Clobetasol propionate (CHEM018637)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:24:47 UTC
Update Date2016-11-09 01:15:50 UTC
Accession NumberCHEM018637
Identification
Common NameClobetasol propionate
ClassSmall Molecule
DescriptionClobetasol propionate is a prednisolone derivative with higher specificity for glucocorticoid receptors than mineralocorticoid receptors.[L11815] It has demonstrated superior activity compared to [fluocinonide][A190963] and was first described in the literature in 1974.[A190936] Clobetasol Propionate was granted FDA approval on 27 December 1985.[L11809]
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
21-Chloro-9-fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-propionateChEBI
Clobetasol 17-propanoateChEBI
Clobetasol 17-propionateChEBI
ClobexKegg
CormaxKegg
OluxKegg
21-Chloro-9-fluoro-11b,17-dihydroxy-16b-methylpregna-1,4-diene-3,20-dione 17-propionateGenerator
21-Chloro-9-fluoro-11b,17-dihydroxy-16b-methylpregna-1,4-diene-3,20-dione 17-propionic acidGenerator
21-Chloro-9-fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-propionic acidGenerator
21-Chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-propionateGenerator
21-Chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-propionic acidGenerator
Clobetasol 17-propanoic acidGenerator
Clobetasol 17-propionic acidGenerator
Clobetasol propionic acidGenerator
Embeline eMeSH
Clobetasol 17 propionateMeSH
ClofenazonMeSH
EmbelineMeSH
TemovateMeSH
ClobetasolMeSH
DermovateMeSH
Chemical FormulaC25H32ClFO5
Average Molecular Mass466.970 g/mol
Monoisotopic Mass466.192 g/mol
CAS Registry Number25122-46-7
IUPAC Name(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl propanoate
Traditional Nametemovate
SMILES[H][C@@]12C[C@H](C)[C@](OC(=O)CC)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
InChI KeyCBGUOGMQLZIXBE-XGQKBEPLSA-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
  • Steroid ester
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 9-halo-steroid
  • Halo-steroid
  • Hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Alpha-haloketone
  • Alpha-chloroketone
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclic ketone
  • Fluorohydrin
  • Secondary alcohol
  • Halohydrin
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alkyl halide
  • Organofluoride
  • Alkyl chloride
  • Organochloride
  • Alkyl fluoride
  • Organohalogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0041 g/LALOGPS
logP3.49ALOGPS
logP4.18ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)13.63ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.32 m³·mol⁻¹ChemAxon
Polarizability48.28 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05fr-1920000000-defac8a82087405b74dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a6r-0596000000-b19d97ac39952d18b68eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03mj-3971000000-8f42562c23aaf5e5d240Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066s-3003900000-de1fe5b252dd99c47da6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9036600000-8d6e9893a1d817fa1237Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-4298100000-9d10026ac5aee897f91fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2002900000-3d0b3c5111e9b7289d57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-5009800000-c98c0202af4a862421a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-8009000000-66051bd53af18b72b922Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01013
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 LinkClobetasol
Chemspider IDNot Available
ChEBI ID31414
PubChem Compound ID32798
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available