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401020

Sigma-Aldrich

Imiquimod

An imidazoquinoline compound that acts as a potent immunomodulator and displays anti-angiogenic, anti-viral and anti-inflammatory properties.

Synonym(s):

Imiquimod, 1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine

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About This Item

Empirical Formula (Hill Notation):
C14H16N4
CAS Number:
Molecular Weight:
240.30
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

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

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

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

Cell permeable: no
Primary Target
TLR7 (toll-like receptor 7)
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Toxic (F)

Preparation Note

warming to 60°C is required for complete solubilization.

Reconstitution

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.

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

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

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


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Peishan Li et al.
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Cancer patients by immune checkpoint therapy have achieved long-term remission, with no recurrence of clinical symptoms of cancer for many years. Nevertheless, more than half of cancer patients are not responsive to this therapy due to immune exhaustion. Here, we

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