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Merck
CN

401020

Imiquimod

≥98% (HPLC), TLR7 agonist, solid

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:
99011-02-6
Molecular Weight:
240.30
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00866946

Key Documents

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Product Name

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

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

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

Quality Level

100

Related Categories

Preparation Note

warming to 60°C is required for complete solubilization.
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.

Legal Information

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

Biochem/physiol Actions

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

Disclaimer

Toxicity: Toxic (F)

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.

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.

Packaging

Packaged under inert gas

pictograms

Skull and crossbones
GHS06

signalword

Danger

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

Certificates of Analysis (COA)

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Peishan Li et al.
Bioactive materials, 34, 466-481 (2024-01-31)
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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