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I5159

Sigma-Aldrich

Imiquimod

≥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
MDL number:
MFCD00866946
UNSPSC Code:
12352200
PubChem Substance ID:
24724516
NACRES:
NA.77

product name

Imiquimod, ≥98% (HPLC), solid

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

Signal Word

Danger

Hazard Statements

H301,H315,H319

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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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