I5159

Imiquimod

≥98% (HPLC), solid

• Synonym(s): 1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine
• Empirical Formula (Hill Notation): C₁₄H₁₆N₄
• CAS Number: 99011-02-6
• Molecular Weight: 240.30
• MDL number: MFCD00866946
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724516

Properties

• 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)

Description

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.

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301 - H315 - H319
• Precautionary Statements: P264 - P270 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• 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