Identification
- Summary
Imiquimod is a toll-like receptor 7 agonist used to treat non hyperkeratotic, non hypertrophic actinic keratosis, basal cell carcinoma, genital or perianal warts, and condyloma acuminata.
- Brand Names
- Aldara, Vyloma, Zyclara
- Generic Name
- Imiquimod
- DrugBank Accession Number
- DB00724
- Background
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. Miquimod is also used to treat a skin condition of the face and scalp called actinic keratoses and certain types of skin cancer called superficial basal cell carcinoma.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Imiquimod (DB00724)
- Weight
- Average: 240.3036
Monoisotopic: 240.137496532 - Chemical Formula
- C14H16N4
- Synonyms
- 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
- 4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline
- Imiquimod
- Imiquimodum
- External IDs
- R 837
- R-837
- S 26308
- S26308
Pharmacology
- Indication
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Actinic keratoses of the face •••••••••••• Treatment of Actinic keratoses of the scalp •••••••••••• Treatment of Condyloma acuminata •••••••••••• Management of Hsv infection ••• ••••• Treatment of Molluscum contagiosum ••• ••••• - Contraindications & Blackbox Warnings
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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.
- Mechanism of action
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.
Target Actions Organism AToll-like receptor 7 agonistHumans UToll-like receptor 8 agonistHumans - Absorption
Well absorbed through skin (as a cream)
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
20 hours (topical dose), 2 hours (subcutaneous dose)
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include flu-like symptoms, such as fever, fatigue, headache, nausea, diarrhoea and muscle pain.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Imiquimod can be increased when it is combined with Abametapir. Allogeneic processed thymus tissue The therapeutic efficacy of Allogeneic processed thymus tissue can be decreased when used in combination with Imiquimod. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Imiquimod. Apalutamide The serum concentration of Imiquimod can be decreased when it is combined with Apalutamide. Avanafil The serum concentration of Avanafil can be increased when it is combined with Imiquimod. - Food Interactions
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Beselna (Mochida) / Imimore (Panalab) / Imiquad (Glenmark) / Labimiq (ITF - Labomed) / Li Di (Mingxin Pharmaceutical) / Miquimod (Lazar) / Nan Bo (Topfond Pharmaceutical) / Nilwart (Dr. Reddy's) / Omiquidar (Darier) / Tian Rui (Yangtze River Pharma) / Vetland (Landsteiner) / You Care (Nang Kuang) / Youbiqing (The United Laboratories Ltd)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aldara Cream 5 %(w/w) Cutaneous Viatris Healthcare Limited 2016-09-20 Not applicable EU 
Aldara Cream 50 mg/1000mg Topical Physicians Total Care, Inc. 2003-06-19 2009-09-30 US 
Aldara Cream 50 mg/1000mg Topical 3 M Pharmaceuticals 2011-06-24 2015-01-31 US Aldara Cream 5 %(w/w) Cutaneous Viatris Healthcare Limited 2016-09-20 Not applicable EU Aldara Cream 50 mg/1g Topical Bausch Health US LLC 1997-02-27 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-imiquimod Cream 5 % w/w Topical Apotex Corporation 2013-12-31 Not applicable Canada 
Imiquimod Cream 37.5 mg/1g Topical Teva Pharmaceuticals USA, Inc. 2020-07-30 Not applicable US Imiquimod Cream 50 mg/1g Topical Glenmark Pharmaceuticals Inc., USA 2012-03-06 Not applicable US Imiquimod Cream 50 mg/1g Topical Impax Generics 2011-02-28 2017-06-01 US Imiquimod Cream 50 mg/1g Topical Teva 2013-12-19 2015-04-30 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Niacinamide 2% Imiquimod (5 g/100g) + Levocetirizine dihydrochloride (1 g/100g) + Nicotinamide (2 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Tretinoin 0.05% Imiquimod (5 g/100g) + Levocetirizine dihydrochloride (1 g/100g) + Tretinoin (0.05 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Imiquimod 5% / Niacinamide 4% Imiquimod (5 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-07 Not applicable US Imiquimod 5% / Salicylic Acid 30% / Tretinoin 0.1% Imiquimod (5 g/100g) + Salicylic acid (30 g/100g) + Tretinoin (0.1 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-07 Not applicable US Imiquimod 5% / Tretinoin 0.025% Imiquimod (5 g/100g) + Tretinoin (0.025 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-07 Not applicable US
Categories
- ATC Codes
- D06BB10 — Imiquimod
- Drug Categories
- Adjuvants, Immunologic
- Aminoquinolines
- Antineoplastic Agents
- Cancer immunotherapy
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Heterocyclic Compounds, Fused-Ring
- Immune Response Modifiers
- Immunologic Factors
- Immunomodulatory Agents
- Immunosuppressive Agents
- Immunotherapy
- Increased Cytokine Activity
- Increased Cytokine Production
- Interferon Inducers
- Misc. Skin and Mucous Membrane Agents
- Quinolines
- Toll-Like Receptor Agonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as imidazoquinolines. These are aromatic heterocyclic compounds containing an imidazole ring fused to a quinoline ring system. In some configurations, the imidazole ring shares a nitrogen atom with the quinoline moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Imidazoquinolines
- Direct Parent
- Imidazoquinolines
- Alternative Parents
- Aminoquinolines and derivatives / Imidazo-[4,5-c]pyridines / Aminopyridines and derivatives / N-substituted imidazoles / Imidolactams / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds show 1 more
- Substituents
- Amine / Aminopyridine / Aminoquinoline / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Imidazo-[4,5-c]pyridine show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- imidazoquinoline (CHEBI:36704)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- P1QW714R7M
- CAS number
- 99011-02-6
- InChI Key
- DOUYETYNHWVLEO-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
- SMILES
- CC(C)CN1C=NC2=C1C1=C(C=CC=C1)N=C2N
References
- Synthesis Reference
- US4689338
- General References
- van Egmond S, Hoedemaker C, Sinclair R: Successful treatment of perianal Bowen's disease with imiquimod. Int J Dermatol. 2007 Mar;46(3):318-9. [Article]
- Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S: Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol. 2002 Feb;3(2):196-200. Epub 2002 Jan 22. [Article]
- Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. [Article]
- Miller RL, Gerster JF, Owens ML, Slade HB, Tomai MA: Imiquimod applied topically: a novel immune response modifier and new class of drug. Int J Immunopharmacol. 1999 Jan;21(1):1-14. [Article]
- External Links
- Human Metabolome Database
- HMDB0014862
- KEGG Drug
- D02500
- PubChem Compound
- 57469
- PubChem Substance
- 46505394
- ChemSpider
- 51809
- BindingDB
- 50240849
- 59943
- ChEBI
- 36704
- ChEMBL
- CHEMBL1282
- ZINC
- ZINC000019632912
- Therapeutic Targets Database
- DAP000278
- PharmGKB
- PA449972
- PDBe Ligand
- 6T0
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Imiquimod
- PDB Entries
- 5lbt / 5zsf
- FDA label
- Download (144 KB)
- MSDS
- Download (36.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Alopecia Areata (AA) 1 4 Completed Treatment Actinic Cheilitis 1 4 Completed Treatment Actinic Keratosis (AK) 5 4 Completed Treatment Actinic Keratosis (AK) / Keratosis 1 4 Completed Treatment Alopecia Areata (AA) 1
Pharmacoeconomics
- Manufacturers
- Graceway pharmaceuticals llc
- Nycomed us inc
- Graceway Pharmaceuticals, LLC
- Packagers
- 3M Health Care
- Dispensing Solutions
- E. Fougera and Co.
- Graceway Pharmaceuticals
- Dosage Forms
Form Route Strength Cream Cutaneous 5 %(w/w) Cream Topical 50 mg/1000mg Cream Topical 5 %w/w Cream Topical 5 % Cream Topical 9.375 mg Cream Topical 5 g Cream Topical 375000 g Cream Topical 50 mg/g Cream Topical 12.5 mg Cream Topical Cream Topical 12.5 mg/0.25g Cream Topical 5 % w/w Cream Topical 50 mg/1g Gel Topical Cream Cutaneous 5 % Cream Cutaneous 12.500 mg Capsule, liquid filled Topical 12.5 mg Cream Topical 50.00 mg Cream Topical 12.500 mg Cream Topical 250 mg/250mg Cream Topical 500000 g Cream Topical 3.75 g Cream Topical 3.75 % w/w Cream Cutaneous 3.75 %(w/w) Cream Topical 2.5 mg/1g Cream Topical 2.5 mg/100mg Cream Topical 2.5 % w/w Cream Topical 3.75 % Cream Topical 3.75 mg/100mg Cream Topical 37.5 mg/1g - Prices
Unit description Cost Unit Aldara 5% Cream Pack 46.99USD pack Imiquimod 5% Cream Packet 42.89USD packet Imiquimod 5% cream 33.17USD each Aldara 5% cream 26.04USD each Zyclara 3.75% cream 24.43USD each DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US4689338 No 1987-08-25 2009-08-25 US US7696159 Yes 2010-04-13 2024-10-01 US US8222270 No 2012-07-17 2029-12-11 US US8236816 No 2012-08-07 2029-12-11 US US8299109 No 2012-10-30 2029-12-11 US US8598196 No 2013-12-03 2029-08-18 US US10238645 No 2019-03-26 2029-08-18 US US10238644 No 2019-03-26 2029-12-11 US US10918635 No 2021-02-16 2030-04-30 US US11202752 No 2021-12-21 2030-04-30 US US11318130 No 2009-12-11 2029-12-11 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 292-294 °C Not Available water solubility Poorly soluble Not Available logP 2.7 Not Available - Predicted Properties
Property Value Source Water Solubility 0.247 mg/mL ALOGPS logP 2.83 ALOGPS logP 2.65 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 19.99 Chemaxon pKa (Strongest Basic) 5.01 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 56.73 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 72.54 m3·mol-1 Chemaxon Polarizability 26.67 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9967 Blood Brain Barrier + 0.955 Caco-2 permeable + 0.5995 P-glycoprotein substrate Non-substrate 0.5137 P-glycoprotein inhibitor I Non-inhibitor 0.8797 P-glycoprotein inhibitor II Inhibitor 0.6949 Renal organic cation transporter Non-inhibitor 0.5928 CYP450 2C9 substrate Non-substrate 0.8625 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.51 CYP450 1A2 substrate Inhibitor 0.8751 CYP450 2C9 inhibitor Non-inhibitor 0.8182 CYP450 2D6 inhibitor Inhibitor 0.7628 CYP450 2C19 inhibitor Non-inhibitor 0.634 CYP450 3A4 inhibitor Non-inhibitor 0.5131 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6829 Ames test AMES toxic 0.8884 Carcinogenicity Non-carcinogens 0.8917 Biodegradation Not ready biodegradable 0.9916 Rat acute toxicity 2.5683 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9546 hERG inhibition (predictor II) Inhibitor 0.5422
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.9076874 predictedDarkChem Lite v0.1.0 [M-H]- 163.0081874 predictedDarkChem Lite v0.1.0 [M-H]- 147.74078 predictedDeepCCS 1.0 (2019) [M+H]+ 162.1928874 predictedDarkChem Lite v0.1.0 [M+H]+ 163.0996874 predictedDarkChem Lite v0.1.0 [M+H]+ 150.0988 predictedDeepCCS 1.0 (2019) [M+Na]+ 163.0149874 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.26485 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR7 i...
- Gene Name
- TLR7
- Uniprot ID
- Q9NYK1
- Uniprot Name
- Toll-like receptor 7
- Molecular Weight
- 120920.8 Da
References
- Gibson SJ, Lindh JM, Riter TR, Gleason RM, Rogers LM, Fuller AE, Oesterich JL, Gorden KB, Qiu X, McKane SW, Noelle RJ, Miller RL, Kedl RM, Fitzgerald-Bocarsly P, Tomai MA, Vasilakos JP: Plasmacytoid dendritic cells produce cytokines and mature in response to the TLR7 agonists, imiquimod and resiquimod. Cell Immunol. 2002 Jul-Aug;218(1-2):74-86. [Article]
- Akira S, Hemmi H: Recognition of pathogen-associated molecular patterns by TLR family. Immunol Lett. 2003 Jan 22;85(2):85-95. [Article]
- Dummer R, Urosevic M, Kempf W, Hoek K, Hafner J, Burg G: Imiquimod in basal cell carcinoma: how does it work? Br J Dermatol. 2003 Nov;149 Suppl 66:57-8. [Article]
- Otero M, Calarota SA, Felber B, Laddy D, Pavlakis G, Boyer JD, Weiner DB: Resiquimod is a modest adjuvant for HIV-1 gag-based genetic immunization in a mouse model. Vaccine. 2004 Apr 16;22(13-14):1782-90. [Article]
- Ambach A, Bonnekoh B, Nguyen M, Schon MP, Gollnick H: Imiquimod, a Toll-like receptor-7 agonist, induces perforin in cytotoxic T lymphocytes in vitro. Mol Immunol. 2004 Apr;40(18):1307-14. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Single-stranded rna binding
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. Acts v...
- Gene Name
- TLR8
- Uniprot ID
- Q9NR97
- Uniprot Name
- Toll-like receptor 8
- Molecular Weight
- 119826.82 Da
References
- Dummer R, Urosevic M, Kempf W, Hoek K, Hafner J, Burg G: Imiquimod in basal cell carcinoma: how does it work? Br J Dermatol. 2003 Nov;149 Suppl 66:57-8. [Article]
- Zhu J, Lai K, Brownile R, Babiuk LA, Mutwiri GK: Porcine TLR8 and TLR7 are both activated by a selective TLR7 ligand, imiquimod. Mol Immunol. 2008 Jun;45(11):3238-43. doi: 10.1016/j.molimm.2008.02.028. Epub 2008 Apr 24. [Article]
- Gorden KB, Gorski KS, Gibson SJ, Kedl RM, Kieper WC, Qiu X, Tomai MA, Alkan SS, Vasilakos JP: Synthetic TLR agonists reveal functional differences between human TLR7 and TLR8. J Immunol. 2005 Feb 1;174(3):1259-68. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55