IMIQUIMOD

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H16N4
Molecular Weight	240.3036
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2N

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

Molecular Formula	C14H16N4
Molecular Weight	240.3036
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
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	Potency
SK-MEL-2 1 Target ID: CHEMBL614917 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24966637	Inhibitor 8297
Interleukin-8 3 Target ID: CHEMBL2157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22128302	Activator 1430	16.9 µM [EC50]
Interleukin-10 2 Target ID: P22301 Gene ID: 3586.0 Gene Symbol: IL10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22128302	Activator 1430	17.0 µM [EC50]
Toll-like receptor 7 12 Target ID: CHEMBL5936 Sources: http://www.drugbank.ca/drugs/DB00724	Agonist 2678	2.12 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Actinic keratosis 11 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	Primary	Approved 8429	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 1997
Primary superficial basal cell carcinoma 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	Primary	Approved 8429	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 1997
External genital and perianal warts/condyloma acuminata 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	Primary	Approved 8429	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 1997

C_max

Value	Dose	Co-administered	Analyte	Population
120 ng/mL REVIEW https://www.ema.europa.eu/en/documents/scientific-discussion/aldara-epar-scientific-discussion_en.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/scientific-discussion/aldara-epar-scientific-discussion_en.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.7 h REVIEW https://www.ema.europa.eu/en/documents/scientific-discussion/aldara-epar-scientific-discussion_en.pdf	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: https://pubmed.ncbi.nlm.nih.gov/10597781 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: https://pubmed.ncbi.nlm.nih.gov/10597781 Page: p.2400	Disc. AE: Localised skin reaction... AEs leading to discontinuation/dose reduction: Localised skin reaction (1.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/10597781 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: https://pubmed.ncbi.nlm.nih.gov/10597781 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: https://pubmed.ncbi.nlm.nih.gov/10597781 Page: p.2400

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:36704	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:36704
ChemicalBook	CB2664655	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2664655
ChemicalBook	CB9257146	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9257146
MolPort	MolPort-002-507-845	https://www.molport.com/shop/molecule-link/MolPort-002-507-845
Selleck Chemicals	Imiquimod	http://www.selleckchem.com/products/Imiquimod.html
ZINC	ZINC000019632912	http://zinc15.docking.org/substances/ZINC000019632912
eMolecules	1935723	https://www.emolecules.com/cgi-bin/more?vid=1935723

PubMed

Title	Date	PubMed
Treatment of external genital warts in men using 5% imiquimod cream applied three times a week, once daily, twice daily, or three times a day.	2001 Apr	11318254
Immune booster used to fight drug-resistant herpes.	2001 Aug	11590979
Imiquimod for plantar and periungual warts.	2001 Dec	11775772
Imiquimod and resiquimod as novel immunomodulators.	2001 Dec	11733457
Successful treatment of drug-resistant cutaneous leishmaniasis in humans by use of imiquimod, an immunomodulator.	2001 Dec 1	11692295
Imiquimod and 5% fluorouracil therapy for anal and perianal squamous cell carcinoma in situ in an HIV-1-positive man.	2001 Jan	11176654
Fighting infection using immunomodulatory agents.	2001 Jul	11727500
Treatment of immune-mediated skin diseases: future perspectives.	2001 Jul-Aug	11399542
Difficult wart cases -- use of imiquimod cream 5%.	2001 Jun	11368824
Imiquimod applied topically: A novel immune response modifier.	2001 Mar	11298484
Dermal dendritic cells in anogenital warty lesions unresponsive to an immune-response modifier.	2001 Mar	11168764
Daily or weekly therapy with resiquimod (R-848) reduces genital recurrences in herpes simplex virus-infected guinea pigs during and after treatment.	2001 Mar 15	11237799
Contact dermatitis from topical antiviral drugs.	2001 May	11298689
Imiquimod 5% cream is a safe and effective self-applied treatment for anogenital warts--results of an open-label, multicentre Phase IIIB trial.	2001 Nov	11589811
Gateways to Clinical Trials.	2002 Apr	12087878
'Rub on' treatment for basal-cell carcinoma.	2002 Apr	12067676
Clinical inquiries. What is the most effective treatment for external genital warts?	2002 Apr	11978251
Treatment of high-grade vaginal intraepithelial neoplasia with imiquimod cream.	2002 Aug 1	12151484
[Pharma clinics. Medication of the month. Imiquimod (Aldara): an immunomodulator for the skin].	2002 Feb	11942177
The importance of patient and healthcare provider perceptions in the evaluation of imiquimod and other prior treatments for anogenital warts.	2002 Jan	11802927
Topical imiquimod 5% cream in the treatment of Bowen's disease of the penis.	2002 Jan	11756968
The epidemiology and treatment of anogenital warts in Singapore: a retrospective evaluation.	2002 Jul	12161888
Gateways to Clinical Trials. June 2002.	2002 Jun	12168506
Therapeutic response of a brother and sister with xeroderma pigmentosum to imiquimod 5% cream.	2002 Jun	12081683
Imiquimod 5% cream in the treatment of anogenital warts in female patients.	2002 Jun	12065134
Infectious diseases. 6: Sexually transmitted infections: new diagnostic approaches and treatments.	2002 Jun 3	12064989
Gateways to clinical trials.	2002 May	12092009
Treatment of vulvar intraepithelial neoplasia 2/3 with imiquimod.	2002 May	12063878
Successful treatment of multiple superficial basal cell carcinomas with topical imiquimod: case report and review of the literature.	2002 May	12030878
Efficacy of imiquimod 5% cream in the treatment of recalcitrant warts in children.	2002 May-Jun	12047649
Safety studies of topical imiquimod 5% cream on normal skin exposed to ultraviolet radiation.	2002 Sep 2	12160622

Patents

Sample Use Guides

In Vivo Use Guide

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

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:16:01 GMT 2023` Edited by `admin` on `Sat Dec 16 05:16:01 GMT 2023`
Record UNII	P1QW714R7M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IMIQUIMOD

Official Name

English

IMIQUIMOD [USP-RS]

Common Name

English

ALDARA

Brand Name

English

Imiquimod [WHO-DD]

Common Name

English

TMX-101

Code

English

NSC-759651

Code

English

IMIQUIMOD [USP MONOGRAPH]

Common Name

English

S-26308

Code

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