- adamantoyl, where in the first step with diethyl malonate and magnesium 1- Acetyladamantan is formed. This can be implemented via the oxime, followed by reduction with lithium aluminum hydride or directly by a reductive amination in the presence of cobalt catalysts for the target compound.

The resolution can be carried out with enantiomerically pure Tartranil.

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System DrugBank Journal of Medicinal Chemistry Digital Object Identifier
684003
de