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=C(C=CC=C3)N=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 8504
Interleukin-8 3 Target ID: CHEMBL2157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22128302	Activator 1447	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 1447	17.0 µM [EC50]
Toll-like receptor 7 13 Target ID: CHEMBL5936 Sources: http://www.drugbank.ca/drugs/DB00724	Agonist 2752	2.12 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Actinic keratosis 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020723s022lbl.pdf	Primary	Approved 8583	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 8583	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 8583	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
0.66 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
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

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
2.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11073288/	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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% OTHER GOV'T https://www.fda.gov/files/drugs/published/201153-Imiquimod-Clinpharm-PREA.pdf	multiple, topical		IMIQUIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

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	unhealthy, 35±6.9 Health Status: unhealthy Age Group: 35±6.9 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10597781	Disc. AE: Localised skin reaction... AEs leading to discontinuation/dose reduction: Localised skin reaction (1.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/10597781

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	unhealthy, 35±6.9 Health Status: unhealthy Age Group: 35±6.9 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10597781

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8/9 42 CYP2C19 2057 BSEP 550 MRP2 499 P-gp 1741 CYP1A1 132 MRP4 290 MRP3 246 UMAT 30	CYP1A1 389 CYP1A2 1197 CYP4F3B 7 CYP2J2 71 CYP1B1 104 CYP4F12 10 CYP2A6 626 CYP19A1 26 CYP2B6 776 CYP3A5 446 CYP2C19 1119 CYP2C8 810 CYP3A7 109 CYP4A11 137 P-gp 2052 CYP4F2 11 CYP2C18 149 CYP4F3A 3 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1347076#sid=865810	inconclusive [IC50 20.5962 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2007/P200700041/79000500_21900AMX01087_A100_2.pdf#page=28	likely
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2007/P200700041/79000500_21900AMX01087_A100_2.pdf#page=28 Page: 28.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2007/P200700041/79000500_21900AMX01087_A100_2.pdf#page=28 Page: 28.0	no
CYP2C8/9 42	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2007/P200700041/79000500_21900AMX01087_A100_2.pdf#page=28 Page: 28.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2007/P200700041/79000500_21900AMX01087_A100_2.pdf#page=28	no
UMAT 30	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/602162#sid=865810	no
CYP1A1 272	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	yes

Drug as victim

Target	Modality	Activity
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	likely
CYP19A1 26	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP2J2 71	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP3A7 109	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP4F12 10	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP4F2 11	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP4F3A 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP4F3B 7	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	no
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	yes
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31111189/	yes
P-gp 2052	substrate 4014 Sources: https://europepmc.org/article/ppr/ppr338675	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.pmda.go.jp/drugs/2007/P200700041/79000500_21900AMX01087_A100_2.pdf#page=21 Page: 21.0

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
eMolecules	1935723	https://www.emolecules.com/cgi-bin/more?vid=1935723
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

PubMed

Title	Date	PubMed
Safety studies of topical imiquimod 5% cream on normal skin exposed to ultraviolet radiation.	2002-09-02	12160622
Treatment of high-grade vaginal intraepithelial neoplasia with imiquimod cream.	2002-08-01	12151484
Efficacy of imiquimod on external anogenital warts in HIV-infected patients previously treated by highly active antiretroviral therapy.	2002-07-05	12131230
Treatment of non-genital warts with topical imiquimod 5% cream.	2002-07-04	12095879
The epidemiology and treatment of anogenital warts in Singapore: a retrospective evaluation.	2002-07	12161888
Successful treatment of anogenital Bowen's disease with the immunomodulator imiquimod, and monitoring of therapy by DNA image cytometry.	2002-07	12100202
Imiquimod: a potential role in dermatology?	2002-07	12100177
Infantile hemangioma: clinical resolution with 5% imiquimod cream.	2002-07	12071813
New treatments for actinic keratoses.	2002-06-24	12080275
Efficacy of imiquimod 5% cream in the treatment of recalcitrant warts in children.	2002-06-06	12047649
Infectious diseases. 6: Sexually transmitted infections: new diagnostic approaches and treatments.	2002-06-03	12064989
Gateways to Clinical Trials. June 2002.	2002-06	12168506
Therapeutic response of a brother and sister with xeroderma pigmentosum to imiquimod 5% cream.	2002-06	12081683
Imiquimod 5% cream in the treatment of anogenital warts in female patients.	2002-06	12065134
Gateways to clinical trials.	2002-05	12092009
Imiquimod: a new immune response modifier for the treatment of external genital warts and other diseases in dermatology.	2002-05	12087816
Imiquimod stimulates innate and cell mediated immunity which controls virus infections and tumors.	2002-05	12087815
Imiquimod 5% cream: a new treatment option for basal cell carcinoma.	2002-05	12087814
Imiquimod in the treatment of actinic keratoses and other intraepithelial neoplasms.	2002-05	12087813
Imiquimod 5% cream: a topical immune response modifier.	2002-05	12087812
Treatment of vulvar intraepithelial neoplasia 2/3 with imiquimod.	2002-05	12063878
Successful treatment of multiple superficial basal cell carcinomas with topical imiquimod: case report and review of the literature.	2002-05	12030878
Topical imiquimod cream 5% for resistant perianal warts in a renal transplant patient.	2002-05	11972940
[Perspectives for the treatment and prevention of herpes simplex infections].	2002-04	12122338
Human papillomavirus: a review.	2002-04	12120445
Gateways to Clinical Trials.	2002-04	12087878
'Rub on' treatment for basal-cell carcinoma.	2002-04	12067676
Clinical inquiries. What is the most effective treatment for external genital warts?	2002-04	11978251
Treatment of a large superficial basal cell carcinoma with 5% imiquimod: a case report and review of the literature.	2002-04	11966794
Imiquimod and genital herpes.	2002-04	11939822
The effects of 5% imiquimod cream on high-grade vulval intraepithelial neoplasia.	2002-04	11925122
Squamous cell carcinoma in situ of the penis successfully treated with imiquimod 5% cream.	2002-04	11907505
To cut a long story short - the use of imiquimod in resistant warts.	2002-04	11886616
Treatment of recalcitrant plantar warts with imiquimod.	2002-03	12006136
Immunomodulation as a treatment strategy for genital herpes: review of the evidence.	2002-03	11962724
Treatment of Bowen's disease of the penis with imiquimod.	2002-03	11862196
[Pharma clinics. Medication of the month. Imiquimod (Aldara): an immunomodulator for the skin].	2002-02	11942177
Porokeratosis of Mibelli: successful treatment with 5% imiquimod cream.	2002-02	11903259
Increased frequency of dosing of imiquimod 5% cream in the treatment of external genital warts in women.	2002-02	11818121
Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway.	2002-02	11812998
Experimental nonsurgical tattoo removal in a guinea pig model with topical imiquimod and tretinoin.	2002-01	11998793
Imiquimod 5% cream is an acceptable treatment option for external anogenital warts in uncircumcised males.	2002-01	11952292
Imiquimod and HIV transmission.	2002-01	11808542
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
Successful topical immunotherapy of bowenoid papulosis with imiquimod.	2001-12	11899127
[Anal condyloma: its management is still difficult].	2001-10	11894692
Topical immunomodulators--progress towards treating inflammation, infection, and cancer.	2001-10	11871495

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 `Mon Mar 31 21:28:22 GMT 2025` Edited by `admin` on `Mon Mar 31 21:28:22 GMT 2025`
Record UNII	P1QW714R7M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALDARA

Preferred Name

English

IMIQUIMOD

Official Name

English

IMIQUIMOD [USP-RS]

Common 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