Imiquimod [99011-02-6]

Cat# HY-B0180-200mg

Size : 200mg

Brand : MedChemExpress

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Imiquimod (R 837), an immune response modifier, is a selective toll like receptor 7 (TLR7) agonist. Imiquimod exhibits antiviral and antitumor effects in vivo. Imiquimod can be used for the research of external genital, perianal warts, cancer and COVID-19.

For research use only. We do not sell to patients.

Imiquimod Chemical Structure

Imiquimod Chemical Structure

CAS No. : 99011-02-6

This product is a controlled substance and not for sale in your territory.

Based on 39 publication(s) in Google Scholar

Other Forms of Imiquimod:

  • Imiquimod-d6 Get quote
  • Imiquimod-d9 Get quote
  • Imiquimod hydrochloride Get quote
  • Imiquimod maleate Get quote
  • Imiquimod dihydrochloride Get quote
  • Imiquimod (Standard) Get quote

    Imiquimod purchased from MedChemExpress. Usage Cited in: Nat Commun. 2016 May 25;7:11724.  [Abstract]

    Freshly prepared splenic B cells are left unstimulated (lanes 1 and 4), or stimulated by 10 μg/mL αIgM for 6 or 24 h (lanes 2 and 3), or by 1 μg/mL IMQ for 6, 24, 48 and 72 h (lanes 5-8), or by αIgM and IMQ for 24 or 48 h (lanes 9+10), respectively.

    View All Toll-like Receptor (TLR) Isoform Specific Products:

    View All Isoforms
    TLR3 TLR8 TLR9 TLR2 TLR4 TLR7 TLR1 TLR6

    View All HSV Isoform Specific Products:

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    HSV-1 HSV-2 HSV
    Description

    Imiquimod (R 837), an immune response modifier, is a selective toll like receptor 7 (TLR7) agonist. Imiquimod exhibits antiviral and antitumor effects in vivo. Imiquimod can be used for the research of external genital, perianal warts, cancer and COVID-19[1][2].

    IC50 & Target[1][3]

    TLR7

     

    HSV-1

     

    Cellular Effect
    Cell Line Type Value Description References
    A-375 IC50
    70.3 μM
    Compound: Imiquimod
    Cytotoxicity against human A375 cells after 96 hrs by MTT assay
    Cytotoxicity against human A375 cells after 96 hrs by MTT assay
    [PMID: 19278757]
    A-375 IC50
    70.3 μM
    Compound: imiquimod
    Cytotoxicity against human A375 cells after 96 hrs by MTT assay
    Cytotoxicity against human A375 cells after 96 hrs by MTT assay
    [PMID: 18513976]
    HEK293 EC50
    > 270 μM
    Compound: 1
    Agonist activity at human TLR8 transfected in HEK cells assessed as NFkappaB induction after 24 hrs by specific secreted alkaline phosphatase gene assay
    Agonist activity at human TLR8 transfected in HEK cells assessed as NFkappaB induction after 24 hrs by specific secreted alkaline phosphatase gene assay
    [PMID: 22837811]
    HEK293 EC50
    10.7 μM
    Compound: 1
    Agonist activity at human TLR-7 expressed in HEK293 cells after 24 hrs by SEAP reporter gene assay
    Agonist activity at human TLR-7 expressed in HEK293 cells after 24 hrs by SEAP reporter gene assay
    [PMID: 24383475]
    HEK293 EC50
    12.1 μM
    Compound: 1
    Agonist activity at human TLR7 transfected in HEK cells assessed as NFkappaB induction after 24 hrs by specific secreted alkaline phosphatase gene assay
    Agonist activity at human TLR7 transfected in HEK cells assessed as NFkappaB induction after 24 hrs by specific secreted alkaline phosphatase gene assay
    [PMID: 22837811]
    HEK293 EC50
    2.12 μM
    Compound: 1
    Agonist activity at human TLR7 expressed in NF-kappaB-stimulated HEK293 cells assessed as induction of secreted alkaline phosphatase expression by reporter gene assay
    Agonist activity at human TLR7 expressed in NF-kappaB-stimulated HEK293 cells assessed as induction of secreted alkaline phosphatase expression by reporter gene assay
    [PMID: 20481492]
    HEK293 EC50
    6.2 μM
    Compound: 1
    Agonist activity at human TLR7 in HEK293 cells cotransfected with SEAP reporter gene assessed as activity of SEAP incubated for 24 hrs by quanti-blue staining based SEAP reporter gene assay
    Agonist activity at human TLR7 in HEK293 cells cotransfected with SEAP reporter gene assessed as activity of SEAP incubated for 24 hrs by quanti-blue staining based SEAP reporter gene assay
    [PMID: 31247373]
    LS174T IC50
    34.4 μM
    Compound: imiquimod
    Cytotoxicity against human LS174T cells after 96 hrs by MTT assay
    Cytotoxicity against human LS174T cells after 96 hrs by MTT assay
    [PMID: 18513976]
    MCF7 IC50
    145 μM
    Compound: imiquimod
    Cytotoxicity against human MCF7 cells after 96 hrs by MTT assay
    Cytotoxicity against human MCF7 cells after 96 hrs by MTT assay
    [PMID: 18513976]
    Raji IC50
    139 μM
    Compound: imiquimod
    Cytotoxicity against human Raji cells after 96 hrs by MTT assay
    Cytotoxicity against human Raji cells after 96 hrs by MTT assay
    [PMID: 18513976]
    In Vivo

    Imiquimod (IMQ) can be used to induce psoriasis models[5].

    Induction of psoriasis Model[5]
    Background
    Lmiquimod (IMQ) induces inflamed scaly skin lesions resembling plaque-type psoriasis. IMQ induces epidermal expression of IL-23, IL-17A, and IL-17F, as well as an increase in splenic Th17 cells.
    Specific Mmodeling Methods
    Mice: BALB/c • male • 8-week-old
    Administration: 3.125 mg/day • skin • 6 days
    Note
    IMQ cream preparation [7]:
    (1) Prepare BM of lipids
    STA and OA were melted at 75 °C followed by the addition of IMQ (3.5% of the BM, w/w) under continuous stirring.
    Polysorbate 80 and stearoyl polyoxyl-32 glycerides at a 50:50 ratio were dispersed in water heated separately to 75 °C and added to the BM phase under continuous stirring.
    (2) Prepare nanostructured lipid carriers (NLCs)
    The mixture was then subjected to high-shear homogenization followed by ultrasonication.
    The mixture was then rapidly cooled in an ice bath to allow the formation of NLCs.
    Modeling Indicators
    Behavior Observation: Induced the back skin of the mice started to display signs of erythema, scaling, and thickening.
    Resulted in hyperproliferative keratinocytes and a disturbed epidermal differentiation (parakeratosis).
    Correlated Product(s): /
    Opposite Product(s): /

    MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

    Animal Model: BALB/c mice (8-11 week) [5]
    Dosage: 3.125 mg/day, 6 day
    Administration: skin
    Result: Induced the back skin of the mice started to display signs of erythema, scaling, and thickening.
    Resulted in hyperproliferative keratinocytes and a disturbed epidermal differentiation (parakeratosis).
    Clinical Trial
    Molecular Weight

    240.30

    Formula

    C14H16N4

    CAS No.

    99011-02-6

    Appearance

    Solid

    Color

    White to off-white

    SMILES

    NC1=NC2=CC=CC=C2C3=C1N=CN3CC(C)C

    Shipping

    Room temperature in continental US; may vary elsewhere.

    Storage
    Powder -20°C 3 years
    4°C 2 years
    In solvent -80°C 2 years
    -20°C 1 year
    Solvent & Solubility
    In Vitro: 

    DMSO : 3.28 mg/mL (13.65 mM; ultrasonic and warming and adjust pH to 7 with 1 M HCL and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

    H2O : 2.64 mg/mL (10.99 mM; ultrasonic and adjust pH to 2 with HCl)

    Methanol : < 1 mg/mL (insoluble)

    Preparing
    Stock Solutions
    Concentration Solvent Mass 1 mg 5 mg 10 mg
    1 mM 4.1615 mL 20.8073 mL 41.6146 mL
    5 mM 0.8323 mL 4.1615 mL 8.3229 mL
    View the Complete Stock Solution Preparation Table

    * Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
    Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

    * Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

    • Molarity Calculator

    • Dilution Calculator

    Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

    Mass
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    Molecular Weight *

    Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

    This equation is commonly abbreviated as: C1V1 = C2V2

    Concentration (start)

    C1

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    Volume (start)

    V1

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    Concentration (final)

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    In Vivo Dissolution Calculator
    Please enter the basic information of animal experiments:

    Dosage

    mg/kg

    Animal weight
    (per animal)

    g

    Dosing volume
    (per animal)

    μL

    Number of animals

    Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
    Calculation results:
    Working solution concentration: mg/mL
    Purity & Documentation

    Purity: 99.96%

    References
    • [1]. Athina Angelopoulou, et al. Imiquimod - A toll like receptor 7 agonist - Is an ideal option for management of COVID 19. Environ Res. 2020 Sep; 188: 109858.  [Content Brief]

      [2]. Aditya K Gupta, et al. Imiquimod: a review. J Cutan Med Surg. Nov-Dec 2002;6(6):554-60.  [Content Brief]

      [3]. Yuji Kan, et al. Imiquimod suppresses propagation of herpes simplex virus 1 by upregulation of cystatin A via the adenosine receptor A1 pathway. J Virol. 2012 Oct;86(19):10338-46.  [Content Brief]

      [4]. Michael P Schön, et al. The small antitumoral immune response modifier imiquimod interacts with adenosine receptor signaling in a TLR7- and TLR8-independent fashion. J Invest Dermatol. 2006 Jun;126(6):1338-47.  [Content Brief]

      [5]. Leslie van der Fits, et al. Imiquimod-induced psoriasis-like skin inflammation in mice is mediated via the IL-23/IL-17 axis. J Immunol. 2009, 182, 9.  [Content Brief]

      [6]. Ajla Smajlović, et al. Molecular and histopathological profiling of imiquimod induced dermatosis in Swiss Wistar rats: contribution to the rat model for novel anti-psoriasis treatments. Mol Biol Rep. 2021, 48, 5.  [Content Brief]

      [7]. Sangseo Kim, et al. Development and Optimization of Imiquimod-Loaded Nanostructured Lipid Carriers Using a Hybrid Design of Experiments Approach. Int J Nanomedicine. 2023.  [Content Brief]

    Complete Stock Solution Preparation Table

    * Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
    Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

    Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
    H2O / DMSO 1 mM 4.1615 mL 20.8073 mL 41.6146 mL 104.0366 mL
    5 mM 0.8323 mL 4.1615 mL 8.3229 mL 20.8073 mL
    10 mM 0.4161 mL 2.0807 mL 4.1615 mL 10.4037 mL

    * Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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    Imiquimod Related Classifications

    Help & FAQs

    Keywords:

    Imiquimod99011-02-6R 837R837R-837Toll-like Receptor (TLR)AutophagySARS-CoVHSVSARS coronavirusHerpes simplex virushumanpapillomaviruswartsmolluscumcontagiosumactinickeratosisbasal ,cellcarcinomasquamouscellBowen'sdiseasenongenitalinfectionvulvarintraepithelialneoplasiaInhibitorinhibitorinhibit

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