<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:53:07 UTC</creation_date>
  <update_date>2026-08-21 18:38:08 UTC</update_date>
  <accession/>
  <common_name>Tazarotene</common_name>
  <class>SmallMolecule</class>
  <description>Tazarotene is an organic compound with the formula C21H21NO2S and an average molecular weight of 351.46 g/mol. Tazarotene belongs to the retinoids, a subclass of prenol lipids within the organic compounds. In industrial applications, it serves as a softener and conditioner. Within the healthcare and pharmaceutical sectors, it is utilized as an antipsoriatic.

The compound is found in or released from 19 recorded sources. These include electrical and electronic equipment, such as electrodes, hybrid capacitors, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. In the category of household cleaning and consumer products, it is associated with soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in building and construction materials, specifically floors, stairs and ramps, as well as in food processing and cookware related to food preservation and the preparation of vinegar. Recorded exposure routes for the compound include oral, topical, and cutaneous paths.

Tazarotene acts on four recorded protein targets, functioning as an agonist of Retinoic acid receptor alpha (RARA), Retinoic acid receptor beta (RARB), Retinoic acid receptor gamma (RARG), and Retinoic acid receptor RXR-beta (RXRB).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C21H21NO2S</chemical_formula>
  <average_molecular_weight>351.462</average_molecular_weight>
  <monisotopic_moleculate_weight>351.129299611</monisotopic_moleculate_weight>
  <iupac_name>ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate</iupac_name>
  <traditional_iupac>tazarotene</traditional_iupac>
  <cas_registry_number>118292-40-3</cas_registry_number>
  <smiles>CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1</smiles>
  <inchi>InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3</inchi>
  <inchikey>OGQICQVSFDPSEI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Retinoids</sub_class>
    <direct_parent>Retinoids</direct_parent>
    <alternate_parents>
      <alternative_parent>1-benzothiopyrans</alternative_parent>
      <alternative_parent>Alkylarylthioethers</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
      <alternative_parent>Thiochromanes</alternative_parent>
      <alternative_parent>Thiopyrans</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-benzothiopyran</substituent>
      <substituent>Alkylarylthioether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl thioether</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzothiopyran</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Tazarotene</substituent>
      <substituent>Thiochromane</substituent>
      <substituent>Thioether</substituent>
      <substituent>Thiopyran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>acetylenic compound</descriptor>
      <descriptor>ethyl ester</descriptor>
      <descriptor>pyridines</descriptor>
      <descriptor>retinoid</descriptor>
      <descriptor>thiochromane</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Tazarotene Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>5.22</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.50e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>351.462</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>351.129299611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H21NO2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OGQICQVSFDPSEI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>39.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</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/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72730bf148&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00799</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5381</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5188</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>
