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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:29 UTC
HMDB IDHMDB0014862
Secondary Accession Numbers
  • HMDB14862
Metabolite Identification
Common NameImiquimod
DescriptionImiquimod, also known as R 837 or aldara, 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. Imiquimod is a drug which 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. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod is a very strong basic compound (based on its pKa). In humans, imiquimod is involved in toll-like receptor pathway 2. It is not used on warts inside the vagina, penis, or rectum. 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.
Structure
Data?1582753229
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 Weight240.3036
Monoisotopic Molecular Weight240.137496532
IUPAC Name1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
Traditional Nameimiquimod
CAS Registry Number99011-02-6
SMILES
CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N
InChI Identifier
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)
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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point292 - 294 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.25 g/LNot Available
LogP2.7Not 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c04-3940000000-1662afa92a44e20e76baSpectrum
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
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00724 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00724 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00724
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID51809
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImiquimod
METLIN IDNot Available
PubChem Compound57469
PDB IDNot Available
ChEBI ID36704
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:10411278 ]
  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. [PubMed:11812998 ]
  3. Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. [PubMed:14616337 ]
  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. [PubMed:17343595 ]
  5. 3M [Link]

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]