clobetasone (CED0012707)

Record Information
Version1.0
Creation Date2016-06-03 11:03:48 UTC
Update Date2026-08-21 22:25:13 UTC
Accession NumberCHEM043569
Identification
Common Nameclobetasone
ClassSmall Molecule
Description
Clobetasone is an organic compound with the formula C22H26ClFO4 and an average molecular weight of 408.89 g/mol. It clobetasone belongs to the pregnane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This compound is found in or released from three recorded sources, including corticosteroids, antiinflammatory agents, and antiinflammatory agents and antiinfectives in combination, all of which are categorized under healthcare, pharmaceuticals & veterinary products. The recorded exposure route for clobetasone is topical. Regarding its biological activity, clobetasone acts as an agonist of the glucocorticoid receptor (NR3C1), which is its sole recorded protein target.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC22H26ClFO4
Average Molecular Mass408.890 g/mol
Monoisotopic Mass408.150 g/mol
CAS Registry Number54063-32-0
IUPAC Name(1R,2S,10S,11S,13S,14R,15S)-14-(2-chloroacetyl)-1-fluoro-14-hydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione
Traditional Name(1R,2S,10S,11S,13S,14R,15S)-14-(2-chloroacetyl)-1-fluoro-14-hydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione
SMILES[H][C@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)C(=O)C[C@]2(C)[C@@]1(O)C(=O)CCl
InChI IdentifierInChI=1S/C22H26ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-16,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19-,20-,21-,22-/m0/s1
InChI KeyXXIFVOHLGBURIG-OZCCCYNHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 9-halo-steroid
  • Halo-steroid
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • Delta-1,4-steroid
  • Alpha-haloketone
  • Alpha-chloroketone
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Alkyl halide
  • Alkyl fluoride
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP2.88ALOGPS
logP3.6ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.72 m³·mol⁻¹ChemAxon
Polarizability41.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a59-0009400000-58aa14385529e1abf2f8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0059200000-fc33391a9b8be9408948Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-0495000000-4f7d506995b096664526Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0004900000-48584aeb526210da8cc5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-2009300000-90d69ba011193e8fb7a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0hfy-1029000000-607597c9dd522f435754Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1262.0Log mg/kg[710:2200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
309CorticosteroidsHealthcare, pharmaceuticals & veterinary productsNot Available
396Antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
397Antiinflammatory agents and antiinfectives in combinationHealthcare, pharmaceuticals & veterinary productsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Clobetasone Action Pathway
Clobetasone Action Pathway
Clobetasone Drug Metabolism Action Pathway
Clobetasone Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)3.19182
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)4.98235
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)1.79053
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.155698
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)1.86838
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)44.2184
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)0.233548
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)13.2344
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.155698
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)14.0129
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)8.32987
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)43.1285
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)117.708
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)889.038
Protein kinase C epsilon type structureClick to view 3D structureProtein kinase C epsilon typeQ02156HumansPredicted (SEA)265.232
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)275.586
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)192.755
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)164.885
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)1174.51
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)1314.64
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)1293.0
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)22.8098
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)2577.59
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)1510.66
Phospholipase A2, membrane associated structureClick to view 3D structurePhospholipase A2, membrane associatedP14555HumansPredicted (SEA)41.9607
Concentrations
Not Available
External Links
DrugBank IDDB13158
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkClobetasone
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References