4922. Imiquimod

Nomenclature

CAS number: 99011-02-6
1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine; 4-amino-1-isobutyl-1H-imidazo[4,5-c]quinoline; R-837; S-26308; Aldara (3M Pharma).
C14H16N4; mol wt 240.30.
C 69.97%, H 6.71%, N 23.32%.

Description and references

Immune response modifier; stimulates production of interferon-α, q.v. Prepn: J. F. Gerster, EP 145340; idem, US 4689338 (1985, 1987 both to Riker). Mechanism of action study: K. Megyeri et al., Mol. Cell. Biol. 15, 2207 (1995). Clinical pharmacology: P. L. Witt et al., Cancer Res. 53, 5176 (1993). Clinical trial for genital warts: L. Edwards et al., Arch. Dermatol. 134, 25 (1998). Series of articles on pharmacology and clinical experience in cutaneous viral infections: J. Am. Acad. Dermatol. 43, S1-S30 (2000).

Chemical structure

Properties

Crystals from DMF, mp 292-294°.

Therapeutic Category

Antiviral; immunomodulator.

Keywords

Immunomodulator; Antiviral; Imidazoquinolines