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Merck

I5159

Imiquimod

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

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C14H16N4
Número CAS:
99011-02-6
Peso molecular:
240.30
UNSPSC Code:
12352200
PubChem Substance ID:
24724516
NACRES:
NA.77
MDL number:
MFCD00866946
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

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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 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.
Imiquimod is a caspase 3 activator, which directly induces procaspase 3 cleavage to active caspase 3. Imiquimod induces apoptosis in vivo and acts as an immunomodulator with anti-viral and anti-inflammatory perties.
Imiquimod helps to induce the innate cutaneous immunity and the cellular arm of the adaptive immune response.

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

Clase de almacenamiento

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

wgk

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
0000413534
0000413534
0000436179
0000436179
0000338105

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Juandy Jo et al.
PLoS pathogens, 10(6), e1004210-e1004210 (2014-06-27)
The ability of innate immune cells to sense and respond to impending danger varies by anatomical location. The liver is considered tolerogenic but is still capable of mounting a successful immune response to clear various infections. To understand whether hepatic
Jessica A Pane et al.
PLoS pathogens, 10(3), e1003998-e1003998 (2014-03-29)
It has been proposed that rotavirus infection promotes the progression of genetically-predisposed children to type 1 diabetes, a chronic autoimmune disease marked by infiltration of activated lymphocytes into pancreatic islets. Non-obese diabetic (NOD) mice provide a model for the human
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
Tzu-Kai Lin et al.
Environmental toxicology, 39(9), 4360-4371 (2024-05-18)
The primary function of the skin is to form a mechanical, permeability, antimicrobial, and ultraviolet radiation barrier, which is essential for maintaining physiological homeostasis. Our previous studies demonstrated that cutaneous pigmentation could promote skin barrier function in addition to providing
M H Roozeboom et al.
The British journal of dermatology, 172(3), 739-745 (2014-07-30)
A recent noninferiority randomized controlled trial (RCT) indicated that imiquimod can be considered as superior to methylaminolevulinate photodynamic therapy (MAL-PDT) in the treatment of superficial basal cell carcinoma (sBCC). Knowledge of treatment effectiveness in subgroups of patients is of great
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