Imiquimod

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Imiquimod
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Clinical data
[[Regulation of therapeutic goods \|Template:Engvar data]]	EU EMA: by INN; US FDA: Imiquimod;
Pregnancy; category	AU: B1 ; US: C (Risk not ruled out) ; ;
Routes of; administration	Topical
ATC code	D06BB10 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only) ; US: ℞-only ;
Pharmacokinetic data
Elimination half-life	20 hours (topical dose), 2 hours (subcutaneous dose)
Identifiers
	IUPAC name 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine;
CAS Number	99011-02-6;
PubChem CID	57469;
DrugBank	APRD01030;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C14H16N4
Molar mass	240.304 g/mol

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Overview

Imiquimod (INN, marketed by 3M under the trade name Aldara) is a prescription medication that acts as an immune response modifier.

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.

It is also used pre-operatively to shrink basal cell cancer and melanoma in situ (especially Lentigo Maligna) before Mohs surgery.

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]

References

↑ 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.
↑ 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.
↑ Sauder, D.N., Imiquimod: modes of action. British Journal of Dermatology. 2003 149(Suppl. 66):5-8. PMID 14616337
↑ ^4.0 ^4.1 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

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de:Imiquimod nl:Imiquimod th:อีมิควิมอด Template:Jb1

Template:WikiDoc Sources

[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.

[Evans-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.

[Sauder-3] Sauder, D.N., Imiquimod: modes of action. British Journal of Dermatology. 2003 149(Suppl. 66):5-8. PMID 14616337

[Miller-4] 4.0 ^4.1 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

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v t e Antibiotics and chemotherapeutics for dermatological use (D06)
Antibiotics: tetracycline and derivatives	Demeclocycline - Chlortetracycline - Oxytetracycline - Tetracycline
Antibiotics: other	Fusidic acid - Chloramphenicol - Neomycin - Bacitracin - Gentamicin - Tyrothricin - Mupirocin - Nadifloxacin - Virginiamycin - Rifaximin - Amikacin
Chemotherapeutics: sulfonamides	Silver sulfadiazine - Sulfathiazole - Mafenide - Sulfamethizole - Sulfanilamide - Sulfamerazine
Chemotherapeutics: antivirals	Idoxuridine - Tromantadine - Aciclovir - Podophyllotoxin - Inosine - Penciclovir - Lysozyme - Ibacitabine - Edoxudine - Imiquimod - Docosanol
Chemotherapeutics: other	Metronidazole

v t e Antivirals, other than for HIV (primarily J05, also S01AD and D06BB)
Anti-herpesvirus (DNA, I)	guanine analogues (Aciclovir, Famciclovir, Ganciclovir, Penciclovir, Valaciclovir, Valganciclovir) • nucleoside analogues (Idoxuridine, Trifluridine, Vidarabine) • Cidofovir • Docosanol • Fomivirsen • Foscarnet • Tromantadine
HPV/MC (DNA, I)	Imiquimod • Podophyllotoxin
Hepatitis B (DNA, VII)	Adefovir • Interferon alfa-2b • Pegylated interferon alfa-2a • Entecavir • Lamivudine • Telbivudine • Tenofovir^†
Hepatitis C (RNA, IV)	Pegylated interferon alpha • Ribavirin • Taribavirin^† • Boceprevir^†
Picornavirus (RNA, IV)	Pleconaril^†
Anti-influenza agents (RNA, V)	Arbidol adamantane derivatives/M2 inhibitors (Amantadine, Rimantadine) neuraminidase inhibitors (Oseltamivir, Zanamivir, Peramivir^†)
HIV (Reverse, VI)	See HIV pharm
Other antiviral agents	general (Inosine, Interferon)
^†Undergoing clinical trials, not FDA approved.