IMIQUIMOD

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 Search

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
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 7701
Interleukin-8 3 Target ID: CHEMBL2157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22128302	Activator 1335	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 1335	17.0 µM [EC50]
Toll-like receptor 7 12 Target ID: CHEMBL5936 Sources: http://www.drugbank.ca/drugs/DB00724	Agonist 2456	2.12 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Actinic keratosis 9 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	Primary	Approved 7997	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 superficial basal cell carcinoma 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	Primary	Approved 7997	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
External genital and perianal warts/condyloma acuminata 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	Primary	Approved 7997	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

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
Topical imiquimod treatment of human papillomavirus in a patient with human immunodeficiency virus.	2001 Aug-Sep	11720183
Successful topical immunotherapy of bowenoid papulosis with imiquimod.	2001 Dec	11899127
Imiquimod and resiquimod as novel immunomodulators.	2001 Dec	11733457
Fighting infection using immunomodulatory agents.	2001 Jul	11727500
[Anal condyloma: its management is still difficult].	2001 Oct	11894692
Topical immunomodulators--progress towards treating inflammation, infection, and cancer.	2001 Oct	11871495
[Disseminated actinic keratoses. Comparison of topical photodynamic therapy with 5-aminolevulinic acid and topical 5% imiquimod cream].	2001 Oct	11715389
Treatment of human papilloma virus in a 6-month-old infant with imiquimod 5% cream.	2001 Sep-Oct	11737697
Treatment of anogenital warts in children with topical 0.05% podofilox gel and 5% imiquimod cream.	2001 Sep-Oct	11737696
Imiquimod 5% cream in the treatment of human papillomavirus-16-positive erythroplasia of Queyrat.	2002	12145439
New treatment modalities for basal cell carcinoma.	2002	12079222
Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment.	2002	12079221
Viral diseases of the skin: diagnosis and antiviral treatment.	2002	11817982
[Perspectives for the treatment and prevention of herpes simplex infections].	2002 Apr	12122338
Human papillomavirus: a review.	2002 Apr	12120445
'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 a large superficial basal cell carcinoma with 5% imiquimod: a case report and review of the literature.	2002 Apr	11966794
The effects of 5% imiquimod cream on high-grade vulval intraepithelial neoplasia.	2002 Apr	11925122
Squamous cell carcinoma in situ of the penis successfully treated with imiquimod 5% cream.	2002 Apr	11907505
To cut a long story short - the use of imiquimod in resistant warts.	2002 Apr	11886616
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
Porokeratosis of Mibelli: successful treatment with 5% imiquimod cream.	2002 Feb	11903259
Increased frequency of dosing of imiquimod 5% cream in the treatment of external genital warts in women.	2002 Feb	11818121
Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway.	2002 Feb	11812998
Experimental nonsurgical tattoo removal in a guinea pig model with topical imiquimod and tretinoin.	2002 Jan	11998793
Imiquimod 5% cream is an acceptable treatment option for external anogenital warts in uncircumcised males.	2002 Jan	11952292
Recent advances in dermatology.	2002 Jan	11806166
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
Successful treatment of anogenital Bowen's disease with the immunomodulator imiquimod, and monitoring of therapy by DNA image cytometry.	2002 Jul	12100202
Imiquimod: a potential role in dermatology?	2002 Jul	12100177
Infantile hemangioma: clinical resolution with 5% imiquimod cream.	2002 Jul	12071813
Efficacy of imiquimod on external anogenital warts in HIV-infected patients previously treated by highly active antiretroviral therapy.	2002 Jul 5	12131230
Treatment of non-genital warts with topical imiquimod 5% cream.	2002 Jul-Aug	12095879
Gateways to Clinical Trials. June 2002.	2002 Jun	12168506
Imiquimod 5% cream in the treatment of anogenital warts in female patients.	2002 Jun	12065134
New treatments for actinic keratoses.	2002 Jun 24	12080275
Infectious diseases. 6: Sexually transmitted infections: new diagnostic approaches and treatments.	2002 Jun 3	12064989
Immunomodulation as a treatment strategy for genital herpes: review of the evidence.	2002 Mar	11962724
Gateways to clinical trials.	2002 May	12092009
Imiquimod 5% cream: a new treatment option for basal cell carcinoma.	2002 May	12087814
Imiquimod 5% cream: a topical immune response modifier.	2002 May	12087812
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
Topical imiquimod cream 5% for resistant perianal warts in a renal transplant patient.	2002 May	11972940
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

Name

Type

Language

IMIQUIMOD

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

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PRIMARY

MERCK INDEX

M6234

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PRIMARY

Merck Index

PUBCHEM

57469

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PRIMARY

IUPHAR

5003

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PRIMARY

USP_CATALOG

1338313

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PRIMARY

USP-RS

ChEMBL

CHEMBL1282

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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

ACTIVE MOIETY


					P1QW714R7M

IMIQUIMOD

METABOLITE (PARENT)


					T8NPD94NTJ

R-842

Details

SMILES

InChI

DescriptionSources: http://www.drugbank.ca/drugs/DB00724Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/imiquimod.html

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2