Imiquimod (CHEM017634)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:30:20 UTC
Update Date2016-11-09 01:15:38 UTC
Accession NumberCHEM017634
Identification
Common NameImiquimod
ClassSmall Molecule
DescriptionImiquimod 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c04-3940000000-1662afa92a44e20e76baSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000f-2970000000-08cb009f804dd3b43f69Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-2910000000-58faefee0903c8967370Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2090000000-6f9d6e2f4d7747ae95dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9580000000-d31c7988dbae6085a29dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9400000000-503227ffe338b6a8d185Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0390000000-44a8c5b2ac2cd485d2f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0940000000-5f1b9952a672997a0b4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-d71208eb00e043d7e84fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0390000000-d88591b18aaba14469cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-0690000000-71a9a845a947ea2d2862Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05as-0910000000-a9b321d2938173c4f73fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7474f6fc851ae052786cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-d514bde35ff30a0c785cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0910000000-946992964c1e54432a88Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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