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I5159

Imiquimod

Name: Imiquimod
Brand: SIGMA

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

Synonym(s):

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

PubChem Substance ID:

24724516

NACRES:

NA.77

MDL number:

MFCD00866946

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Properties

Product Name

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)

Description

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.

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.

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.

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pictograms

GHS06

signalword

Danger

hcodes

H301,H315,H319

pcodes

P264 - P270 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338

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

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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Photodynamic therapy versus topical imiquimod versus topical fluorouracil for treatment of superficial basal-cell carcinoma: a single blind, non-inferiority, randomised controlled trial.

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

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)

IL-23 from Langerhans cells is required for the development of imiquimod-induced psoriasis-like dermatitis by induction of IL-17A-producing γδ T cells.

Ryutaro Yoshiki et al.

The Journal of investigative dermatology, 134(7), 1912-1921 (2014-02-27)

Psoriasis is a common chronic inflammatory skin disease that involves dysregulated interplay between immune cells and keratinocytes. Recently, it has been reported that IL-23 induces CCR6+ γδ T cells, which have the pivotal role in psoriasis-like skin inflammation in mice

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Global Trade Item Number

SKU	GTIN
I5159-200MG	04061833857182