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SML0196

Resiquimod

Name: Resiquimod
Brand: SIGMA

≥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

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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

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated, protect from light

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Product Name

Resiquimod, ≥98% (HPLC)

Quality Level

100

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

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

Related Categories

Bioactive Small Molecule Agonists

Bioactive Small Molecules

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 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 (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 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

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Certificates of Analysis (COA)

Lot/Batch Number

0000535887

0000504648

0000504649

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Suppression of innate and adaptive B cell activation pathways by antibody coengagement of FcgammaRIIb and CD19

Szili,D, et al.

MAbs, 6(4), 991-999 (2014)

A pilot clinical trial testing topical resiquimod and a xenopeptide as immune adjuvants for a melanoma vaccine targeting MART-1.

Matthew S Block et al.

Melanoma research, 29(4), 420-427 (2018-12-07)

A vaccine that could expand melanoma-specific T cells might reduce the risk of recurrence of resected melanoma and could provide an alternative or adjunct to standard immunotherapy options. We tested the safety and immunogenicity of a vaccine coupling a melanoma-associated

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)

Imiquimod and resiquimod as novel immunomodulators.

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

Western Diet Triggers NLRP3-Dependent Innate Immune Reprogramming.

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

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Articles

Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Global Trade Item Number

SKU	GTIN
SML0196-10MG	04061837077050
SML0196-50MG	04061837077067

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