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Safety Information

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

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)

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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.
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.

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000338105
0000241002
0000241002
0000338105
0000263624

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Microglial-derived miRNA let-7 and HMGB1 contribute to ethanol-induced neurotoxicity via TLR7
Coleman L G, et al.
Journal of Neuroinflammation, 14(1), 22-22 (2017)
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)
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
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
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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