1338313

Imiquimod

United States Pharmacopeia (USP) Reference Standard

• Synonym(s): Imiquimod, 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
• NACRES: NA.24
• PubChem Substance ID: 329750158
• UNSPSC Code: 41116107
• MDL number: MFCD00866946

Properties

• grade: pharmaceutical primary standard
• API family: imiquimod
• manufacturer/tradename: USP
• application(s): pharmaceutical (small molecule)
• format: neat
• 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

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.
For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Imiquimod USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:

• Imiquimod Cream

Biochem/physiol Actions

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.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301,H315,H319
• pcodes: P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338 - P332 + P313
• 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: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable