Rimantadine hydrochloride

Description

Rimantadine hydrochloride is an antiviral analogue of amantadine, reportedly useful in the prophylaxis and treatment of influenza A. Compared with amantadine, nmantadine appears to have a lower side-effect profile.

Chemical Properties

White Crystalline Solid

Originator

DuPont (USA)

Uses

Rimantadine Hydrochloride is used as an antiviral agent.

Definition

ChEBI: Rimantadine hydrochloride is an organic molecular entity.

brand name

Flumadine (Forest);Roflual.

Synthesis

Example 3: To a Parr hydrogenation flask was added 13.7 g of 1-adamantyl methyl ketoxime (CAS: 78679-71-7), 4.0 g of 5% Pt/C catalyst and 200 ml of glacial acetic acid. After displacing the air in the flask with hydrogen, the hydrogenation reaction was carried out at 30-35 psia (200-240 KPa) hydrogen pressure for 2.25 h at room temperature. After the hydrogen absorption ceased, the reaction mixture was left to stand overnight. Subsequently, the catalyst was filtered off and the acetic acid solution was concentrated to about one-third of the original volume by distillation under reduced pressure. To the concentrated solution, 150 ml of water was added and the pH was adjusted to alkaline with sodium hydroxide solution to obtain an emulsion mixture. The emulsion was extracted twice with 100 ml of dichloromethane. The organic phases were combined, dried with magnesium sulfate and filtered. Hydrogen chloride gas was passed into the clarified dichloromethane solution and a white solid was precipitated. Next, 100 ml of ethyl acetate was added to induce the precipitation of more solids. The solid was collected by filtration to give 11.4 g of amantadine hydrochloride in 75% yield.

References

[1] koff w c, elm jr j l, halstead s b. suppression of dengue virus replication in vitro by rimantadine hydrochloride[j]. the american journal of tropical medicine and hygiene, 1981, 30(1): 184-189.
[2] koff w c, peavy d l, knight v. inhibition of in vitro proliferative responses of human lymphocytes by rimantadine hydrochloride[j]. infection and immunity, 1979, 23(3): 665-669.
[3] hayden f g, monto a s. oral rimantadine hydrochloride therapy of influenza a virus h3n2 subtype infection in adults[j]. antimicrobial agents and chemotherapy, 1986, 29(2): 339-341.