Skip to Content
Merck

SML0196

Resiquimod

≥98% (HPLC), powder, TLR7/TLR8 agonist

Synonym(s):

4-Amino-2-(ethoxymethyl)-alpha, R-848, R848, S28463, alpha-dimethyl-1H-imidazo(4,5-c)quinoline-1-ethanol

Sign In to View Organizational & Contract Pricing.

Select a Size

All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C17H22N4O2
CAS Number:
144875-48-9
Molecular Weight:
314.38
UNSPSC Code:
51111800
PubChem Substance ID:
329825221
NACRES:
NA.77
MDL number:
MFCD00937759

Product Name

Resiquimod, ≥98% (HPLC)

SMILES string

CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O

InChI

1S/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19)

InChI key

BXNMTOQRYBFHNZ-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white to tan

solubility

DMSO: 10 mg/mL, clear (warmed to 60 °C)

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Related Categories

Application

Resiquimod has been used in the stimulation of bone marrow-derived dendritic cells (BMDCs) stimulation( and B cells. It has also been used as a ligand for toll-like receptors (TLR7) in malignant melanoma cell line B16F10.
Resiquimod may be used in immunological and cancer-related cell signaling studies.

Biochem/physiol Actions

Resiquimod (R-848) is a potent synthetic agonist of TLR7/TLR8 that possesses antiviral and antitumoral activities.
Resiquimod belongs to the class of imidazoquinolinamines compounds with immunomodulatory effects. Resiquimod increases the levels of cytokines such as TNF-α, IL-6 and IFN-α.
Resiquimod is 314.4 Da molecule which elicits immune function during visceral infection with L. infantum Sp. It mediates the trafficking of granulocytes, macrophages, leukocytes and dendritic cells. It is a recommended topical drug for treating skin tumors like actinic keratosis (AK) and superficial basal cell carcinoma.
Resiquimod is an agonist of toll-like receptor 7 and 8 (TLR- and TLR-8).

Features and Benefits

This compound is featured on the Cytokine Receptors (Interleukin-1 Receptor/TIR Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000504648
0000504649
0000504649
0000504648
0000455950

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

AMPK Promotes Xenophagy through Priming of Autophagic Kinases upon Detection of Bacterial Outer Membrane Vesicles
Losier TT, et al.
Cell Reports, 26(8), 2150-2165 (2019)
D H Dockrell et al.
The Journal of antimicrobial chemotherapy, 48(6), 751-755 (2001-12-06)
Augmenting the host's natural immune response to viruses by the administration of exogenous cytokines such as interferon-alpha (IFN-alpha) is a strategy increasingly employed in antiviral therapeutics. Enhancing the release of endogenous cytokines is, however, an alternative approach. The imidazoquinolinamines imiquimod
Anette Christ et al.
Cell, 172(1-2), 162-175 (2018-01-13)
Long-term epigenetic reprogramming of innate immune cells in response to microbes, also termed "trained immunity," causes prolonged altered cellular functionality to protect from secondary infections. Here, we investigated whether sterile triggers of inflammation induce trained immunity and thereby influence innate
Paeonol ameliorates imiquimod-induced psoriasis-like skin lesions in BALB/c mice by inhibiting the maturation and activation of dendritic cells
Meng Y, et al.
International Journal of Molecular Medicine, 39(5), 1101-1110 (2017)
Resiquimod, a topical drug for viral skin lesions and skin cancer
Meyer T, et al.
Expert Opinion on Investigational Drugs, 22(1), 149-159 (2013)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service