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I5159

Sigma-Aldrich

Imiquimod

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

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C14H16N4
CAS-Nummer:
99011-02-6
Molekulargewicht:
240.30
MDL-Nummer:
MFCD00866946
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24724516
NACRES:
NA.77

Produktbezeichnung

Imiquimod, ≥98% (HPLC), solid

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

solid

Löslichkeit

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)

InChIKey

DOUYETYNHWVLEO-UHFFFAOYSA-N

Angaben zum Gen

human ... TLR7(51284)

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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

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Analysenzertifikate (COA)

Lot/Batch Number
0000338105
0000338105
0000241002
0000263624
0000205587

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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
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
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
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
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