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I5159

Sigma-Aldrich

Imiquimod

≥98% (HPLC), solid

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Synonym(s):
1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine
Empirical Formula (Hill Notation):
C14H16N4
CAS Number:
Molecular Weight:
240.30
MDL number:
PubChem Substance ID:

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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This Item
1338313401020SML0877
vibrant-m

I5159

Imiquimod

vibrant-m

1338313

Imiquimod

vibrant-m

401020

Imiquimod

vibrant-m

SML0877

Gardiquimod

assay

≥98% (HPLC)

assay

-

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

solubility

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

solubility

-

solubility

DMSO: 3 mg/mL

solubility

DMSO: 10 mg/mL, clear

Gene Information

human ... TLR7(51284)

Gene Information

human ... TLR7(51284)

Gene Information

-

Gene Information

-

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

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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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
Anne Walter et al.
Nature communications, 4, 1560-1560 (2013-03-07)
Aldara is a cream used for topical treatment of non-melanoma skin cancer, and is thought to act through stimulation of anti-tumour immunity. The active ingredient, imiquimod, has been shown to stimulate toll-like receptor 7. Aldara also induces psoriasis-like lesions when
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
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
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

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