8224. Rimantadine

Nomenclature

CAS number: 13392-28-4
α-Methyltricyclo[3.3.1.13,7]decane-1-methanamine; α-methyl-1-adamantanemethylamine; remantadin(e).
C12H21N; mol wt 179.30.
C 80.38%, H 11.81%, N 7.81%.

Description and references

Deriv of adamantane, q.v. Prepn: NL 6408505; W. W. Prichard, US 3352912 (1965, 1967 both to du Pont). Antiviral activity: A. Tsunoda et al., Antimicrob. Agents Chemother. 1965, 553. Effects on influenza in mice: J. W. McGahen et al., Ann. N.Y. Acad. Sci. 173, 557 (1970). Mechanism of action study: A. Bukrinskaya et al., Arch. Virol. 66, 275 (1980); eidem, J. Gen. Virol. 60, 49 (1982). Pharmacokinetics in humans: R. J. Wills et al., Antimicrob. Agents Chemother. 31, 826 (1987). Clinical trial in prophylaxis of influenza A infection: R. Dolin et al., N. Engl. J. Med. 307, 580 (1982). Comparative toxicity of rimantadine and amantadine in healthy adults: F. G. Hayden et al., Antimicrob. Agents Chemother. 19, 226 (1981). Controlled study of CNS effects: V. M. Millet et al., ibid. 21, 1 (1982). Review of studies in the USSR on exptl and clinical pharmacology: D. M. Zlydnikov et al., Rev. Infect. Dis. 3, 408-421 (1981).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 1501-84-4
EXP-126; Flumadine (Roche); Meradan(e) (USSR); Roflual (Roche).
C12H21N.HCl; mol wt 215.76.
C 66.80%, H 10.28%, N 6.49%, Cl 16.43%.

Properties

White crystals, mp 373-375° (sealed tube).

Therapeutic Category

Antiviral.

Keywords

Antiviral; Adamantanes