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Encyclopedia > Imiquimod
Imiquimod
Systematic (IUPAC) name
1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
Identifiers
CAS number 99011-02-6
ATC code D06BB10
PubChem 57469
DrugBank APRD01030
Chemical data
Formula C14H16N4 
Mol. mass 240.304 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life 20 hours (topical dose), 2 hours (subcutaneous dose)
Excretion  ?
Therapeutic considerations
Licence data

EU US Image File history File links Imiquimod. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... BIC pen cap, about 1 gram. ... The mole (symbol: mol) is the SI base unit that measures an amount of substance. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Pregnancy cat.

B1(AU) C(US) The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

POM(UK) -only(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Routes Topical

Imiquimod (INN, marketed by 3M under the trade name Aldara) is a prescription medication that acts as an immune response modifier. Sometimes they put hydrocortisone cream which is really cheap and is sold at Wal Mart. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... 3M Company (NYSE: MMM), formerly Minnesota Mining and Manufacturing Company until 2002, is an American corporation with a worldwide presence. ...

Contents

Uses

Imiquimod is a patient-applied cream used to treat certain diseases of the skin, including skin cancer (basal cell carcinoma, Bowen's disease[1], superficial squamous cell carcinoma, some superfical malignant melanomas and actinic keratosis) as well as genital warts (Condylomata Acuminata). It has also been tested for treatment of Molluscum contagiosum. It causes interferon production which triggers the patient's immune response against these tumors. Skin cancer is a malignant growth on the skin which can have many causes. ... Basal cell carcinoma (BCC) is the most common skin cancer. ... In medicine (dermatology), Bowens disease (BD) is a sunlight-induced skin disease, considered either as an early stage or intraepidermal form of squamous cell carcinoma. ... Biopsy of a highly differentiated squamous cell carcinoma of the mouth. ... Melanoma is a malignant tumor of melanocytes. ... Actinic keratosis (also called solar keratosis, senile keratosis, or AK) is a premalignant condition of thick, scaly, or crusty patches of skin. ... Genital warts or (or condyloma) is a very contagious sexually transmitted disease. ... Molluscum contagiosum (MC) is a viral infection of the skin or occasionally of the mucous membranes. ... Interferons (IFNs) are natural proteins produced by the cells of the immune system of most vertebrates in response to challenges by foreign agents such as viruses, bacteria, parasites and tumor cells. ...


It is also used pre-operatively to shrink basal cell cancer and melanoma in situ (especially Lentigo Maligna) before Mohs surgery. Mohs Surgery, created by Dr. Fredrick E. Mohs, is microscopically controlled surgery that is highly effective for common types of skin cancer, with a cure rate of up to 99% for basal cell carcinoma, the most common type of skin cancer, and for squamous cell carcinoma. ...


Side effects include redness and irritation of the skin during treatment.


History

The original FDA approval was on February 27, 1997, FDA Application No. (NDA) 020723, by Graceway.


Since then, the label has been revised many times. Adverse side effects have been reported, in some cases serious and systemic. Some patients have been suffering from severe auto-immune or neuro-immune effects for years.[citation needed]


Mechanism of action

The exact mode in which imiquimod and its analogs activate the immune system is not yet known. Nevertheless, it is known that Imiquimod activates immune cells by ligating the toll-like receptor 7 (TLR7), commonly involved in pathogen recognition, on the cell surface.[2] Cells activated by imiquimod via TLR-7 secrete cytokines (primarily interferon-α (IFN-α), interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α)). [3] There is evidence that imiquimod, when applied to skin, can lead to the activation of Langerhans cells, which subsequently migrates to local lymph nodes to activate the adaptive immune system.[4] Other cell types activated by imiquimod include natural killer cells, macrophages and B-lymphocytes.[4] It has been suggested that this article or section be merged with ligand. ... TLR 7 is a toll-like receptor. ... Cytokines are small protein molecules that are the core of communication between immune system cells, and even between immune system cells and cells belonging to other tissue types. ... The 3D structure of human IFN-β Human type I interferons comprise a vast and growing group of IFN proteins. ... Interleukin-6 (IL-6) is a pro-inflammatory cytokine secreted by T cells and macrophages to stimulate immune response to trauma, especially burns or other tissue damage leading to inflammation. ... In medicine, tumor necrosis factor alpha (TNFα, cachexin or cachectin) is an important cytokine involved in systemic inflammation and the acute phase response. ... Langerhans cells are immature dendritic cells containing large granules called Birbeck granules. ... Natural killer cells (NK) are a type of lymphocyte (a white blood cell) and a component of nonspecific immune defense. ... Macrophages (Greek: big eaters) are cells found in tissues that are responsible for phagocytosis of pathogens, dead cells and cellular debris. ... B cells are lymphocytes that play a large role in the humoral immune response (as opposed to the cell-mediated immune response). ...


References

  1. ^ van Egmond S, Hoedemaker C, Sinclair R (2007). "Successful treatment of perianal Bowen's disease with imiquimod". Int J Dermatol 46 (3): 318-9. PMID 17343595. 
  2. ^ Hemmi, H., et al. Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol.. 2002 3(2):196-200. PMID 11812998.
  3. ^ Sauder, D.N., Imiquimod: modes of action. British Journal of Dermatology. 2003 149(Suppl. 66):5-8. PMID 14616337
  4. ^ a b Miller, R.L., et al. Imiquimod applied topically: a novel immune response modifier and a new class of drug. Int J Immunopharmacol. 1999 Jan;21(1):1-14. PMID 10411278

External links


  Results from FactBites:
 
Imiquimod 5 percent cream and the treatment of cutaneous malignancy (3824 words)
Imiquimod resembles a nucleoside analogue and is known for its potent induction of endogenous antiviral pro-inflammatory mediators.
Imiquimod resembles a nucleoside analogue (fig.1) and is known for its potent induction of endogenous antiviral pro-inflammatory mediators [1].
The addition of imiquimod resulted in the induction of Fas receptors on tumor cells, and is postulated to lead to their subsequent apoptosis via binding of FasR to the Fas ligand, induction by neighboring BCC cells, and infiltration of lymphocytes.
Imiquimod for genital warts (623 words)
With imiquimod 5%, 72% (67% to 78%) of patients had the outcome, compared with 20% (15% to 25%) with placebo.
This means that two patients have to be treated with 5% imiquimod for 8 to 16 weeks for one of them to have wart area reduced by at least 50%.
This means that three patients have to be treated with 5% imiquimod for 8 to 16 weeks for one of them to have warts completely cleared, and for them not to recur.
  More results at FactBites »

 
 

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