Banner
Identification
Name Beclometasone dipropionate
Accession Number DB00394 (APRD00564)
Type small molecule
Groups approved
Description

Beclometasone dipropionate is a prodrug of the free form, beclometasone. An anti-inflammatory, synthetic glucocorticoid, it is used topically as an anti-inflammatory agent and in aerosol form for the treatment of asthma. Beclometasone dipropionate is also being investigated for oral treatment in mild-to-moderate Crohn’s disease of ileal or ileal-right colonic localisation and for “topical” use mild-to-moderate graft versus host disease.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Beclomethasone dipropionate
Salts Not Available
Brand names
Name Company
Aerobec
Aldecin
Anceron
Andion
Beclacin
Becloforte
Beclomet
Beclorhinol
Becloval
Beclovent
Becodisks
Beconase
Beconase AQ
Beconasol
Becotide
Clenil-A
Entyderma
Inalone
Korbutone
orBec DOR BioPharma, Inc.
Propaderm
QVAR
Rino-Clenil
Rivanase
Sanasthmax
Sanasthmyl
Vancenase
Vanceril
Viarex
Viarox
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anti-Asthmatic Agents
  • Anti-inflammatory Agents
  • Antiarrhythmic Agents
  • Corticosteroids
  • Glucocorticoids
CAS number 5534-09-8
Weight Average: 521.042
Monoisotopic: 520.222781245
Chemical Formula C28H37ClO7
InChI Key InChIKey=KUVIULQEHSCUHY-XYWKZLDCSA-N
InChI
InChI=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
Plain Text
IUPAC Name
2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
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
Plain Text
Mass Spec show (11.1 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older. Also being investigated for oral treatment in mild-to-moderate Crohn's disease of ileal or ileal-right colonic localisation and for "topical" use mild-to-moderate graft versus host disease.
Pharmacodynamics Beclometasone, a synthetic halogenated glucocorticoid with antiinflammatory and vasoconstrictive effects, is used for treating steroid-dependent asthma, allergic or nonallergic rhinitis, or recurrent nasal polyps.
Mechanism of action Unbound corticosteroids cross cell membranes and bind with high affinity to specific cytoplasmic receptors. The result includes inhibition of leukocyte infiltration at the site of inflammation, interference in the function of mediators of inflammatory response, suppression of humoral immune responses, and reduction in edema or scar tissue. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. For the investigated use in the treatment of GvHD or Crohn's, beclometasone acts by binding to interleukin-13 to inhibit cytokines, which in turn inhibits inflammatory chemicals downstream.
Absorption Mean peak plasma concentration was 88pg/ml at 0.5 hour
Volume of distribution Not Available
Protein binding 87% to albumin and transcortin
Metabolism Metabolism mediated via esterase enzymes that are found in most tissues. Undergoes rapid and extensive conversion to beclomenthasone-17-monopropionate (17-BMP) during absorption
Route of elimination Irrespective of the route of administration (injection, oral or inhalation), BDP and its metabolites are mainly excreted in the feces. Less than 10% of the drug and its metabolites are excreted in the urine.
Half life 2.8 hours
Clearance

High plasma clearance after intravenous administration (150 and 120 L/hour).
Toxicity The acute toxicity of beclometasone dipropionate is low. The only harmful effect that follows inhalation of large amounts of the drug over a short period of time is suppression of hypothalamic-pituitary-adrenal (HPA) function. Chronic: The excessive use of beclometasone dipropionate over a long period could lead to adrenal suppression.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Schering corp sub schering plough corp
  • Schering corp
Packagers
Dosage forms
Form Route Strength
Aerosol, metered Nasal
Aerosol, metered Respiratory (inhalation)
Cream Topical
Spray Nasal
Suspension Nasal
Prices
Unit description Cost Unit
Beconase AQ 42 mcg/spray Suspension 25 gm Inhaler 149.32 USD inhaler
Beclomethasone dipro powder 107.1 USD g
Qvar 80 mcg/act Aerosol 7.3 gm Inhaler 105.64 USD inhaler
Qvar 40 mcg/act Aerosol 7.3 gm Inhaler 87.5 USD inhaler
Qvar 80 mcg inhaler 19.05 USD g
Qvar 40 mcg inhaler 15.12 USD g
Propaderm 250 mcg/g Cream 0.46 USD g
Qvar Cfc-Free 100 mcg/dose Metered Dose Aerosol 0.33 USD dose
Qvar Cfc-Free 50 mcg/dose Metered Dose Aerosol 0.16 USD dose
Apo-Beclomethasone 50 mcg/dose Metered Dose Spray 0.06 USD dose
Mylan-Beclo Aq. 50 mcg/dose Metered Dose Spray 0.06 USD dose
Nu-Beclomethasone 50 mcg/dose Metered Dose Spray 0.06 USD dose
First Prev Next Last
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 117-120 °C Not Available
water solubility 49.39 mg/L Not Available
logP 1.3 Not Available
Predicted Properties
Property Value Source
water solubility 2.08e-03 g/l ALOGPS
logP 3.69 ALOGPS
logP 4.43 ChemAxon
logS -5.4 ALOGPS
pKa (strongest acidic) 13.85 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 106.97 ChemAxon
rotatable bond count 8 ChemAxon
refractivity 134.79 ChemAxon
polarizability 54.41 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Willey RF, Milne LJ, Crompton GK, Grant IW: Beclomethasone dipropionate aerosol and oropharyngeal candidiasis. Br J Dis Chest. 1976 Jan;70(1):32-8. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Pubmed
  7. 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. Pubmed
External Links
Resource Link
KEGG Drug D00689 Link_out
KEGG Compound C07813 Link_out
ChEBI 3002 Link_out
ChEMBL 3002 Link_out
Therapeutic Targets Database DAP000416 Link_out
PharmGKB PA448547 Link_out
Drug Product Database 2238796 Link_out
RxList http://www.rxlist.com/qvar-drug.htm Link_out
Drugs.com http://www.drugs.com/cdi/beclomethasone-spray.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Beclometasone_dipropionate Link_out
ATC Codes
  • A07EA07
  • D07AC15
  • R01AD01
  • R03BA01
AHFS Codes
  • 52:08.08
  • 84:06.00
  • 68:04.00
PDB Entries Not Available
FDA label show (255 KB)
MSDS show (73.6 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Saklatvala J: Glucocorticoids: do we know how they work? Arthritis Res. 2002;4(3):146-50. Epub 2002 Jan 21. Pubmed
  2. Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. Pubmed
  3. Usmani OS, Ito K, Maneechotesuwan K, Ito M, Johnson M, Barnes PJ, Adcock IM: Glucocorticoid receptor nuclear translocation in airway cells after inhaled combination therapy. Am J Respir Crit Care Med. 2005 Sep 15;172(6):704-12. Epub 2005 Apr 28. Pubmed
Enzymes

1. Cytochrome P450 3A5

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20815 Link_out
Gene: CYP3A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Carriers

1. Corticosteroid-binding globulin

Actions: binder

Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species

UniProt ID: P08185 Link_out
Gene: SERPINA6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Landyshev IuS, Grigorenko AA, Marikhina NS, Molochnaia SV: [A comparative assessment of the effect of different methods of glucocorticosteroid therapy on the hypophyseal-adrenal system in bronchial asthma patients] Ter Arkh. 1995;67(3):43-7. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19