<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:30:20 UTC</creation_date>
  <update_date>2026-08-19 06:02:54 UTC</update_date>
  <accession/>
  <common_name>Imiquimod</common_name>
  <class>SmallMolecule</class>
  <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.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C14H16N4</chemical_formula>
  <average_molecular_weight>240.3036</average_molecular_weight>
  <monisotopic_moleculate_weight>240.137496532</monisotopic_moleculate_weight>
  <iupac_name>1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine</iupac_name>
  <traditional_iupac>imiquimod</traditional_iupac>
  <cas_registry_number>99011-02-6</cas_registry_number>
  <smiles>CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N</smiles>
  <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)</inchi>
  <inchikey>DOUYETYNHWVLEO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Imidazoquinolines</sub_class>
    <direct_parent>Imidazoquinolines</direct_parent>
    <alternate_parents>
      <alternative_parent>Aminopyridines and derivatives</alternative_parent>
      <alternative_parent>Aminoquinolines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazo-[4,5-c]pyridines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminopyridine</substituent>
      <substituent>Aminoquinoline</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazo-[4,5-c]pyridine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyridine</substituent>
      <substituent>Imidazoquinoline</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>imidazoquinoline</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Toll-Like Receptor Pathway 2</name>
      <smpdb_id>SMP0069593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Imiquimod Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143168</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.65</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.47e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>240.3036</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>240.137496532</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H16N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DOUYETYNHWVLEO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>56.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3baeca5e68&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00724</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>57469</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>51809</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
