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I5159

Sigma-Aldrich

Imiquimod

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C14H16N4
Numéro CAS:
Poids moléculaire :
240.30
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

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Nom du produit

Imiquimod, ≥98% (HPLC), solid

Essai

≥98% (HPLC)

Forme

solid

Solubilité

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

Chaîne SMILES 

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)

Clé InChI

DOUYETYNHWVLEO-UHFFFAOYSA-N

Informations sur le gène

human ... TLR7(51284)

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Description générale

Imiquimod is a toll-like receptor (TLR)-7/8 agonist.[1]

Application

Imiquimod has been used as TLR7 agonist for TLR7 agonist enhancement studies.[2] It has also been used as an NLR family, pyrin domain containing 3 (NLRP3) stimulant to treat NLRP3-FL-Btn and FLAG-ASC-FL.[3]

Actions biochimiques/physiologiques

Imiquimod helps to induce the innate cutaneous immunity and the cellular arm of the adaptive immune response.[1]
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.

Caractéristiques et avantages

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

Pictogrammes

Skull and crossbones

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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


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Consulter la Bibliothèque de documents

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
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
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
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

Questions

  1. Is imiquimod a cream?

    1 réponse
    1. This product is offered in a powdered format. Unless otherwise stated, this product is intended for research use only. It is not suitable for any other purpose, which includes, but is not limited to, unauthorized commercial use, in vitro diagnostic use, or therapeutic use in humans or animals.

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