Betamethasone dipropionate (CHEM016588)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:37:52 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016588
Identification
Common NameBetamethasone dipropionate
ClassSmall Molecule
DescriptionA steroid ester that is betamethasone in which the hydroxy hydrogens at positions 17 and 21 are replaced by propanoyl groups. It is used in combination with calcipotriene hydrate, a synthetic vitamin D analogue, for the topical treatment of plaque psoriasis in adult patients.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
9-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione-17,21-dipropionateChEBI
Betamethasone 17,21-dipropionateChEBI
DiproleneKegg
Rinderon-DPKegg
SernivoKegg
9-Fluoro-11b,17,21-trihydroxy-16b-methylpregna-1,4-diene-3,20-dione-17,21-dipropionateGenerator
9-Fluoro-11b,17,21-trihydroxy-16b-methylpregna-1,4-diene-3,20-dione-17,21-dipropionic acidGenerator
9-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione-17,21-dipropionic acidGenerator
9-Fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione-17,21-dipropionateGenerator
9-Fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione-17,21-dipropionic acidGenerator
Betamethasone 17,21-dipropionic acidGenerator
Betamethasone dipropionic acidGenerator
DiprosoneMeSH
MaxivateMeSH
BelodermMeSH
Betamethasone propionateMeSH
Augmented betamethasone dipropionateMeSH
Betamethasone-17,21-dipropionateMeSH
[2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-Hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoic acidGenerator
Betamethasone dipropionateMeSH
Chemical FormulaC28H37FO7
Average Molecular Mass504.595 g/mol
Monoisotopic Mass504.252 g/mol
CAS Registry Number5593-20-4
IUPAC Name2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
Traditional Namebetamethasone dipropionate
SMILES[H][C@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@]([H])(O)C[C@]2(C)[C@@]1(OC(=O)CC)C(=O)COC(=O)CC
InChI IdentifierInChI=1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
InChI KeyCIWBQSYVNNPZIQ-XYWKZLDCSA-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
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Alkyl halide
  • 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 Solubility0.0046 g/LALOGPS
logP3.38ALOGPS
logP3.96ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)13.64ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.05 m³·mol⁻¹ChemAxon
Polarizability53.16 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3001920000-b114bedb6a5885037a8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9036800000-e3ea6110f35df1197970Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5295200000-1b0c71bc637f901a37beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kmi-9001430000-6c2b5bf24bd63411cf00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9002200000-9bdf77748ba9c6a54552Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9002000000-e4440018ef395e025bb2Spectrum
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 IDDBSALT000851
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 LinkBetamethasone_Dipropionate
Chemspider IDNot Available
ChEBI ID31276
PubChem Compound ID21800
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23621170
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24533503
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24593129
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24684739
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24684740
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24980277
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25279474
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25307472
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25355140
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25410121
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25412565
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=25556056
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25566573
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25607705
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=26094549
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=26444907
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=26659941