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Identification
NameBeclomethasone
Accession NumberDB00394  (APRD00564)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Beclomethasone dipropionate is a prodrug of the free form, Beclomethasone (beclomethasone-17-monopropionate). An anti-inflammatory, synthetic corticosteroid, it is used topically as an anti-inflammatory agent and in aerosol form for the treatment of asthma and allergic rhinitis (seasonal and perennial). 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. It is marketed under several brand names such as Qnasl (US) and Rivanase AQ (Canada).

Structure
Thumb
Synonyms
SynonymLanguageCode
(11beta,16beta)-9-chloro-11-Hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dioneNot AvailableNot Available
9-chloro-11beta-Hydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionateNot AvailableNot Available
9-chloro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dioneNot AvailableNot Available
9-chloro-16beta-Methyl-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionateNot AvailableNot Available
9α-chloro-16β-methylprednisoloneNot AvailableNot Available
AerobecNot AvailableNot Available
AldecinNot AvailableNot Available
AnceronNot AvailableNot Available
AndionNot AvailableNot Available
BeclacinNot AvailableNot Available
BecloforteNot AvailableNot Available
BeclometNot AvailableNot Available
BeclometasoneNot AvailableNot Available
Beclometasone 17,21-dipropionateNot AvailableNot Available
Beclometasone dipropionateNot AvailableNot Available
Beclomethasone dipropionateNot AvailableNot Available
BeclorhinolNot AvailableNot Available
BeclovalNot AvailableNot Available
BecloventNot AvailableNot Available
BecodisksNot AvailableNot Available
BeconaseNot AvailableNot Available
BeconasolNot AvailableNot Available
BecotideNot AvailableNot Available
Clenil-aNot AvailableNot Available
EntydermaNot AvailableNot Available
InaloneNot AvailableNot Available
KorbutoneNot AvailableNot Available
PropadermNot AvailableNot Available
Rino-clenilNot AvailableNot Available
SanasthmaxNot AvailableNot Available
SanasthmylNot AvailableNot Available
VancenaseNot AvailableNot Available
VancerilNot AvailableNot Available
ViarexNot AvailableNot Available
ViaroxNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Qvaraerosol, metered40 ugrespiratory (inhalation)STAT Rx USA LLC2000-09-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qvaraerosol, metered40 ugrespiratory (inhalation)Physicians Total Care, Inc.2008-01-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qvaraerosol, metered80 ugrespiratory (inhalation)Physicians Total Care, Inc.2008-01-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qvaraerosol, metered40 ugrespiratory (inhalation)Teva Respiratory, LLC2000-10-062015-11-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qvaraerosol, metered40 ugrespiratory (inhalation)Teva Respiratory, LLC2011-01-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qvaraerosol, metered40 ugrespiratory (inhalation)Teva Respiratory, LLC2014-09-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qvaraerosol, metered80 ugrespiratory (inhalation)Teva Respiratory, LLC2011-01-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qvaraerosol, metered80 ugrespiratory (inhalation)Teva Respiratory, LLC2014-09-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qnaslaerosol, metered40 ugnasalTeva Respiratory, LLC2015-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qnaslaerosol, metered80 ugnasalTeva Respiratory, LLC2012-04-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Propadermcream0.025 %topicalValeant Canada Lp Valeant Canada S.E.C.Not AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Qvarmetered-dose aerosol50 µginhalationValeant Canada Lp Valeant Canada S.E.C.Not AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Qvarmetered-dose aerosol100 µginhalationValeant Canada Lp Valeant Canada S.E.C.Not AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AerobecTeva
AldecinSchering-Plough
AnceronNot Available
AndionNot Available
BeclacinMayado Seiyaku
BecloforteGlaxoSmithKline
BeclometOrion
BeclorhinolChiesi
BeclovalNot Available
BecloventGlaxoSmithKline
BecodisksGlaxoSmithKline
BeconaseGlaxoSmithKline
BeconasolNot Available
BecotideGlaxoSmithKline
Clenil-ANot Available
EntydermaNot Available
InaloneGlaxoSmithKline
KorbutoneNot Available
orBecDOR BioPharma, Inc.
Rino-ClenilChiesi
RivanaseNot Available
SanasthmaxChiesi
SanasthmylNot Available
VancenaseNot Available
VancerilNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number5534-09-8
WeightAverage: 521.042
Monoisotopic: 520.222781245
Chemical FormulaC28H37ClO7
InChI KeyKUVIULQEHSCUHY-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
IUPAC Name
2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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
Taxonomy
DescriptionThis compound 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
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Halohydrin
  • Chlorohydrin
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed in the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older, and in treating symptoms for allergic rhinitis (seasonal or perennial) in patients 12 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.
PharmacodynamicsBeclometasone, 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 actionUnbound 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.
AbsorptionMean peak plasma concentration was 88pg/ml at 0.5 hour
Volume of distribution

The steady state volume of distribution for beclomethasone dipropionate is 20 L, and for it’s active metabolite, beclomethasone-17-monopropionate, it is much larger at 424 L.

Protein binding87% 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 eliminationIrrespective 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 life2.8 hours
Clearance

High plasma clearance after intravenous administration (150 and 120 L/hour).

ToxicityThe 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9904
Blood Brain Barrier+0.9851
Caco-2 permeable+0.5698
P-glycoprotein substrateSubstrate0.7529
P-glycoprotein inhibitor IInhibitor0.5986
P-glycoprotein inhibitor IINon-inhibitor0.7488
Renal organic cation transporterNon-inhibitor0.7907
CYP450 2C9 substrateNon-substrate0.8634
CYP450 2D6 substrateNon-substrate0.9174
CYP450 3A4 substrateSubstrate0.784
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.7516
CYP450 2C19 substrateNon-inhibitor0.9122
CYP450 3A4 substrateNon-inhibitor0.7875
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8577
Ames testNon AMES toxic0.938
CarcinogenicityNon-carcinogens0.914
BiodegradationNot ready biodegradable0.9932
Rat acute toxicity2.1115 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9456
hERG inhibition (predictor II)Non-inhibitor0.6054
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Schering corp sub schering plough corp
  • Schering corp
Packagers
Dosage forms
FormRouteStrength
Aerosol, meterednasal40 ug
Aerosol, meterednasal80 ug
Aerosol, meteredrespiratory (inhalation)40 ug
Aerosol, meteredrespiratory (inhalation)80 ug
Creamtopical0.025 %
Metered-dose aerosolinhalation100 µg
Metered-dose aerosolinhalation50 µg
Prices
Unit descriptionCostUnit
Beconase AQ 42 mcg/spray Suspension 25 gm Inhaler149.32USD inhaler
Beclomethasone dipro powder107.1USD g
Qvar 80 mcg/act Aerosol 7.3 gm Inhaler105.64USD inhaler
Qvar 40 mcg/act Aerosol 7.3 gm Inhaler87.5USD inhaler
Qvar 80 mcg inhaler19.05USD g
Qvar 40 mcg inhaler15.12USD g
Propaderm 250 mcg/g Cream0.46USD g
Qvar Cfc-Free 100 mcg/dose Metered Dose Aerosol0.33USD dose
Qvar Cfc-Free 50 mcg/dose Metered Dose Aerosol0.16USD dose
Apo-Beclomethasone 50 mcg/dose Metered Dose Spray0.06USD dose
Mylan-Beclo Aq. 50 mcg/dose Metered Dose Spray0.06USD dose
Nu-Beclomethasone 50 mcg/dose Metered Dose Spray0.06USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point117-120 °CNot Available
water solubility49.39 mg/LNot Available
logP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00208 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity134.79 m3·mol-1ChemAxon
Polarizability54.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11.1 KB)
SpectraNot Available
References
Synthesis Reference

Taub, D., Wendler, N.L. and Slates, H.L.; US.Patent 3,345,387; October 3, 1967; assigned
to Merck & Co., Inc.

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
  8. FDA label.
External Links
ATC CodesA07EA07D07AC15R01AD01R03BA01
AHFS Codes
  • 52:08.08
  • 68:04.00
  • 84:06.00
PDB EntriesNot Available
FDA labelDownload (255 KB)
MSDSDownload (73.6 KB)
Interactions
Drug Interactions
Drug
AldesleukinMay diminish the antineoplastic effect of Aldesleukin. Exceptions: Beclomethasone (Nasal); Budesonide (Nasal); Ciclesonide (Nasal); Desonide; Dexamethasone (Ophthalmic); Difluprednate; Flunisolide (Nasal); Fluocinolone (Ophthalmic); Fluticasone (Nasal); Loteprednol; Mometasone (Nasal); PrednisoLONE (Ophthalmic); Triamcinolone (Nasal); Triamcinolone (Ophthalmic).
DeferasiroxMay enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased. Exceptions: Beclomethasone (Nasal); Budesonide (Nasal); Ciclesonide (Nasal); Desonide; Dexamethasone (Ophthalmic); Difluprednate; Flunisolide (Nasal); Fluocinolone (Ophthalmic); Fluticasone (Nasal); Loteprednol; Mometasone (Nasal); PrednisoLONE (Ophthalmic); Triamcinolone (Nasal); Triamcinolone (Ophthalmic).
HyaluronidaseMay diminish the therapeutic effect of Hyaluronidase.
TelaprevirMay decrease the serum concentration of Telaprevir. Telaprevir may increase the serum concentration of Corticosteroids.
Food Interactions
  • No food effects were found when given with beclomethasone dipropionate.

Targets

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Corticosteroid-binding globulin P08185 Details

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
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Drug created on June 13, 2005 07:24 / Updated on March 31, 2014 13:28