Imiquimod-d9 (Synonyms: R 837-d9)

Imiquimod-d₉ is intended for use as an internal standard for the quantification of imiquimod by GC- or LC-MS. Imiquimod is an imidazoquinoline agonist of toll-like receptor 7 (TLR7; EC₅₀ = 2.12 μM).¹ It increases TNF-α and IL-12 p40 production in IFN-γ-treated murine peritoneal macrophages in a concentration- and MyD88-dependent manner.² Topical application of imiquimod (30 μl of 5% cream) increases TNF and IFN levels at the application site in hairless mice.³ Imiquimod dose-dependently increases serum levels of IFN-α in mice when administered by gavage.⁴ It reduces tumor growth in an MC-26 model of murine colon cancer when administered at a dose of 30 mg/kg every three days. Imiquimod (5 mg/kg, intravaginally, twice daily) reduces vaginal viral titer and lesion formation in a guinea pig model of genital HSV-2 infection.⁵ Formulations containing imiquimod have been used in the treatment of actinic keratosis, superficial basal cell carcinoma, and external genital warts.

1.Shukla, N.M., Mallardi, S.S., Mutz, C.A., et al.Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analoguesJ. Med. Chem.53(11)4450-4465(2010) 2.Hemmi, H., Kaisho, T., Takeuchi, O., et al.Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathwayNat. Immunol.3(2)196-200(2002) 3.Imbertson, L.M., Beaurline, J.M., Couture, A.M., et al.Cytokine induction in hairless mouse and rat skin after topical application of the immune response modifiers imiquimod and S-28463J. Invest. Dermatol.110(5)734-739(1998) 4.Sidky, Y.A., Borden, E.C., Weeks, C.E., et al.Inhibition of murine tumor growth by an interferon-inducing imidazoquinolinamineCancer Res.52(13)3528-3533(1992) 5.Harrison, C.J., Jenski, L.J., Voychehovski, T., et al.Modification of immunological responses and clinical disease during topical R-837 treatment of genital HSV-2 infectionAntiviral Res.10(4-5)209-223(1988)