Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H16N4 |
Molecular Weight | 240.3042 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)Cn1cnc2c1c3ccccc3[nH]c2=N
InChI
InChIKey=DOUYETYNHWVLEO-UHFFFAOYSA-N
InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
DescriptionSources: http://www.drugbank.ca/drugs/DB00724Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/cdi/imiquimod.html
Sources: http://www.drugbank.ca/drugs/DB00724
Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/cdi/imiquimod.html
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. 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. Imiquimod is used 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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL614917 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24966637 |
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Target ID: CHEMBL2157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22128302 |
16.9 µM [EC50] | ||
Target ID: P22301 Gene ID: 3586.0 Gene Symbol: IL10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22128302 |
17.0 µM [EC50] | ||
Target ID: CHEMBL5936 Sources: http://www.drugbank.ca/drugs/DB00724 |
2.12 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Aldara Approved UseAldara Cream is indicated for the topical treatment of:
• Clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratoses (AK) on the face or scalp in immunocompetent adults
• Biopsy-confirmed, primary superficial basal cell carcinoma (sBCC) in immunocompetent adults; maximum tumor diameter
of 2.0 cm on trunk, neck, or extremities (excluding hands and feet), only when surgical methods are medically less appropriate
and patient follow-up can be reasonably assured.
• External genital and perianal warts/condyloma acuminata in patients 12 years old or older Launch Date8.57088E11 |
|||
Primary | Aldara Approved UseAldara Cream is indicated for the topical treatment of:
• Clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratoses (AK) on the face or scalp in immunocompetent adults
• Biopsy-confirmed, primary superficial basal cell carcinoma (sBCC) in immunocompetent adults; maximum tumor diameter
of 2.0 cm on trunk, neck, or extremities (excluding hands and feet), only when surgical methods are medically less appropriate
and patient follow-up can be reasonably assured.
• External genital and perianal warts/condyloma acuminata in patients 12 years old or older Launch Date8.57088E11 |
|||
Primary | Aldara Approved UseAldara Cream is indicated for the topical treatment of:
• Clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratoses (AK) on the face or scalp in immunocompetent adults
• Biopsy-confirmed, primary superficial basal cell carcinoma (sBCC) in immunocompetent adults; maximum tumor diameter
of 2.0 cm on trunk, neck, or extremities (excluding hands and feet), only when surgical methods are medically less appropriate
and patient follow-up can be reasonably assured.
• External genital and perianal warts/condyloma acuminata in patients 12 years old or older Launch Date8.57088E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
120 ng/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIQUIMOD plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.1 ng/mL |
12.5 mg 3 times / week steady-state, topical dose: 12.5 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
IMIQUIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
573 ng × h/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIQUIMOD plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.7 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIQUIMOD plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
5 % 3 times / week multiple, topical Recommended Dose: 5 %, 3 times / week Route: topical Route: multiple Dose: 5 %, 3 times / week Sources: Page: p.2400 |
unhealthy, 35±6.9 n = 65 Health Status: unhealthy Condition: Anogenital warts Age Group: 35±6.9 Sex: M+F Population Size: 65 Sources: Page: p.2400 |
Disc. AE: Localised skin reaction... AEs leading to discontinuation/dose reduction: Localised skin reaction (1.5%) Sources: Page: p.2400 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Localised skin reaction | 1.5% Disc. AE |
5 % 3 times / week multiple, topical Recommended Dose: 5 %, 3 times / week Route: topical Route: multiple Dose: 5 %, 3 times / week Sources: Page: p.2400 |
unhealthy, 35±6.9 n = 65 Health Status: unhealthy Condition: Anogenital warts Age Group: 35±6.9 Sex: M+F Population Size: 65 Sources: Page: p.2400 |
PubMed
Title | Date | PubMed |
---|---|---|
Topical imiquimod treatment of human papillomavirus in a patient with human immunodeficiency virus. | 2001 Aug-Sep |
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Successful topical immunotherapy of bowenoid papulosis with imiquimod. | 2001 Dec |
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Imiquimod and resiquimod as novel immunomodulators. | 2001 Dec |
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Fighting infection using immunomodulatory agents. | 2001 Jul |
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[Anal condyloma: its management is still difficult]. | 2001 Oct |
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Topical immunomodulators--progress towards treating inflammation, infection, and cancer. | 2001 Oct |
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[Disseminated actinic keratoses. Comparison of topical photodynamic therapy with 5-aminolevulinic acid and topical 5% imiquimod cream]. | 2001 Oct |
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Treatment of human papilloma virus in a 6-month-old infant with imiquimod 5% cream. | 2001 Sep-Oct |
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Treatment of anogenital warts in children with topical 0.05% podofilox gel and 5% imiquimod cream. | 2001 Sep-Oct |
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Imiquimod 5% cream in the treatment of human papillomavirus-16-positive erythroplasia of Queyrat. | 2002 |
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New treatment modalities for basal cell carcinoma. | 2002 |
|
Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment. | 2002 |
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Viral diseases of the skin: diagnosis and antiviral treatment. | 2002 |
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[Perspectives for the treatment and prevention of herpes simplex infections]. | 2002 Apr |
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Human papillomavirus: a review. | 2002 Apr |
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'Rub on' treatment for basal-cell carcinoma. | 2002 Apr |
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Clinical inquiries. What is the most effective treatment for external genital warts? | 2002 Apr |
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Treatment of a large superficial basal cell carcinoma with 5% imiquimod: a case report and review of the literature. | 2002 Apr |
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The effects of 5% imiquimod cream on high-grade vulval intraepithelial neoplasia. | 2002 Apr |
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Squamous cell carcinoma in situ of the penis successfully treated with imiquimod 5% cream. | 2002 Apr |
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To cut a long story short - the use of imiquimod in resistant warts. | 2002 Apr |
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Treatment of high-grade vaginal intraepithelial neoplasia with imiquimod cream. | 2002 Aug 1 |
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[Pharma clinics. Medication of the month. Imiquimod (Aldara): an immunomodulator for the skin]. | 2002 Feb |
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Porokeratosis of Mibelli: successful treatment with 5% imiquimod cream. | 2002 Feb |
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Increased frequency of dosing of imiquimod 5% cream in the treatment of external genital warts in women. | 2002 Feb |
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Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. | 2002 Feb |
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Experimental nonsurgical tattoo removal in a guinea pig model with topical imiquimod and tretinoin. | 2002 Jan |
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Imiquimod 5% cream is an acceptable treatment option for external anogenital warts in uncircumcised males. | 2002 Jan |
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Recent advances in dermatology. | 2002 Jan |
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The importance of patient and healthcare provider perceptions in the evaluation of imiquimod and other prior treatments for anogenital warts. | 2002 Jan |
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Topical imiquimod 5% cream in the treatment of Bowen's disease of the penis. | 2002 Jan |
|
The epidemiology and treatment of anogenital warts in Singapore: a retrospective evaluation. | 2002 Jul |
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Successful treatment of anogenital Bowen's disease with the immunomodulator imiquimod, and monitoring of therapy by DNA image cytometry. | 2002 Jul |
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Imiquimod: a potential role in dermatology? | 2002 Jul |
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Infantile hemangioma: clinical resolution with 5% imiquimod cream. | 2002 Jul |
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Efficacy of imiquimod on external anogenital warts in HIV-infected patients previously treated by highly active antiretroviral therapy. | 2002 Jul 5 |
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Treatment of non-genital warts with topical imiquimod 5% cream. | 2002 Jul-Aug |
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Gateways to Clinical Trials. June 2002. | 2002 Jun |
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Imiquimod 5% cream in the treatment of anogenital warts in female patients. | 2002 Jun |
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New treatments for actinic keratoses. | 2002 Jun 24 |
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Infectious diseases. 6: Sexually transmitted infections: new diagnostic approaches and treatments. | 2002 Jun 3 |
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Immunomodulation as a treatment strategy for genital herpes: review of the evidence. | 2002 Mar |
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Gateways to clinical trials. | 2002 May |
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Imiquimod 5% cream: a new treatment option for basal cell carcinoma. | 2002 May |
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Imiquimod 5% cream: a topical immune response modifier. | 2002 May |
|
Treatment of vulvar intraepithelial neoplasia 2/3 with imiquimod. | 2002 May |
|
Successful treatment of multiple superficial basal cell carcinomas with topical imiquimod: case report and review of the literature. | 2002 May |
|
Topical imiquimod cream 5% for resistant perianal warts in a renal transplant patient. | 2002 May |
|
Efficacy of imiquimod 5% cream in the treatment of recalcitrant warts in children. | 2002 May-Jun |
|
Safety studies of topical imiquimod 5% cream on normal skin exposed to ultraviolet radiation. | 2002 Sep 2 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/imiquimod-topical.html
Actinic Keratosis:
2.5% and 3.75% cream: Apply topically to the affected area (either entire face or balding scalp) once a day prior to bedtime. Up to 0.5 g (2 packets or 2 full actuations of the pump) may be applied to the treatment area at each application.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24966637
Invasion of SK-MEL-24 cells was significantly decreased by 43.87% and 67.02% after treatment with 10 and 30 ug/ml imiquimod, respectively, as compared with non-treated SK-MEL-24 cells
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000009267
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WHO-VATC |
QD06BB10
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WHO-ATC |
D06BB10
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FDA ORPHAN DRUG |
425314
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NCI_THESAURUS |
C129820
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NDF-RT |
N0000009267
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NDF-RT |
N0000009269
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NDF-RT |
N0000000157
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EMA ASSESSMENT REPORTS |
ALDARA (AUTHORIZED: CONDYLOMATA ACUMINATA)
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NDF-RT |
N0000009269
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FDA ORPHAN DRUG |
707519
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EMA ASSESSMENT REPORTS |
ZARTRA (WITHDRAWN: CONDYLOMATA ACUMINATA)
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6911
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C056493
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M6234
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57469
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5003
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1338313
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CHEMBL1282
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1429
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99011-02-6
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IMIQUIMOD
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99011-02-6
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DB00724
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P1QW714R7M
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59943
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8129
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C1431
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SUB12453MIG
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Imiquimod
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ACTIVE MOIETY
METABOLITE (PARENT)