8151. Resiquimod

Nomenclature

CAS number: 144875-48-9
4-Amino-2-(ethoxymethyl)-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol; R-848; S-28463.
C17H22N4O2; mol wt 314.38.
C 64.95%, H 7.05%, N 17.82%, O 10.18%.

Description and references

Immune response modulator structurally similar to imiquimod, q.v. Induces cytokine secretion by monocytes and activates antibody secretion by B cells. Prepn: J. F. Gerster et al., WO 9215582; eidem, US 5389640 (1992, 1995 both to 3M). Immunomodulating and antiviral activities: M. A. Tomai et al., Antiviral Res. 28, 253 (1995). Mechanism of action study: G. A. Bishop et al., Cell. Immunol. 208, 9 (2001). Clinical evaluation in genital herpes: S. L. Spruance et al., J. Infect. Dis. 184, 196 (2001). Review of development: J. J. Wu et al., Antiviral Res. 64, 79-83 (2004).

Chemical structure

Properties

Colorless, crystalline solid, mp 190-193°.

Therapeutic Category

Antiviral.

Keywords

Antiviral; Imidazoquinolines; Immunomodulator