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I5159
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:
Molecular Weight:
240.30
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.
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Product Name
Imiquimod, ≥98% (HPLC), solid
Quality Level
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.[1]
Application
Biochem/physiol Actions
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.
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
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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
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
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
Poly (I: C) and hyaluronic acid directly interact with NLRP3, resulting in the assembly of NLRP3 and ASC in a cell-free system
Kaneko N, et al.
European journal of inflammation, 15(2), 85-97 (2017)
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