An internal standard for the quantification of imiquimod
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Unlabeled Version(s)
14956Imiquimod
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Imiquimod-d9

Item No. 26424

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2-(methyl-d3)propyl-1,1,2,3,3,3-d6)-1H-imidazo[4,5-c]quinolin-4-amine
CAS Number
2712126-48-0
Molecular Formula
C14H7D9N4
Formula Weight
249.4
Purity
≥99% deuterated forms (d1-d9)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/ml
SMILES
NC1=NC2=C(C3=C1N=CN3C([2H])([2H])C(C([2H])([2H])[2H])([2H])C([2H])([2H])[2H])C=CC=C2
InChi Code
InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)/i1D3,2D3,7D2,9D
InChi Key
DOUYETYNHWVLEO-UEZIPFSLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $267

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    1 mg

    $505

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    Cayman Chemical
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    Product Description

    Imiquimod-d9 is intended for use as an internal standard for the quantification of imiquimod (Item No. 14956) 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shukla, N.M., Mallardi, S.S., Mutz, C.A., et al. Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues. J. 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 pathway. Nat. 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-28463. J. 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 imidazoquinolinamine. Cancer 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 infection. Antiviral Res. 10(4-5), 209-223 (1988).