<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 06:16:13 UTC</creation_date>
  <update_date>2026-08-21 22:47:54 UTC</update_date>
  <accession/>
  <common_name>Fluorometholone</common_name>
  <class>SmallMolecule</class>
  <description>Fluorometholone is an organic compound with the chemical formula C22H29FO4 and an average molecular weight of 376.46 g/mol. Fluorometholone belongs to the pregnane steroids, a subclass of steroids and steroid derivatives within the organic compounds.

This compound acts as an agonist of the Glucocorticoid receptor (NR3C1). It has been recorded in 30 different sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized in corticosteroids, corticosteroids combined with antibiotics, anti-acne preparations, antiinflammatory agents, and vasoprotectives. It is also associated with household cleaning and consumer products, including tobacco smoke filters, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in food, food processing, and cookware contexts, specifically in the preparation of vinegar, the preparation of wine or sparkling wine, food preservation, and fermentation processes for beer. Other recorded sources include electrical and electronic equipment, such as antennas, amplifiers, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, and electric hearing aids. The recorded exposure route for this compound is ophthalmic.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</synonym>
  </synonyms>
  <chemical_formula>C22H29FO4</chemical_formula>
  <average_molecular_weight>376.4617</average_molecular_weight>
  <monisotopic_moleculate_weight>376.204987621</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</iupac_name>
  <traditional_iupac>fluorometholone</traditional_iupac>
  <cas_registry_number>426-13-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C</smiles>
  <inchi>InChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1</inchi>
  <inchikey>FAOZLTXFLGPHNG-KNAQIMQKSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-1,4-steroids</alternative_parent>
      <alternative_parent>Alkyl fluorides</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</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>Fluorohydrins</alternative_parent>
      <alternative_parent>Halogenated steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organofluorides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-oxo-delta-1,4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>9-halo-steroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl fluoride</substituent>
      <substituent>Alkyl halide</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Delta-1,4-steroid</substituent>
      <substituent>Fluorohydrin</substituent>
      <substituent>Halo-steroid</substituent>
      <substituent>Halohydrin</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organofluoride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>11beta-hydroxy steroid</descriptor>
      <descriptor>17alpha-hydroxy steroid</descriptor>
      <descriptor>20-oxo steroid</descriptor>
      <descriptor>3-oxo-Delta(1),Delta(4)-steroid</descriptor>
      <descriptor>fluorinated steroid</descriptor>
      <descriptor>glucocorticoid</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Fluorometholone Action Pathway</name>
      <smpdb_id>SMP0126255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fluorometholone Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fluorometholone Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174582</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.42</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.66e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>376.4617</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>376.204987621</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C22H29FO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FAOZLTXFLGPHNG-KNAQIMQKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>100.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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:0x00007f727a2051e0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00324</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>9878</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>9494</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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  </targets>
</compound>
