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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
Structure of IMIQUIMOD

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)

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
16.9 µM [EC50]
Target ID: P22301
Gene ID: 3586.0
Gene Symbol: IL10
Target Organism: Homo sapiens (Human)
17.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Aldara

Approved Use

Aldara 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 Date

8.57088E11
Primary
Aldara

Approved Use

Aldara 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 Date

8.57088E11
Primary
Aldara

Approved Use

Aldara 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 Date

8.57088E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Successful topical immunotherapy of bowenoid papulosis with imiquimod.
2001 Dec
Imiquimod for plantar and periungual warts.
2001 Dec
[Anal condyloma: its management is still difficult].
2001 Oct
Topical immunomodulators--progress towards treating inflammation, infection, and cancer.
2001 Oct
Treatment of human papilloma virus in a 6-month-old infant with imiquimod 5% cream.
2001 Sep-Oct
Imiquimod 5% cream in the treatment of human papillomavirus-16-positive erythroplasia of Queyrat.
2002
New treatment modalities for basal cell carcinoma.
2002
Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment.
2002
Viral diseases of the skin: diagnosis and antiviral treatment.
2002
[Perspectives for the treatment and prevention of herpes simplex infections].
2002 Apr
Human papillomavirus: a review.
2002 Apr
Gateways to Clinical Trials.
2002 Apr
Clinical inquiries. What is the most effective treatment for external genital warts?
2002 Apr
Treatment of a large superficial basal cell carcinoma with 5% imiquimod: a case report and review of the literature.
2002 Apr
Imiquimod and genital herpes.
2002 Apr
The effects of 5% imiquimod cream on high-grade vulval intraepithelial neoplasia.
2002 Apr
Squamous cell carcinoma in situ of the penis successfully treated with imiquimod 5% cream.
2002 Apr
To cut a long story short - the use of imiquimod in resistant warts.
2002 Apr
Treatment of high-grade vaginal intraepithelial neoplasia with imiquimod cream.
2002 Aug 1
[Pharma clinics. Medication of the month. Imiquimod (Aldara): an immunomodulator for the skin].
2002 Feb
Porokeratosis of Mibelli: successful treatment with 5% imiquimod cream.
2002 Feb
Increased frequency of dosing of imiquimod 5% cream in the treatment of external genital warts in women.
2002 Feb
Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway.
2002 Feb
Experimental nonsurgical tattoo removal in a guinea pig model with topical imiquimod and tretinoin.
2002 Jan
Imiquimod 5% cream is an acceptable treatment option for external anogenital warts in uncircumcised males.
2002 Jan
Imiquimod and HIV transmission.
2002 Jan
Recent advances in dermatology.
2002 Jan
The importance of patient and healthcare provider perceptions in the evaluation of imiquimod and other prior treatments for anogenital warts.
2002 Jan
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
Successful treatment of anogenital Bowen's disease with the immunomodulator imiquimod, and monitoring of therapy by DNA image cytometry.
2002 Jul
Imiquimod: a potential role in dermatology?
2002 Jul
Efficacy of imiquimod on external anogenital warts in HIV-infected patients previously treated by highly active antiretroviral therapy.
2002 Jul 5
Treatment of non-genital warts with topical imiquimod 5% cream.
2002 Jul-Aug
Gateways to Clinical Trials. June 2002.
2002 Jun
Therapeutic response of a brother and sister with xeroderma pigmentosum to imiquimod 5% cream.
2002 Jun
New treatments for actinic keratoses.
2002 Jun 24
Treatment of recalcitrant plantar warts with imiquimod.
2002 Mar
Immunomodulation as a treatment strategy for genital herpes: review of the evidence.
2002 Mar
Treatment of Bowen's disease of the penis with imiquimod.
2002 Mar
Gateways to clinical trials.
2002 May
Imiquimod: a new immune response modifier for the treatment of external genital warts and other diseases in dermatology.
2002 May
Imiquimod stimulates innate and cell mediated immunity which controls virus infections and tumors.
2002 May
Imiquimod 5% cream: a new treatment option for basal cell carcinoma.
2002 May
Imiquimod in the treatment of actinic keratoses and other intraepithelial neoplasms.
2002 May
Imiquimod 5% cream: a topical immune response modifier.
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

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
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
Name Type Language
IMIQUIMOD
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
IMIQUIMOD [USP-RS]
Common Name English
ALDARA
Brand Name English
NSC-759651
Code English
IMIQUIMOD [USP MONOGRAPH]
Common Name English
S-26308
Code English
IMIQUIMOD [WHO-DD]
Common Name English
IMIQUIMOD [EMA EPAR]
Common Name English
ZYCLARA
Brand Name English
IMIQUIMOD [VANDF]
Common Name English
4-AMINO-1-ISOBUTYL-1H-IMIDAZO(4,5-C)QUINOLINE
Systematic Name English
S26308
Code English
IMIQUIMOD [INN]
Common Name English
IMIQUIMOD [MI]
Common Name English
1H-IMIDAZO(4,5-C)QUINOLIN-4-AMINE, 1-(2-METHYLPROPYL)-
Systematic Name English
IMIQUIMOD [ORANGE BOOK]
Common Name English
R-837
Code English
NSC-369100
Code English
IMIQUIMOD [MART.]
Common Name English
IMIQUIMOD [JAN]
Common Name English
IMIQUIMOD [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000009267
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
WHO-VATC QD06BB10
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
WHO-ATC D06BB10
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
FDA ORPHAN DRUG 425314
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
NCI_THESAURUS C129820
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
NDF-RT N0000009267
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
NDF-RT N0000009269
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
NDF-RT N0000000157
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
EMA ASSESSMENT REPORTS ALDARA (AUTHORIZED: CONDYLOMATA ACUMINATA)
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
NDF-RT N0000009269
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
FDA ORPHAN DRUG 707519
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
EMA ASSESSMENT REPORTS ZARTRA (WITHDRAWN: CONDYLOMATA ACUMINATA)
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
Code System Code Type Description
INN
6911
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
MESH
C056493
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
MERCK INDEX
M6234
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY Merck Index
PUBCHEM
57469
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
PRIMARY
IUPHAR
5003
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
USP_CATALOG
1338313
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
PRIMARY USP-RS
ChEMBL
CHEMBL1282
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
DRUG CENTRAL
1429
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
CAS
99011-02-6
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
WIKIPEDIA
IMIQUIMOD
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
PRIMARY
EPA CompTox
99011-02-6
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
DRUG BANK
DB00724
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
FDA UNII
P1QW714R7M
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
RXCUI
59943
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
PRIMARY RxNorm
HSDB
8129
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
NCI_THESAURUS
C1431
Created by admin on Fri Jun 25 22:11:48 UTC 2021 , Edited by admin on Fri Jun 25 22:11:48 UTC 2021
PRIMARY
EVMPD
SUB12453MIG
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY
LACTMED
Imiquimod
Created by admin on Fri Jun 25 22:11:47 UTC 2021 , Edited by admin on Fri Jun 25 22:11:47 UTC 2021
PRIMARY