Imiquimod (CED0002280)

Record Information
Version1.0
Creation Date2016-05-22 04:30:20 UTC
Update Date2026-08-19 06:02:54 UTC
Accession NumberCHEM017634
Identification
Common NameImiquimod
ClassSmall Molecule
Description
Imiquimod is an organic compound with the formula C14H16N4 and an average molecular weight of 240.30 g/mol. Imiquimod belongs to the imidazoquinolines, a subclass of quinolines and derivatives within the organic compounds. Biologically, it functions as an agonist (PMC6331894, PMC8197201). It acts as an agonist of two recorded protein targets: Toll-like receptor 7 (TLR7) and Toll-like receptor 8 (TLR8). In medical applications, imiquimod is used as a treatment for basal cell carcinoma (PMC9266369) and skin cancer (PMC8197201). Additionally, it is associated with psoriasis (PMC12028938). Within the category of healthcare, pharmaceuticals, and veterinary products, it is classified as a chemotherapeutic. The compound is found in or released from ten recorded sources. These include household cleaning and consumer products such as non-electric simulated smoking devices, cigar cigarettes, and other smoking requisites. It is also found in electrical and electronic equipment, including television systems, video games, antennas, line transmission systems, and electrically stimulated smoking devices. Further sources include indoor air, dust, and atmospheric transport. Recorded exposure routes for the compound include topical application and inhalation.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-amineChEBI
4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinolineChEBI
ImiquimodumChEBI
R 837ChEBI
AldaraKegg
ZyclaraKegg
Imiquimod acetateHMDB
1-Isobutyl-1H-imidazo(4,5-c)quinolin-4-amineHMDB
Chemical FormulaC14H16N4
Average Molecular Mass240.304 g/mol
Monoisotopic Mass240.137 g/mol
CAS Registry Number99011-02-6
IUPAC Name1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
Traditional Nameimiquimod
SMILESCC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N
InChI IdentifierInChI=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)
InChI KeyDOUYETYNHWVLEO-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassImidazoquinolines
Direct ParentImidazoquinolines
Alternative Parents
Substituents
  • Imidazoquinoline
  • Aminoquinoline
  • Imidazopyridine
  • Imidazo-[4,5-c]pyridine
  • Aminopyridine
  • N-substituted imidazole
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Azacycle
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.83ALOGPS
logP2.65ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area56.73 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity72.54 m³·mol⁻¹ChemAxon
Polarizability26.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0c04-3940000000-1662afa92a44e20e76baNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000f-2970000000-08cb009f804dd3b43f69Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-2910000000-58faefee0903c8967370Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2090000000-6f9d6e2f4d7747ae95dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9580000000-d31c7988dbae6085a29dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9400000000-503227ffe338b6a8d185Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0390000000-44a8c5b2ac2cd485d2f2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0940000000-5f1b9952a672997a0b4eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-d71208eb00e043d7e84fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0390000000-d88591b18aaba14469cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-0690000000-71a9a845a947ea2d2862Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05as-0910000000-a9b321d2938173c4f73fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-7474f6fc851ae052786cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-d514bde35ff30a0c785cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0910000000-946992964c1e54432a88Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
265.0Log mg/kg[150:470]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
psoriasisassociated_withNot AvailablePMC12028938
skin canceris_treatment_forNot AvailablePMC8197201
basal cell carcinomais_treatment_forNot AvailablePMC9266369
skin squamous cell carcinomais_treatment_forNot AvailablePMC12310484
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
233BrushesPersonal care & cosmeticsNot Available
307ChemotherapeuticsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
604Pest AttractantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Toll-Like Receptor Pathway 2
Toll-Like Receptor Pathway 2
Imiquimod Drug Metabolism Action Pathway
Imiquimod Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureButyrylcholinesteraseQ9JKC1Rattus norvegicusPredicted (SEA)97.5451
Click to view 3D structureButyrylcholinesteraseQ9N1N9Equus caballusPredicted (SEA)118.097
Click to view 3D structureAcetylcholinesteraseP23795Bos taurusPredicted (SEA)75.2802
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)466.005
Cyclin-dependent kinase 5 structureClick to view 3D structureCyclin-dependent kinase 5Q00535HumansPredicted (SEA)2410.52
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)47.4102
Toll-like receptor 7 structureClick to view 3D structureToll-like receptor 7Q9NYK1HumansPredicted (SEA)15.0249
Oxidized purine nucleoside triphosphate hydrolase structureClick to view 3D structureOxidized purine nucleoside triphosphate hydrolaseP36639HumansPredicted (SEA)0.0778492
Histamine H2 receptor structureClick to view 3D structureHistamine H2 receptorP25021HumansPredicted (SEA)34.8764
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)47.4102
Alpha-1-antichymotrypsin structureClick to view 3D structureAlpha-1-antichymotrypsinP01011HumansPredicted (SEA)0.856341
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)593.367
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)380.683
Click to view 3D structureAcetylcholinesteraseP37136Rattus norvegicusPredicted (SEA)173.759
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)471.299
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)165.819
Click to view 3D structureBifunctional dihydrofolate reductase-thymidylate synthaseQ07422Toxoplasma gondiiPredicted (SEA)73.4897
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)517.23
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP16184Pneumocystis cariniiPredicted (SEA)53.6381
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)539.884
Click to view 3D structureCytochrome P450 2B11P24460Canis lupus familiarisPredicted (SEA)5.99439
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)713.021
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)341.525
Click to view 3D structureDihydrofolate reductaseQ920D2Rattus norvegicusPredicted (SEA)72.5555
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)2713.59
Concentrations
Not Available
External Links
DrugBank IDDB00724
HMDB IDHMDB0014862
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkImiquimod
Chemspider ID51809
ChEBI ID36704
PubChem Compound ID57469
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
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.
3. Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8.
4. 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.
5. 3M: http://www.3m.com/us/healthcare/pharma/aldara/con_overview.jhtml
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=10861101
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15868314
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16217984
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18424373
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27548435
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=28872561
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=29422777
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29485187
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=29505317
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=29596875