<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 06:34:23 UTC</creation_date>
  <update_date>2026-08-19 08:29:51 UTC</update_date>
  <accession/>
  <common_name>Luliconazole</common_name>
  <class>SmallMolecule</class>
  <description>Luliconazole is an organic compound with the formula C14H9Cl2N3S2 and an average molecular weight of 354.27 g/mol. Luliconazole belongs to the halobenzenes, a subclass of benzene and substituted derivatives within the organic compounds. It is used in healthcare, pharmaceuticals, and veterinary products as an antifungal for dermatological use, with topical application as the recorded exposure route. Mechanistically, it acts as an inhibitor of the protein target Lanosterol 14-alpha demethylase (ERG11).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C14H9Cl2N3S2</chemical_formula>
  <average_molecular_weight>354.27</average_molecular_weight>
  <monisotopic_moleculate_weight>352.961495</monisotopic_moleculate_weight>
  <iupac_name>2-[(2E,4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile</iupac_name>
  <traditional_iupac>luliconazole</traditional_iupac>
  <cas_registry_number>187164-19-8</cas_registry_number>
  <smiles>ClC1=CC(Cl)=C(C=C1)[C@@H]1CS\C(S1)=C(\C#N)N1C=CN=C1</smiles>
  <inchi>InChI=1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1</inchi>
  <inchikey>YTAOBBFIOAEMLL-REQDGWNSSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Halobenzenes</sub_class>
    <direct_parent>Dichlorobenzenes</direct_parent>
    <alternate_parents>
      <alternative_parent>1,3-dithiolanes</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Nitriles</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,3-dichlorobenzene</substituent>
      <substituent>1,3-dithiolane</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonitrile</substituent>
      <substituent>Dithiolane</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Nitrile</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>dichlorobenzene</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Luliconazole Action Pathway</name>
      <smpdb_id>SMP0125821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Luliconazole Drug Metabolism</name>
      <smpdb_id>SMP0130740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Luliconazole Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144227</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>4.07</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.59e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(2E,4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>354.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.961495</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>ClC1=CC(Cl)=C(C=C1)[C@@H]1CS\C(S1)=C(\C#N)N1C=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H9Cl2N3S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YTAOBBFIOAEMLL-REQDGWNSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>101</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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/>
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  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72248219a8&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB08933</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3003141</pubchem_compound_id>
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  <biocyc_id/>
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  <wikipidia/>
  <general_references/>
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</compound>
