HY-B0180-100mg | Imiquimod [99011-02-6] Clinisciences

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
10 mM	0.4161 mL	2.0807 mL	4.1615 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)

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

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

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%

Select Batch:

SDS (419 KB)

COA (256 KB) LCMS (120 KB)

Handling Instructions (2659 KB)

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

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.

Imiquimod Related Classifications

Inflammation/Immunology Infection Cancer
Cancer Targeted Therapy Cancer Immunotherapy Cancer Metabolism and Metastasis

Immunology/Inflammation Autophagy Anti-infection
Toll-like Receptor (TLR) Autophagy SARS-CoV HSV

Imiquimod [99011-02-6]

Cat# HY-B0180-100mg

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Complete Stock Solution Preparation Table

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