[CAS NO. 144875-48-9] Resiquimod

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PRODUCTS SPECIFICATIONS [144875-48-9]

Catalog

HY-13740

Brand

MCE

CAS

144875-48-9

DESCRIPTION [144875-48-9]

Overview

MDL	MFCD00937759
Molecular Weight	314.38
Molecular Formula	C17H22N4O2
SMILES	OC(C)(C)CN1C(COCC)=NC2=C1C3=CC=CC=C3N=C2N

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

35 Publications Citing Use of MCE

Summary

Resiquimod is a Toll-like receptor 7 and 8 ( TLR7/TLR8 ) agonist that induces the upregulation of cytokines such as TNF-α, IL-6 and IFN-α.

IC50 & Target

TLR7

TLR8

In Vitro

Resiquimod (R-848) induces both hapten- and allergen-specific circulating T cells, including TH2 effectors, to produce IFN-γ and even to lose the ability to produce IL-4 ^[2] . Resiquimod (R848) enhances PBL proliferation in a dose-dependent manner, and increases the number of BrdU-positive cells in BrdU incorporation assay. Cells treated with R848 exhibits significantly increased (3.5-fold) luciferase (a reporter of NF-κB activity) activity ^[3] .

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

In Vivo

Resiquimod (R-848) (50 μg/bird, i.m. route) significantly up-regulates the expression of IFN-α, IFN-β, IFN-γ, IL-1β, IL-4, iNOS and MHC-II genes in SPF chicken ^[1] .

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

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT00175435	University of British Columbia	Hepatitis B	August 2005	Phase 1\|Phase 2
NCT00948961	Celldex Therapeutics	Advanced Malignancies	September 2009	Phase 1\|Phase 2
NCT01808950	Spirig Pharma Ltd.	Nodular Basal Cell Carcinoma	February 2013	Phase 1\|Phase 2
NCT02126579	Craig L Slingluff, Jr\|University of Virginia	Melanoma\|Metastatic Melanoma\|Mucosal Melanoma	May 1, 2014	Phase 1\|Phase 2
NCT00960752	M.D. Anderson Cancer Center	Melanoma	May 20, 2010	Phase 2
NCT00116662	Graceway Pharmaceuticals, LLC	Warts	March 2005	Phase 2
NCT00114920	Graceway Pharmaceuticals, LLC	Warts	March 2004	Phase 2
NCT01737580	University of British Columbia	Influenza Vaccination in Seniors	April 2013	Phase 1
NCT00821652	Nina Bhardwaj\|Cancer Research Institute, New York City\|Icahn School of Medicine at Mount Sinai	Tumors	February 2009	Phase 1
NCT02090374	Imperial College London	Allergic Rhinitis\|Asthma\|Latent Tuberculosis	March 2014	Not Applicable
NCT01748747	Mayo Clinic\|National Cancer Institute (NCI)	Recurrent Melanoma\|Stage IIA Melanoma\|Stage IIB Melanoma\|Stage IIC Melanoma\|Stage IIIA Melanoma\|Stage IIIB Melanoma\|Stage IIIC Melanoma\|Stage IV Melanoma	October 2012	Early Phase 1
NCT00470379	Mayo Clinic\|National Cancer Institute (NCI)	Melanoma (Skin)	April 2006	Early Phase 1
NCT00115141	Graceway Pharmaceuticals, LLC	Warts	April 2004	Phase 2
NCT00117923	Graceway Pharmaceuticals, LLC	Warts	August 2004	Phase 2
NCT01204684	Jonsson Comprehensive Cancer Center	Glioma\|Anaplastic Astrocytoma\|Anaplastic Astro-oligodendroglioma\|Glioblastoma	October 8, 2010	Phase 2
NCT00116675	Graceway Pharmaceuticals, LLC	Warts	March 2005	Phase 2
NCT01583816	Spirig Pharma Ltd.	Actinic Keratosis	May 2012	Phase 2
NCT01676831	Abramson Cancer Center of the University of Pennsylvania	Cutaneous T Cell Lymphoma	February 2012	Phase 1\|Phase 2
NCT00117871	Graceway Pharmaceuticals, LLC	Warts	October 2004	Phase 2

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMF : 50 mg/mL ( 159.04 mM ; Need ultrasonic)

DMSO : ≥ 30 mg/mL ( 95.43 mM )

Methanol : 25 mg/mL ( 79.52 mM ; Need ultrasonic)

H ₂ O : 0.1 mg/mL ( 0.32 mM ; Need ultrasonic)

* "≥" means soluble, but saturation unknown.

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	3.1809 mL	15.9043 mL	31.8086 mL
5 mM	0.6362 mL	3.1809 mL	6.3617 mL
10 mM	0.3181 mL	1.5904 mL	3.1809 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 5% DMSO >> 40% PEG300 >> 5% Tween-80 >> 50% saline

Solubility: ≥ 2.5 mg/mL (7.95 mM); Clear solution
2.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 2.08 mg/mL (6.62 mM); Clear solution
3.

Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

Solubility: ≥ 2.08 mg/mL (6.62 mM); Clear solution
4.

Add each solvent one by one: 10% DMSO >> 90% corn oil

Solubility: ≥ 2.08 mg/mL (6.62 mM); Clear solution

* All of the co-solvents are available by MCE.

References

Synonyms

1H-Imidazo[4,5-c]quinoline-1-ethanol, 4-amino-2-(ethoxymethyl)-α,α-dimethyl-

4-Amino-2-(ethoxymethyl)-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

S 28463

R 848

Resiquimod

1-[4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

Resimiquimod

4-Amino-2-(ethoxymethyl)-1-(2-hydroxyisobutyl)imidazo[4,5-c]quinoline

1-[4-Amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol