<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:28:13 UTC</creation_date>
  <update_date>2026-08-22 03:48:17 UTC</update_date>
  <accession/>
  <common_name>Fluocinolone acetonide</common_name>
  <class>SmallMolecule</class>
  <description>Fluocinolone acetonide (C24H30F2O6) is a chemical compound with an average molecular weight of 452.49 g/mol. Fluocinolone acetonide belongs to the hydroxysteroids, a subclass of steroids and steroid derivatives within the organic compounds.

The compound is found in or released from 31 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized in antiinflammatory agents, vasoprotectives, and corticosteroids, including corticosteroid combinations with antibiotics and antiseptics. Other recorded sources include food preservation in food, food processing and cookware; household cleaning and consumer products such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices; and electrical and electronic equipment, including antennas, amplifiers, communication cables or conductors, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for this compound include oral, topical, auricular, inhalation, intraocular, and intravitreal.

Fluocinolone acetonide interacts with seven recorded protein targets. It acts as an agonist, inducer, or inhibitor of the glucocorticoid receptor (NR3C1), as well as Annexin A1 (ANXA1), Annexin A2 (ANXA2), Annexin A3 (ANXA3), and three other proteins.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one</synonym>
  </synonyms>
  <chemical_formula>C24H30F2O6</chemical_formula>
  <average_molecular_weight>452.4882</average_molecular_weight>
  <monisotopic_moleculate_weight>452.201045102</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one</iupac_name>
  <traditional_iupac>capex</traditional_iupac>
  <cas_registry_number>67-73-2</cas_registry_number>
  <smiles>[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO</smiles>
  <inchi>InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1</inchi>
  <inchikey>FEBLZLNTKCEFIT-VSXGLTOVSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternate_parents>
      <alternative_parent>1,3-dioxolanes</alternative_parent>
      <alternative_parent>11-beta-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>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Halogenated steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketals</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organofluorides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-1,4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>6-halo-steroid</substituent>
      <substituent>9-halo-steroid</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic 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>Ketal</substituent>
      <substituent>Ketone</substituent>
      <substituent>Meta-dioxolane</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organofluoride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>11beta-hydroxy steroid</descriptor>
      <descriptor>20-oxo steroid</descriptor>
      <descriptor>21-hydroxy steroid</descriptor>
      <descriptor>3-oxo-Delta(1),Delta(4)-steroid</descriptor>
      <descriptor>cyclic ketal</descriptor>
      <descriptor>fluorinated steroid</descriptor>
      <descriptor>glucocorticoid</descriptor>
      <descriptor>organic heteropentacyclic compound</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Fluocinolone acetonide Action Pathway</name>
      <smpdb_id>SMP0126241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fluocinolone acetonide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143039</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.6</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.47e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>452.4882</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>452.201045102</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H30F2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FEBLZLNTKCEFIT-VSXGLTOVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>93.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>111.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</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:0x00007f7244c1ae68&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00591</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6215</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5980</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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</compound>
