<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:10:17 UTC</creation_date>
  <update_date>2026-05-14 16:52:11 UTC</update_date>
  <accession/>
  <common_name>Rimexolone</common_name>
  <class>SmallMolecule</class>
  <description>Rimexolone is an organic compound with the formula C23H32O4 and an average molecular weight of 372.50 g/mol. Rimexolone belongs to the androstane steroids, a subclass of steroids and steroid derivatives within the organic compounds.

This compound is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically as an antiinflammatory agent and corticosteroid. Its recorded route of exposure is ophthalmic. Rimexolone acts on two recorded protein targets, serving as an agonist/modulator of the glucocorticoid receptor (NR3C1) and the steroid hormone receptor ERR1 (ESRRA).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C23H32O4</chemical_formula>
  <average_molecular_weight>372.505</average_molecular_weight>
  <monisotopic_moleculate_weight>372.23005951</monisotopic_moleculate_weight>
  <iupac_name>methyl (1S,2R,10S,11S,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate</iupac_name>
  <traditional_iupac>rimexolone</traditional_iupac>
  <cas_registry_number>49697-38-3</cas_registry_number>
  <smiles>[H][C@@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]2(C)[C@@]1(C)C(=O)OC</smiles>
  <inchi>InChI=1S/C23H32O4/c1-13-10-17-16-7-6-14-11-15(24)8-9-21(14,2)19(16)18(25)12-22(17,3)23(13,4)20(26)27-5/h8-9,11,13,16-19,25H,6-7,10,12H2,1-5H3/t13-,16+,17+,18+,19-,21+,22+,23-/m1/s1</inchi>
  <inchikey>HJPMTDNGLRNDJA-ZVXCBTRXSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxo delta-1,4-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Delta-1,4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl esters</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-1,4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Delta-1,4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl ester</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Rimexolone Action Pathway</name>
      <smpdb_id>SMP0126253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rimexolone Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143330</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>4.38</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.73e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl (1S,2R,10S,11S,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>372.505</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>372.23005951</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]2(C)[C@@]1(C)C(=O)OC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H32O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H32O4/c1-13-10-17-16-7-6-14-11-15(24)8-9-21(14,2)19(16)18(25)12-22(17,3)23(13,4)20(26)27-5/h8-9,11,13,16-19,25H,6-7,10,12H2,1-5H3/t13-,16+,17+,18+,19-,21+,22+,23-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HJPMTDNGLRNDJA-ZVXCBTRXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>105.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.96</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:0x00007f726775a6f8&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00896</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>39507</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>36120</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
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    <target>
      <target_id>BE0000794</target_id>
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    <target>
      <target_id>BE0003722</target_id>
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  </targets>
</compound>
