<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:37:47 UTC</creation_date>
  <update_date>2026-05-14 16:38:58 UTC</update_date>
  <accession/>
  <common_name>Betamethasone</common_name>
  <class>SmallMolecule</class>
  <description>Betamethasone is an organic compound with the formula C22H29FO5 and an average molecular weight of 392.46 g/mol. Betamethasone belongs to the hydroxysteroids, a subclass of steroids and steroid derivatives within the organic compounds. In terms of biological activity, it functions as an agonist of the Glucocorticoid receptor (NR3C1).

The compound is found in or released from 13 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, these sources include corticosteroids, intestinal antiinflammatory agents, vasoprotectives, and corticosteroids in combination with antibiotics or antiseptics, among six others. Additionally, it is associated with electrical and electronic equipment, specifically amplifiers and antennas.

Betamethasone is associated with a wide variety of recorded exposure routes. These include oral, rectal, and topical applications, as well as auricular, ophthalmic, and cutaneous routes. Injectable routes of exposure include intravenous, intravascular, intramuscular, intradermal, and intralesional administration. Specialized delivery methods include infiltration, intraspinal, intrathecal, epidural, perineural, intra-articular, intrabursal, and soft tissue administration.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</synonym>
  </synonyms>
  <chemical_formula>C22H29FO5</chemical_formula>
  <average_molecular_weight>392.4611</average_molecular_weight>
  <monisotopic_moleculate_weight>392.199902243</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one</iupac_name>
  <traditional_iupac>betamethasone</traditional_iupac>
  <cas_registry_number>378-44-9</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C</smiles>
  <inchi>InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1</inchi>
  <inchikey>UREBDLICKHMUKA-DVTGEIKXSA-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>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>Gluco/mineralocorticoids, progestogins and derivatives</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>Primary alcohols</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>21-hydroxysteroid</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>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>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</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>21-hydroxy 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/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.68</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.05e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-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>392.4611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.199902243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C22H29FO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UREBDLICKHMUKA-DVTGEIKXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>102.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</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:0x00007f726e49ad30&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00443</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>9782</pubchem_compound_id>
  <chembl_id/>
  <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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      <target_id>BE0000794</target_id>
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  </targets>
</compound>
