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I5159

Sigma-Aldrich

Imiquimod

≥98% (HPLC), solid, caspase 3 activator

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C14H16N4
Número de CAS:
99011-02-6
Peso molecular:
240.30
MDL number:
MFCD00866946
UNSPSC Code:
12352200
PubChem Substance ID:
24724516
NACRES:
NA.77

Nombre del producto

Imiquimod, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

solubility

H2O: <2 mg/mL
DMSO: 4 mg/mL (warming to 60 °C for 15 minutes)

SMILES string

CC(C)Cn1cnc2c(N)nc3ccccc3c12

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

Gene Information

human ... TLR7(51284)

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General description

Imiquimod is a toll-like receptor (TLR)-7/8 agonist.

Application

Imiquimod has been used as TLR7 agonist for TLR7 agonist enhancement studies. It has also been used as an NLR family, pyrin domain containing 3 (NLRP3) stimulant to treat NLRP3-FL-Btn and FLAG-ASC-FL.

Biochem/physiol Actions

Imiquimod helps to induce the innate cutaneous immunity and the cellular arm of the adaptive immune response.
Imiquimod is a caspase 3 activator, which directly induces procaspase 3 cleavage to active caspase 3. Imiquimod induces apoptosis in vivo in basal cell carcinoma. Its anti-tumor activity is related to the induction of apoptosis. Imiquimod has anti-angiogenic, anti-inflammatory, anti-viral activities. Imiquimod also acts as an immune response modulator inducing the secretion of various cytokines and chemokines.

Features and Benefits

This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
0000338105
0000338105
0000241002
0000263624
0000205587

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Topical imiquimod is and effective and safe drug for molluscum contagiosum in children
Badavanis G, et al.
Acta Dermatovenerologica Croatica, 25(2), 164-164 (2017)
Aimée H M M Arits et al.
The Lancet. Oncology, 14(7), 647-654 (2013-05-21)
Superficial basal-cell carcinoma is most commonly treated with topical non-surgical treatments, such as photodynamic therapy or topical creams. Photodynamic therapy is considered the preferable treatment, although this has not been previously tested in a randomised control trial. We assessed the
Poly (I: C) and hyaluronic acid directly interact with NLRP3, resulting in the assembly of NLRP3 and ASC in a cell-free system
Kaneko N, et al.
European journal of inflammation, 15(2), 85-97 (2017)
H Vinter et al.
The British journal of dermatology, 172(2), 345-353 (2014-07-02)
The application of Aldara(®) cream containing 5% imiquimod stimulates Toll-like receptor 7/8 on plasmacytoid dendritic cells, thereby producing a potent immunomodulatory effect. This has been reported to trigger psoriasis. To establish a human model of Aldara-induced psoriasis-like skin inflammation in
Olivier Richel et al.
The Lancet. Oncology, 14(4), 346-353 (2013-03-19)
Anal cancer is an increasing issue in HIV-positive men who have sex with men (MSM). Screening for its precursor, anal intraepithelial neoplasia (AIN), is subject of discussion. Current treatment options are suboptimum and have not been compared in a prospective
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