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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:52:26 UTC
HMDB IDHMDB0014687
Secondary Accession Numbers
  • HMDB14687
Metabolite Identification
Common NameDesoximetasone
DescriptionDesoximetasone is only found in individuals that have used or taken this drug. It is a topical anti-inflammatory glucocorticoid used in dermatoses, skin allergies, psoriasis, etc. [PubChem]The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. This is achieved first by the drug binding to the glucocorticoid receptors which then translocates into the nucleus and binds to DNA causing various activations and repressions of genes. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
Structure
Thumb
Synonyms
ValueSource
(11beta,16alpha)-9-fluoro-11,21-Dihydroxy-16-methylpregna-1,4-diene-3,20-dioneChEBI
9alpha-fluoro-16alpha-Methyl-Delta(1)-corticosteroneChEBI
DesoximetasonaChEBI
DesoximetasonumChEBI
DesoxymethasoneChEBI
(11b,16a)-9-fluoro-11,21-Dihydroxy-16-methylpregna-1,4-diene-3,20-dioneGenerator
(11β,16α)-9-fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dioneGenerator
9a-fluoro-16a-Methyl-delta(1)-corticosteroneGenerator
9α-fluoro-16α-methyl-δ(1)-corticosteroneGenerator
9a-fluoro-16a-Methyl-δ(1)-corticosteroneGenerator
DesoxiMeSH
Hoechst brand OF desoximetasoneMeSH
IbarilMeSH
Optipharma brand OF desoximetasoneMeSH
TopicorteMeSH
TopisolonMeSH
17-DesoxymethasoneMeSH
Abbott brand OF desoximetasoneMeSH
Medicis brand OF desoximetasoneMeSH
StiedexMeSH
17 DesoxymethasoneMeSH
DeoxydexamethasoneMeSH
Dermik brand OF desoximetasoneMeSH
Stiefel brand OF desoximetasoneMeSH
TopicortMeSH
Aventis brand OF desoximetasoneMeSH
Bipharma brand OF desoximetasoneMeSH
FlubasonMeSH
Chemical FormulaC22H29FO4
Average Molecular Weight376.4617
Monoisotopic Molecular Weight376.204987621
IUPAC Name(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Namedesoximetasone
CAS Registry Number382-67-2
SMILES
[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
InChI KeyVWVSBHGCDBMOOT-IIEHVVJPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • 20-oxosteroid
  • Pregnane-skeleton
  • 9-halo-steroid
  • Halo-steroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Halohydrin
  • Fluorohydrin
  • Cyclic ketone
  • Organic oxygen compound
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point217 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.031 g/LNot Available
LogP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP2.13ALOGPS
logP2.35ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.44ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.17 m³·mol⁻¹ChemAxon
Polarizability40.09 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05o0-0912000000-a19399cef0d27c3594e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-2943160000-a934ab87ed20665cae69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0859000000-a10700f328db7dc715b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-2940000000-d3344c1ae6eb70791755View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0859000000-a10700f328db7dc715b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-2940000000-d3344c1ae6eb70791755View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-d0e87553c50e0a0145c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6s-0109000000-07696481bbb48e48679fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kft-3498000000-c406362cf63dd705c638View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-518050b225f1b7caa912View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-1009000000-bb5c7b442c44ba33b8cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pba-4149000000-be3ea39b760207659651View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00547 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00547 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00547
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470604
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesoximetasone
METLIN IDNot Available
PubChem Compound5311067
PDB IDNot Available
ChEBI ID691037
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.