401020

Imiquimod

≥98% (HPLC), TLR7 agonist, solid

• Synonym(s): Imiquimod, 1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine
• Empirical Formula (Hill Notation): C₁₄H₁₆N₄
• CAS Number: 99011-02-6
• Molecular Weight: 240.30
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00866946
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• Product Name: Imiquimod, An imidazoquinoline compound that acts as a potent immunomodulator and displays anti-angiogenic, anti-viral and anti-inflammatory properties.
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: 3 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [n]1(c2c(nc1)c(nc3c2cccc3)N)CC(C)C
• InChI: 1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
• InChI key: DOUYETYNHWVLEO-UHFFFAOYSA-N

Description

General description

An imidazoquinoline compound that acts as a potent immunomodulator and displays anti-angiogenic, anti-viral and anti-inflammatory properties. Reported to bind to the cell surface receptor, TLR7 (toll-like receptor 7), and induce the secretion of several pro-inflammatory cytokines and chemokines both in vitro and in vivo.

Biochem/physiol Actions

Primary Target
TLR7 (toll-like receptor 7)

Product does not compete with ATP.

Reversible: no

Cell permeable: no

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C. Upon thawing, warming may be required to resolubilize precipitated product.

warming to 60°C is required for complete solubilization.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Majewski, S., et al. 2005. Int. J. Dermatol.44, 14.
Gibson, S.J., et al. 2002. Cell. Immunol.218, 74.
Hemmi, H., et al. 2002. Nat. Immunol.3, 196.
Megyeri, K., et al. 1995. Mol. Cell. Biol.15, 2207.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Toxic (F)

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301,H315,H319
• pcodes: P264 - P270 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable