Imiquimod , 2mMinDMSO , 99011-02-6

Synonym(s):
1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine;1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine;Imiquimod;Imiquimod - CAS 99011-02-6 - Calbiochem

CAS NO.：99011-02-6

Empirical Formula: C14H16N4

Molecular Weight: 240.3

MDL number: MFCD00866946

EINECS: 619-387-8

PRODUCT Properties

• Melting point: 292-294°C
• Boiling point: 456.7±48.0 °C(Predicted)
• Density: 1.28±0.1 g/cm3(Predicted)
• storage temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• solubility: DMSO: soluble
• form: White solid
• pka: 6.28±0.30(Predicted)
• color: White
• Water Solubility: Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol.
• λmax: 245nm(H2O/MeOH)(lit.)
• Merck: 14,4922
• Stability: Incompatible with strong oxidizing agents.
• InChIKey: DOUYETYNHWVLEO-UHFFFAOYSA-N

Description and Uses

Aldara was launched in the US for the topical treatment of genital warts caused by human papillomavirus (HPV). It can be prepared in a six step approach beginning with the nucleophilic substitution of 4-chloro-3-nitroquinolone with isobutylamine or via a thermal electrocyclic ring closure of 1 - and 2-azahexatriene systems. Aldara has antiviral and antitumor properties, with the former activity arising from the induction of cytokines, in particular, INF-α. Aldara also induces TNF-γ, IL-1α, IL-1β, IL-1ra, IL-6, IL-8, IL-10, GM-CSF, G-CSF and MID-la formation 1-4 hr after stimuli. The exact cells responsible for the response have not been determined, however, it is not activating T lymphocytes, NK cells, B lymphocytes, or dendritic stem cells but monocytes (CD14⁺, CD36⁺, HLA-DR⁺, HLA-DQ^±, CD19^-, CD16^- and CD23^-) are partly responsible. The speculation is that Aldara may interact with a kinase modulating the transduction pathway leading to cytokine genes. There is no direct antiviral activity (induction of IFN does not follow true dose response) and it is not mutagenic. The hydroxylated metabolite also induces IFN-α.

Imiquimod is a caspase 3 activator which acts as an immunomodulator and displays antiviral and anti-tumor activity. It is a patient-applied cream used for the treatment of genital warts and basal cell carcinoma. It is also used to cure actinic keratosis on the face and scalp. It belongs to a group of drugs called immune response modifiers, which work by activating the immune system to fight abnormal skin growth.

Safety

• Symbol(GHS): GHS06
• Signal word: Danger
• Hazard statements: H301-H315-H319
• Precautionary statements: P264-P270-P280-P301+P310-P302+P352-P305+P351+P338
• Hazard Codes: T,Xi
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45-36/37/39-27
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NJ5903450
• HazardClass: 6.1
• PackingGroup: III
• HS Code: 29339900