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I5159

Sigma-Aldrich

Imiquimod

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C14H16N4
Número de CAS:
99011-02-6
Peso molecular:
240.30
MDL number:
MFCD00866946
UNSPSC Code:
12352200
PubChem Substance ID:
24724516
NACRES:
NA.77
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Nombre del producto

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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Este artículo
1338313401020SML0877
Imiquimod &#8805;98% (HPLC), solid

I5159

Imiquimod

Imiquimod United States Pharmacopeia (USP) Reference Standard

1338313

Imiquimod

Imiquimod An imidazoquinoline compound that acts as a potent immunomodulator and displays anti-angiogenic, anti-viral and anti-inflammatory properties.

401020

Imiquimod

Gardiquimod &#8805;98% (HPLC)

SML0877

Gardiquimod

form

solid

form

-

form

solid

form

powder

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

solubility

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

solubility

-

solubility

DMSO: 3 mg/mL

solubility

DMSO: 10 mg/mL, clear

Gene Information

human ... TLR7(51284)

Gene Information

human ... TLR7(51284)

Gene Information

-

Gene Information

-

General description

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]

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.
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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

    • Elija entre una de las versiones más recientes:

    Certificados de análisis (COA)

    Lot/Batch Number
    065M4746V
    074M4751V
    053M4706V
    042M4704V
    081M4740V

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    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
    Ryutaro Yoshiki et al.
    The Journal of investigative dermatology, 134(7), 1912-1921 (2014-02-27)
    Psoriasis is a common chronic inflammatory skin disease that involves dysregulated interplay between immune cells and keratinocytes. Recently, it has been reported that IL-23 induces CCR6+ γδ T cells, which have the pivotal role in psoriasis-like skin inflammation in mice
    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)
    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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