144875-48-9

Basic information

• Product Name: RESIQUIMOD
• Synonyms: RESIQUIMOD;1-[4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-C]quinolin-1-yl]-2-methylpropan-2-ol;Chebi:36706;4-Amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol;4-Amino-2-(ethoxymethyl)-alpha;alpha-dimethyl-1H-imidazo(4,5-c)quinoline-1-ethanol;resquimod;R848,Resiquimod
• CAS NO: 144875-48-9
• Molecular Formula: C₁₇H₂₂N₄O₂
• Molecular Weight: 314.387
• Product Categories: Agonist;Anti-virals;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 144875-48-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 190-193°
• Boiling Point: 553.6°Cat760mmHg
• Flash Point: 288.6°C
• Appearance: white to tan/
• Density: 1.28
• Vapor Pressure: 4.33E-13mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble10mg/mL, clear (warmed to 60 °C)
• PKA: 14.63±0.29(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
• Merck: 14,8151
• CAS DataBase Reference: RESIQUIMOD(CAS DataBase Reference)
• NIST Chemistry Reference: RESIQUIMOD(144875-48-9)
• EPA Substance Registry System: RESIQUIMOD(144875-48-9)

Safety Data

• WGK Germany: 3
• RTECS: NJ5911320
• Hazardous Substances Data: 144875-48-9(Hazardous Substances Data)

Usage

Description

Resiquimod (CAS 144875-48-9) is a Toll-like receptor 7/8 agonist.1 May be used as an immune adjuvant in cancer vaccines.2 Resiquimod-carrying synthetic vaccine particles augment the immune response to encapsulated antigen and exhibit strong local immune activation without inducing systemic cytokine release.3 Topical treatment of wild-type mice induces systemic autoimmune disease which may be used as a model of systemic Lupus erythematosus.4? It displayed potent antiviral activity (EC50 = 23.5 nM) in a murine norovirus replicon model.5

Uses

Different sources of media describe the Uses of 144875-48-9 differently. You can refer to the following data:
1. Resiquimod is an imidazoquinoline derivative that acts as an immune response modifier. Resiquimod shows antitumor and antiviral activity and is used in the treatment of skin lesions such as herpes simplex virus. Resiquimod is a toll-like receptor 9 (TLR7) agonist.
2. 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.

Biochem/physiol Actions

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.

References

1) Jurk et al. (2002), Human TLR7 or TLR8 independently confer responsiveness to the antiviral compound R-848; Nat. Immunol., 3 499 2) Sabado et al. (2015), Resiquimod as an immunologic adjuvant for NY-ESO-1 protein vaccination in patients with high-risk melanoma; Cancer Immunol. Res., 3 278 3) Ilyinskii et al. (2014), Adjuvant-carrying synthetic vaccine particles augment the immune response to encapsulated antigen and exhibit strong local immune activation without inducing systemic cytokine release; Vaccine, 32 2882 4) Yokogawa et al. (2014), Epicutaneous application of toll-like receptor 7 agonists leads to systemic autoimmunity in wild-type mice: a new model of systemic Lupus erthematosus; Arthritis Rheumatol., 66 694 5) Tuipulotu et al. (2018), TLR7 Agonists Display Potent Antiviral Effects against Norovirus Infection via Innate Stimulation; Antimicrob. Agents Chemother., 62 e02417

InChI:InChI=1/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)

Upstream product

• 144875-99-0 α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol 
• 7440-44-0 pyrographite 
• 144876-01-7 4-chloro-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol 
• 132521-66-5 2,4-dichloro-3-nitroquinoline 
• 70254-44-3 2,4-dihydroxyquinoline 
• 15151-57-2 2,4-dihydroxy-3-nitroquinoline 
• 253120-65-9 N-{2-chloro-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-ethoxyacetamide 
• 133860-78-3 1-[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol 
• 133860-77-2 1-[(2-chloro-3-nitro-4-quinolinyl)amino]-2-methyl-2-propanol 

Downstream Products

• 102-76-1 triacetylglycerol 

Relevant articles and documents

IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF

Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

IMMUNOMODULATORY CONJUGATES

The present invention provides an immunomodulatory compound comprising a carbohydrate polymer comprising mannose, wherein the carbohydrate polymer is conjugated to at least one immune modulator. The present invention also provides for the use of this compound in immunomodulatory compositions for vaccination and gene therapy methods, together with processes for its preparation.

Process for preparing 1-substituted, 2-substituted 1H-imidazo[4, 5-c]quinoline-4-amines

Methods of preparing 1-substituted, 2-substituted 1H-imidazo [4-5c]-quinolin-4-amines are disclosed. The compounds function as antiviral agents, they induce the biosynthesis of various cytokines including interferon, and they inhibit tumor formation in animal models.