Imiquimod
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
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-23 17:50:46
What is Imiquimod?
Absorption
Well absorbed through skin (as a cream)
Toxicity
Symptoms of overdose include flu-like symptoms, such as fever, fatigue, headache, nausea, diarrhoea and muscle pain.
Description
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.
The Uses of Imiquimod
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.
Indications
For the topical treatment of clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratoses on the face or scalp in immunocompetent adults. Also indicated for the treatment of external genital and perianal warts/condyloma acuminata in individuals 12 years old and above.
Background
Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. Miquimod is also used to treat a skin condition of the face and scalp called actinic keratoses and certain types of skin cancer called superficial basal cell carcinoma.
What are the applications of Application
Imiquimod is a TLR7 activator and angiogenesis inhibitor
Pharmacokinetics
Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. It is not used on warts inside the vagina, penis, or rectum. Imiquimod is also used to treat a skin condition of the face and scalp called actinic keratoses. Imiquimod can also be used to treat certain types of skin cancer called superficial basal cell carcinoma. Imiquimod is particularly useful on areas where surgery or other treatments may be difficult, complicated or otherwise undesirable, especially the face and lower legs.
Metabolism
Not Available
Properties of Imiquimod
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 |
color | White |
Water Solubility | Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol. |
Safety information for Imiquimod
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Imiquimod
InChIKey | DOUYETYNHWVLEO-UHFFFAOYSA-N |
Abamectin manufacturer
Solara Active Pharma Sciences Ltd
Ralington Pharma
BDR Pharmaceuticals International Pvt Ltd
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