Beclazone (CHEM019955)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:39:17 UTC
Update Date2016-11-09 01:16:06 UTC
Accession NumberCHEM019955
Identification
Common NameBeclazone
ClassSmall Molecule
DescriptionA steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(11beta,16beta)-9-Chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dioneChEBI
9-Chloro-11beta-hydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionateChEBI
9-Chloro-16beta-methyl-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionateChEBI
AerobecChEBI
AldecinChEBI
AnceronChEBI
AndionChEBI
BeclacinChEBI
BecloforteChEBI
BeclometChEBI
Beclometasone 17,21-dipropionateChEBI
BeclorhinolChEBI
BeclovalChEBI
BecloventChEBI
BecodisksChEBI
BeconaseChEBI
BeconasolChEBI
BecotideChEBI
Clenil-aChEBI
EntydermaChEBI
InaloneChEBI
KorbutoneChEBI
PropadermChEBI
Rino-clenilChEBI
SanasthmaxChEBI
SanasthmylChEBI
VancenaseChEBI
VancerilChEBI
ViarexChEBI
ViaroxChEBI
QnaslKegg
(11b,16b)-9-Chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dioneGenerator
(11Β,16β)-9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dioneGenerator
9-Chloro-11b-hydroxy-16b-methylpregna-1,4-diene-3,20-dione 17,21-dipropionateGenerator
9-Chloro-11b-hydroxy-16b-methylpregna-1,4-diene-3,20-dione 17,21-dipropionic acidGenerator
9-Chloro-11beta-hydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionic acidGenerator
9-Chloro-11β-hydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionateGenerator
9-Chloro-11β-hydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionic acidGenerator
9-Chloro-16b-methyl-11b,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionateGenerator
9-Chloro-16b-methyl-11b,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionic acidGenerator
9-Chloro-16beta-methyl-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionic acidGenerator
9-Chloro-16β-methyl-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionateGenerator
9-Chloro-16β-methyl-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionic acidGenerator
Beclometasone 17,21-dipropionic acidGenerator
Beclometasone dipropionic acidGenerator
Beclomethasone dipropionateHMDB
3m Brand OF beclomethasone dipropionateHMDB
Asche brand OF beclomethasone dipropionateHMDB
Asmabec clickhalerHMDB
BeclocortHMDB
Medeva brand OF beclomethasone dipropionateHMDB
Orion brand OF beclomethasone dipropionateHMDB
AeroBec forteHMDB
Allen and hanburys brand OF beclomethasone dipropionateHMDB
Apotex brand OF beclomethasone dipropionateHMDB
AscocortonylHMDB
BeclametHMDB
Beclo azuHMDB
BecloturmantHMDB
FilairHMDB
Norton brand OF beclomethasone dipropionateHMDB
ProlairHMDB
Schering-plough brand OF beclomethasone dipropionateHMDB
Aldo brand OF beclomethasone dipropionateHMDB
Azupharma brand OF beclomethasone dipropionateHMDB
Beclo asmaHMDB
BeclometasoneHMDB
BeclomethasoneHMDB
Beconase aqHMDB
Dipropionate, beclomethasoneHMDB
Filair forteHMDB
Fujisawa brand OF beclomethasone dipropionateHMDB
Glaxo wellcome brand OF beclomethasone dipropionateHMDB
GlaxoSmithKline brand 1 OF beclomethasone dipropionateHMDB
GlaxoSmithKline brand 3 OF beclomethasone dipropionateHMDB
JunikHMDB
Nasobec aqueousHMDB
RespocortHMDB
Shire brand OF beclomethasone dipropionateHMDB
BecodiskHMDB
QvarHMDB
Schering brand 1 OF beclomethasone dipropionateHMDB
United drug brand OF beclomethasone dipropionateHMDB
a And H brand OF beclomethasone dipropionateHMDB
Apo-beclomethasoneHMDB
BeclazoneHMDB
Beclazone easy breatheHMDB
Bemedrex easyhalerHMDB
BronchocortHMDB
Celltech brand OF beclomethasone dipropionateHMDB
EcobecHMDB
GlaxoSmithKline brand 2 OF beclomethasone dipropionateHMDB
Ivax brand OF beclomethasone dipropionateHMDB
Schering brand 2 OF beclomethasone dipropionateHMDB
VentolairHMDB
ViarinHMDB
Beclomethasone dipropionic acidHMDB
Beclometasone dipropionateChEBI
Chemical FormulaC28H37ClO7
Average Molecular Mass521.042 g/mol
Monoisotopic Mass520.223 g/mol
CAS Registry Number5534-09-8
IUPAC Name2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-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 Namebeconase
SMILES[H][C@@]12C[C@H](C)[C@](OC(=O)CC)(C(=O)COC(=O)CC)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=1S/C28H37ClO7/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 KeyKUVIULQEHSCUHY-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
  • Chlorohydrin
  • Cyclic ketone
  • Secondary alcohol
  • Halohydrin
  • Ketone
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl chloride
  • 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 Solubility0.0021 g/LALOGPS
logP3.69ALOGPS
logP4.43ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity134.79 m³·mol⁻¹ChemAxon
Polarizability54.41 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00pi-7931200000-ebf9cfbf75bf09c67c7aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0bvi-9427050000-eb3614d4b3688b88c0c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000f-0930000000-081eac0a05abab8fc5faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000f-0930000000-081eac0a05abab8fc5faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-3920000000-d6e2b1ac89621299e6bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0536-0000390000-d1146b326a2bf27937e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0489240000-9581961e5dddfb7a403fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0h71-3892000000-454fb634c4339a1ebfe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kmj-4001960000-2444d4d01b60622dc9daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9016710000-03228f1ad114124f50a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-7259300000-8a403afc0efa6ee4f110Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0600-9000440000-d5250fc13ae4ff60aa89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9001300000-fb71d87f62527dae4806Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9002000000-182d2c80d6e083b565f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009730000-81e60ed81d61c6314c37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01xx-0009200000-d06a88f89fcfe1e37e3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9627500000-178854364472c3c4dd81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9006200000-345f47155712cbf26442Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9003000000-fa1ac5e3b880b5467f13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-89a0f1c5a6da8df63c3cSpectrum
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 IDDB00394
HMDB IDHMDB0014538
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBeclometasone_dipropionate
Chemspider ID20396
ChEBI ID3002
PubChem Compound ID21700
Kegg Compound IDC07813
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12938103
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16920559
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18694371
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19747642
5. Willey RF, Milne LJ, Crompton GK, Grant IW: Beclomethasone dipropionate aerosol and oropharyngeal candidiasis. Br J Dis Chest. 1976 Jan;70(1):32-8.
6. Salzman GA, Pyszczynski DR: Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber. J Allergy Clin Immunol. 1988 Feb;81(2):424-8.
7. Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, Kohno S: Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone. Ann Allergy Asthma Immunol. 2003 Jun;90(6):646-51.
8. Castilla C, Perez-Simon JA, Sanchez-Guijo FM, Diez-Campelo M, Ocio E, Perez-Persona E, Lopez-Villar O, Vazquez L, Caballero D, San Miguel JF: Oral beclomethasone dipropionate for the treatment of gastrointestinal acute graft-versus-host disease (GVHD). Biol Blood Marrow Transplant. 2006 Sep;12(9):936-41.
9. Hockenbery DM, Cruickshank S, Rodell TC, Gooley T, Schuening F, Rowley S, David D, Brunvand M, Berryman B, Abhyankar S, Bouvier M, McDonald GB: A randomized, placebo-controlled trial of oral beclomethasone dipropionate as a prednisone-sparing therapy for gastrointestinal graft-versus-host disease. Blood. 2007 May 15;109(10):4557-63. Epub 2007 Jan 23.
10. Astegiano M, Pagano N, Sapone N, Simondi D, Bertolusso L, Bresso F, Demarchi B, Pellicano R, Bonardi R, Marconi S, Rizzetto M: Efficacy and safety of oral beclomethasone dipropionate for ileal or ileal-right colon Crohn's disease of mild-to-moderate activity or in remission: Retrospective study. Biomed Pharmacother. 2007 Jul;61(6):370-6. Epub 2007 Mar 12.
11. McDonald GB: Oral beclomethasone dipropionate: a topically active corticosteroid for the treatment of gastrointestinal graft-versus-host disease following allogeneic hematopoietic cell transplantation. Expert Opin Investig Drugs. 2007 Oct;16(10):1709-24.
12. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
13. 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.
14. 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.
15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
16. FDA label.
17. The lipid handbook with CD-ROM