Imiquimod

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofActinic keratoses of the face••••••••••••
Treatment ofActinic keratoses of the scalp••••••••••••
Treatment ofCondyloma acuminata••••••••••••
Management ofHsv infection••• •••••
Treatment ofMolluscum contagiosum••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
AToll-like receptor 7
agonist
Humans
UToll-like receptor 8
agonist
Humans
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
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Toxicity

Symptoms of overdose include flu-like symptoms, such as fever, fatigue, headache, nausea, diarrhoea and muscle pain.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Imiquimod can be increased when it is combined with Abametapir.
Allogeneic processed thymus tissueThe therapeutic efficacy of Allogeneic processed thymus tissue can be decreased when used in combination with Imiquimod.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Imiquimod.
ApalutamideThe serum concentration of Imiquimod can be decreased when it is combined with Apalutamide.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Imiquimod.
Food Interactions
  • Take with or without food.

Products

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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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AldaraCream5 %(w/w)CutaneousViatris Healthcare Limited2016-09-20Not applicableEU flag
AldaraCream50 mg/1000mgTopicalPhysicians Total Care, Inc.2003-06-192009-09-30US flag
AldaraCream5 %(w/w)CutaneousViatris Healthcare Limited2016-09-20Not applicableEU flag
AldaraCream50 mg/1000mgTopical3 M Pharmaceuticals2011-06-242015-01-31US flag
AldaraCream50 mg/1000mgTopicalGraceway Pharmaceuticals2011-06-242015-01-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-imiquimodCream5 % w/wTopicalApotex Corporation2013-12-31Not applicableCanada flag
ImiquimodCream50 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2011-04-15Not applicableUS flag
ImiquimodCream50 mg/1gTopicalPhysicians Total Care, Inc.2010-09-22Not applicableUS flag
ImiquimodCream37.5 mg/1gTopicalTeva Pharmaceuticals USA, Inc.2020-07-30Not applicableUS flag
ImiquimodCream50 mg/1gTopicalGlenmark Pharmaceuticals Inc., USA2012-03-06Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Niacinamide 2%Imiquimod (5 g/100g) + Levocetirizine dihydrochloride (1 g/100g) + Nicotinamide (2 g/100g)GelTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Tretinoin 0.05%Imiquimod (5 g/100g) + Levocetirizine dihydrochloride (1 g/100g) + Tretinoin (0.05 g/100g)GelTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
Imiquimod 5% / Niacinamide 4%Imiquimod (5 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2019-05-07Not applicableUS flag
Imiquimod 5% / Salicylic Acid 30% / Tretinoin 0.1%Imiquimod (5 g/100g) + Salicylic acid (30 g/100g) + Tretinoin (0.1 g/100g)GelTopicalSincerus Florida, LLC2019-05-07Not applicableUS flag
Imiquimod 5% / Tretinoin 0.025%Imiquimod (5 g/100g) + Tretinoin (0.025 g/100g)GelTopicalSincerus Florida, LLC2019-05-07Not applicableUS flag

Categories

ATC Codes
D06BB10 — Imiquimod
Drug Categories
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
  1. 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]
  2. 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]
  3. Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. [Article]
  4. 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]
Human Metabolome Database
HMDB0014862
KEGG Drug
D02500
PubChem Compound
57469
PubChem Substance
46505394
ChemSpider
51809
BindingDB
50240849
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAlopecia Areata (AA)1
4CompletedTreatmentActinic Cheilitis1
4CompletedTreatmentActinic Keratosis (AK)5
4CompletedTreatmentActinic Keratosis (AK) / Keratosis1
4CompletedTreatmentAlopecia 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
FormRouteStrength
CreamCutaneous5 %(w/w)
CreamTopical50 mg/1000mg
CreamTopical5 %w/w
CreamTopical5 %
CreamTopical9.375 mg
CreamTopical5 g
CreamTopical375000 g
CreamTopical50 mg/g
CreamTopical12.5 mg
CreamTopical
CreamTopical12.5 mg/0.25g
CreamTopical5 % w/w
CreamTopical50 mg/1g
GelTopical
CreamCutaneous5 %
CreamCutaneous12.500 mg
Capsule, liquid filledTopical12.5 mg
CreamTopical50.00 mg
CreamTopical12.500 mg
CreamTopical250 mg/250mg
CreamTopical500000 g
CreamTopical3.75 g
CreamTopical3.75 % w/w
CreamCutaneous3.75 %(w/w)
CreamTopical2.5 mg/1g
CreamTopical2.5 mg/100mg
CreamTopical2.5 % w/w
CreamTopical3.75 %
CreamTopical3.75 mg/100mg
CreamTopical37.5 mg/1g
Prices
Unit descriptionCostUnit
Aldara 5% Cream Pack46.99USD pack
Imiquimod 5% Cream Packet42.89USD packet
Imiquimod 5% cream33.17USD each
Aldara 5% cream26.04USD each
Zyclara 3.75% cream24.43USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US4689338No1987-08-252009-08-25US flag
US7696159Yes2010-04-132024-10-01US flag
US8222270No2012-07-172029-12-11US flag
US8236816No2012-08-072029-12-11US flag
US8299109No2012-10-302029-12-11US flag
US8598196No2013-12-032029-08-18US flag
US10238645No2019-03-262029-08-18US flag
US10238644No2019-03-262029-12-11US flag
US10918635No2021-02-162030-04-30US flag
US11202752No2021-12-212030-04-30US flag
US11318130No2009-12-112029-12-11US flag
US11850245No2010-04-302030-04-30US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)292-294 °CNot Available
water solubilityPoorly solubleNot Available
logP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.247 mg/mLALOGPS
logP2.83ALOGPS
logP2.65Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)19.99Chemaxon
pKa (Strongest Basic)5.01Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area56.73 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity72.54 m3·mol-1Chemaxon
Polarizability26.67 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.955
Caco-2 permeable+0.5995
P-glycoprotein substrateNon-substrate0.5137
P-glycoprotein inhibitor INon-inhibitor0.8797
P-glycoprotein inhibitor IIInhibitor0.6949
Renal organic cation transporterNon-inhibitor0.5928
CYP450 2C9 substrateNon-substrate0.8625
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.51
CYP450 1A2 substrateInhibitor0.8751
CYP450 2C9 inhibitorNon-inhibitor0.8182
CYP450 2D6 inhibitorInhibitor0.7628
CYP450 2C19 inhibitorNon-inhibitor0.634
CYP450 3A4 inhibitorNon-inhibitor0.5131
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6829
Ames testAMES toxic0.8884
CarcinogenicityNon-carcinogens0.8917
BiodegradationNot ready biodegradable0.9916
Rat acute toxicity2.5683 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9546
hERG inhibition (predictor II)Inhibitor0.5422
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0c04-3940000000-1662afa92a44e20e76ba
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000f-2970000000-08cb009f804dd3b43f69
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-2910000000-58faefee0903c8967370
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-8520fa23a31e2879cb07
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0190000000-b869d5e4a9e3d5d96e97
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000f-0790000000-417893265e91d750aea7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dr-0190000000-c4af043a1174841b1c1a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0900000000-5169e81befc6ed18b9c7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-0900000000-36779114df6dc757f76e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-162.9076874
predicted
DarkChem Lite v0.1.0
[M-H]-163.0081874
predicted
DarkChem Lite v0.1.0
[M-H]-147.74078
predicted
DeepCCS 1.0 (2019)
[M+H]+162.1928874
predicted
DarkChem Lite v0.1.0
[M+H]+163.0996874
predicted
DarkChem Lite v0.1.0
[M+H]+150.0988
predicted
DeepCCS 1.0 (2019)
[M+Na]+163.0149874
predicted
DarkChem Lite v0.1.0
[M+Na]+156.26485
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Toll-like receptor 7
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
  1. 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]
  2. Akira S, Hemmi H: Recognition of pathogen-associated molecular patterns by TLR family. Immunol Lett. 2003 Jan 22;85(2):85-95. [Article]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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]
  2. 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]
  3. 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
  1. 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 March 18, 2024 16:48