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| Imiquimod | |
| Systematic (IUPAC) name | |
| 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine | |
| Identifiers | |
| CAS number | |
| ATC code | D06 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C14H16N4 |
| Mol. mass | 240.304 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | 20 hours (topical dose), 2 hours (subcutaneous dose) |
| Excretion | ? |
| Therapeutic considerations | |
| Licence data |
, |
| Pregnancy cat. | |
| Legal status | |
| Routes | Topical |
Imiquimod (INN) is a prescription medication that acts as an immune response modifier. It is marketed by MEDA AB, Graceway Pharmaceuticals and iNova Pharmaceuticals under the trade name Aldara and by Mochida as Beselna.
Contents |
Imiquimod is a patient-applied cream used to treat certain diseases of the skin, including skin cancers (basal cell carcinoma, Bowen\'s diseasevan 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. , superficial squamous cell carcinoma, some superficial malignant melanomas, and actinic keratosis) as well as genital warts (Condylomata acuminata). It has also been tested for treatment of Molluscum contagiosum and VAIN (vaginal intraepithelial neoplasia).Buck HW, Guth KJ. "Treatment of vaginal intraepithelial neoplasia (primarily low grade) with imiquimod 5% cream.". J Low Genit Tract Dis. PMID 17051086.
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.
The exact mechanism of action 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.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. 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)). Sauder, D.N., Imiquimod: modes of action. British Journal of Dermatology. 2003 149(Suppl. 66):5-8. PMID 14616337 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.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 Other cell types activated by imiquimod include natural killer cells, macrophages and B-lymphocytes.
| 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 - 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 |
| 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† |
| 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. | |
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