Product Name

Imiquimod

CAS Number

99011-02-06

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Product Name:
Imiquimod
CAS Number:
99011-02-06
Indication:
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.
Mode of Action:

Imiquimod's mechanism of action is via stimulation of innate and acquired immune responses, which ultimately leads to inflammatory cell infiltration within the field of drug application followed by apoptosis of diseased tissue. Imiquimod does not have direct antiviral activity. Studies of mice show that imiquimod may induce cytokines, including interferon-alpha (IFNA) as well as several IFNA genes (IFNA1, IFNA2, IFNA5, IFNA6, and IFNA8) as well as the IFNB gene. Imiquimod also induced the expression of interleukin (IL)-6, IL-8, and tumor necrosis factor alpha genes. In the treatment of basal cell carcinoma, Imiquimod appears to act as a toll-like receptor-7 agonist, and is thought to exert its anti-tumor effect via modification of the immune response and stimulation of apoptosis in BCC cells. In treating basal cell carcinoma it may increase the infiltration of lymphocytes, dendritic cells, and macrophages into the tumor lesion.

Pharmacodynamics:

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.

Toxicity:

Symptoms of overdose include flu-like symptoms, such as fever, fatigue, headache, nausea, diarrhoea and muscle pain.

IUPAC:
1-(2-methylpropyl)-1H-imidazo[4, 5-c]quinolin-4-amine
ATC:
D06BB10
PubChem:
57469
DrugBank:
DB00724 (APRD01030)
Formula:
C25H28N6O
Molecular Mass:
240.3036
Synonyms:
Imiquimod acetate
SMILES:
CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N
AHFS Code:
84:92.00
InChi:
DOUYETYNHWVLEO-UHFFFAOYSA-N
General Reference:
General Reference:

  1. Link
  2. van Egmond S, Hoedemaker C, Sinclair R: Successful treatment of perianal Bowenês disease with imiquimod. Int J Dermatol. 2007 Mar;46(3):318-9. Pubmed
  3. Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S: Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol. 2002 Feb;3(2):196-200. Epub 2002 Jan 22. Pubmed
  4. Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. Pubmed
  5. Miller RL, Gerster JF, Owens ML, Slade HB, Tomai MA: Imiquimod applied topically: a novel immune response modifier and new class of drug. Int J Immunopharmacol. 1999 Jan;21(1):1-14. Pubmed

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