Identification

Name
Beclomethasone dipropionate
Accession Number
DB00394  (APRD00564, DB11897)
Type
Small Molecule
Groups
Approved, 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
  • (11β,16β)-9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione
  • 9-chloro-11β-hydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate
  • 9-chloro-16β-methyl-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionate
  • beclometasone 17,21-dipropionate
  • Beclometasone dipropionate
External IDs
SCH 18020W / SCH 8020W / SCH-18020W / SGX-201 / SGX-202 / SGX-203
Product Ingredients
IngredientUNIICASInChI Key
Beclomethasone dipropionate monohydrate4H7L9AI22I77011-63-3QHQJZIXSVLFOHD-LYRZEVDOSA-N
Active Moieties
NameKindUNIICASInChI Key
Beclomethasone 17-monopropionateprodrug5BGA9FD55H5534-18-9OHYGPBKGZGRQKT-XGQKBEPLSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Beclodisk - Pwr Inh 100mcg/blisterPowder100 mcgRespiratory (inhalation)Glaxo Wellcome1997-09-032000-05-24Canada
Beclodisk - Pwr Inh 200mcg/blisterPowder200 mcgRespiratory (inhalation)Glaxo Wellcome1997-06-112000-05-24Canada
Beclodisk Pwr 100mcg/blisterPowder100 mcgRespiratory (inhalation)Glaxo Canada Inc1989-12-311998-07-30Canada
Beclodisk Pwr 200mcg/blisterPowder200 mcgRespiratory (inhalation)Glaxo Canada Inc1989-12-311998-07-30Canada
Becloforte 250mcg/aemAerosol, metered250 mcgRespiratory (inhalation)Glaxo Canada Inc1988-12-311998-07-30Canada
Becloforte Inhaler - Aem Inh 250mcg/aemAerosol, metered250 mcgRespiratory (inhalation)Glaxo Wellcome1997-02-112000-05-24Canada
Beclomethasone Aqueous Nasal Spray 50mcg/metered DoseAerosol, metered; Suspension50 mcgNasalPrempharm Inc1997-01-052005-08-05Canada
Beclomethasone Dipropionate Nas-spr 50mcg/aemAerosol, metered50 mcgNasalKenral Inc.1992-12-311997-08-11Canada
Beclomethasone Dipropionate Nasal InhalerAerosol, metered50 mcgNasalPharmaco Canada Inc.1994-12-312001-07-18Canada
Beclomethasone Dipropionate Oral InhalerAerosol, metered50 mcgRespiratory (inhalation)Pharmaco Canada Inc.1994-12-312001-07-18Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-beclomethasone Dipropionate Inhaler 50mcg/mdAerosol, metered50 mcgRespiratory (inhalation)Altimed Pharma Inc.1992-12-312005-05-27Canada
Apo-beclomethasone Nasal SpraySuspension50 mcgNasalApotex Corporation1998-10-07Not applicableCanada
Mylan-beclo AQAerosol, metered; Suspension50 mcgNasalMylan Pharmaceuticals1995-12-31Not applicableCanada
Nu-beclomethasone 50 Mcg/metered Nasal SpraySuspension50 mcgNasalNu Pharm Inc1998-11-242012-09-04Canada
Ratio-beclomethasone AQSpray50 mcgNasalRatiopharm Inc Division Of Teva Canada Limited1995-12-312010-05-21Canada
International/Other Brands
Aerobec (Teva) / Aldecin (Schering-Plough) / Anceron / Andion / Beclacin (Mayado Seiyaku) / Becloforte (GlaxoSmithKline) / Beclomet (Orion) / Beclorhinol (Chiesi) / Becloval / Beclovent (GlaxoSmithKline) / Becodisks (GlaxoSmithKline) / Beconase (GlaxoSmithKline) / Beconasol / Becotide (GlaxoSmithKline) / Clenil-A / Entyderma / Inalone (GlaxoSmithKline) / Korbutone / orBec (DOR BioPharma, Inc.) / Rino-Clenil (Chiesi) / Rivanase / Sanasthmax (Chiesi) / Sanasthmyl / Vancenase / Vanceril
Categories
UNII
5B307S63B2
CAS number
5534-09-8
Weight
Average: 521.042
Monoisotopic: 520.222781245
Chemical Formula
C28H37ClO7
InChI Key
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
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

Pharmacology

Indication

Used 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.

Associated Conditions
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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Human
Absorption

Mean 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 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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Beclomethasone dipropionate.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Beclomethasone dipropionate.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Beclomethasone dipropionate.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Beclomethasone dipropionate.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Beclomethasone dipropionate.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Beclomethasone dipropionate.
4-HydroxytestosteroneThe risk or severity of edema formation can be increased when 4-Hydroxytestosterone is combined with Beclomethasone dipropionate.
5-androstenedioneThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Beclomethasone dipropionate.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when 9-(N-methyl-L-isoleucine)-cyclosporin A is combined with Beclomethasone dipropionate.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Beclomethasone dipropionate.
Food Interactions
  • No food effects were found when given with beclomethasone dipropionate.

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 References
  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:1259918]
  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:3339197]
  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:12839324]
  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:17399941]
  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:17922633]
  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:17244684]
  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:16920559]
External Links
Human Metabolome Database
HMDB0014538
KEGG Drug
D07495
KEGG Compound
C07813
PubChem Compound
21700
PubChem Substance
46509195
ChemSpider
20396
ChEBI
3002
ChEMBL
CHEMBL1200500
Therapeutic Targets Database
DAP000416
PharmGKB
PA448547
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Beclometasone_dipropionate
ATC Codes
R03BA01 — BeclometasoneR03AK08 — Formoterol and beclometasoneA07EA07 — BeclometasoneD07CC04 — Beclometasone and antibioticsR01AD01 — BeclometasoneD07AC15 — Beclometasone
AHFS Codes
  • 68:04.00 — Adrenals
  • 84:06.00 — Anti-inflammatory Agents
  • 52:08.00 — Anti-inflammatory Agents
  • 52:08.08 — Corticosteroids
FDA label
Download (255 KB)
MSDS
Download (73.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableAllergic Rhinitis (AR)1
1CompletedNot AvailableOesophagitis, Eosinophilic1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
1, 2CompletedSupportive CareCancer of the Ovary / Cancer, Breast / Chronic Myeloproliferative Disorders / Gestational Trophoblastic Disease / Graft Versus Host Disease (GVHD) / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Neuroblastomas / Renal Cancers / Testicular germ cell tumour1
2CompletedSupportive CareAccelerated Phase Chronic Myelogenous Leukemia / Adult Acute Lymphoblastic Leukemia in Remission / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Atypical Chronic Myeloid Leukemia / Blastic Phase Chronic Myelogenous Leukemia / Childhood Acute Lymphoblastic Leukemia in Remission / Childhood Acute Myeloid Leukemia in Remission / Childhood Chronic Myelogenous Leukemia / Childhood Myelodysplastic Syndromes / Chronic Eosinophilic Leukemia (CEL) / Chronic Lymphocytic Leukemia (CLL) - Refractory / Chronic Myelomonocytic Leukemia / Chronic Neutrophilic Leukemia / Chronic Phase Chronic Myelogenous Leukemia / Contiguous Stage II Adult Burkitt Lymphoma / Contiguous Stage II Adult Diffuse Large Cell Lymphoma / Contiguous Stage II Adult Diffuse Mixed Cell Lymphoma / Contiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Contiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Contiguous Stage II Adult Lymphoblastic Lymphoma / Contiguous Stage II Grade 1 Follicular Lymphoma / Contiguous Stage II Grade 2 Follicular Lymphoma / Contiguous Stage II Grade 3 Follicular Lymphoma / Contiguous Stage II Mantle Cell Lymphoma / Contiguous Stage II Marginal Zone Lymphoma / Contiguous Stage II Small Lymphocytic Lymphoma / De Novo Myelodysplastic Syndromes / Essential Thrombocythemia (ET) / Extramedullary Plasmacytoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Graft Versus Host Disease (GVHD) / Hematopoietic/Lymphoid Cancer / Isolated Plasmacytoma of Bone / Juvenile Myelomonocytic Leukemia / Meningeal Chronic Myelogenous Leukemia / Myelodysplastic/Myeloproliferative Disease, Unclassifiable / Nodal marginal zone B-cell lymphomas / Noncontiguous Stage II Adult Burkitt Lymphoma / Noncontiguous Stage II Adult Diffuse Large Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Noncontiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Noncontiguous Stage II Adult Lymphoblastic Lymphoma / Noncontiguous Stage II Grade 1 Follicular Lymphoma / Noncontiguous Stage II Grade 2 Follicular Lymphoma / Noncontiguous Stage II Grade 3 Follicular Lymphoma / Noncontiguous Stage II Mantle Cell Lymphoma / Noncontiguous Stage II Marginal Zone Lymphoma / Noncontiguous Stage II Small Lymphocytic Lymphoma / Previously Treated Myelodysplastic Syndromes / Primary Myelofibrosis / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Acute Myeloid Leukemia / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Recurrent/Refractory Childhood Hodgkin Lymphoma / Refractory Hairy Cell Leukemia / Relapsing Chronic Myelogenous Leukemia / Secondary Myelodysplastic Syndromes / Stage I Adult Burkitt Lymphoma / Stage I Adult Diffuse Large Cell Lymphoma / Stage I Adult Diffuse Mixed Cell Lymphoma / Stage I Adult Diffuse Small Cleaved Cell Lymphoma / Stage I Adult Hodgkin Lymphoma / Stage I Adult Immunoblastic Large Cell Lymphoma / Stage I Adult Lymphoblastic Lymphoma / Stage I Adult T-Cell Leukemia/Lymphoma / Stage I Childhood Hodgkin Lymphoma / Stage I Chronic Lymphocytic Leukemia / Stage I Cutaneous T-cell Non-Hodgkin Lymphoma / Stage I Grade 1 Follicular Lymphoma / Stage I Grade 2 Follicular Lymphoma / Stage I Grade 3 Follicular Lymphoma / Stage I Mantle Cell Lymphoma / Stage I Marginal Zone Lymphoma / Stage I Multiple Myeloma / Stage I Mycosis Fungoides/Sezary Syndrome / Stage I Small Lymphocytic Lymphoma / Stage II Adult Hodgkin Lymphoma / Stage II Adult T-Cell Leukemia/Lymphoma / Stage II Chronic Lymphocytic Leukemia / Stage II Cutaneous T-cell Non-Hodgkin Lymphoma / Stage II Multiple Myeloma / Stage II Mycosis Fungoides/Sezary Syndrome / Stage III Adult Burkitt Lymphoma / Stage III Adult Diffuse Large Cell Lymphoma / Stage III Adult Diffuse Mixed Cell Lymphoma / Stage III Adult Diffuse Small Cleaved Cell Lymphoma / Stage III Adult Hodgkin Lymphoma / Stage III Adult Immunoblastic Large Cell Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Adult T-Cell Leukemia/Lymphoma / Stage III Chronic Lymphocytic Leukemia / Stage III Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage III Grade 1 Follicular Lymphoma / Stage III Grade 2 Follicular Lymphoma / Stage III Grade 3 Follicular Lymphoma / Stage III Mantle Cell Lymphoma / Stage III Marginal Zone Lymphoma / Stage III Multiple Myeloma / Stage III Mycosis Fungoides/Sezary Syndrome / Stage III Small Lymphocytic Lymphoma / Stage IV Adult Burkitt Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Adult Diffuse Mixed Cell Lymphoma / Stage IV Adult Diffuse Small Cleaved Cell Lymphoma / Stage IV Adult Hodgkin Lymphoma / Stage IV Adult Immunoblastic Large Cell Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Adult T-Cell Leukemia/Lymphoma / Stage IV Chronic Lymphocytic Leukemia / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IV Grade 1 Follicular Lymphoma / Stage IV Grade 2 Follicular Lymphoma / Stage IV Grade 3 Follicular Lymphoma / Stage IV Marginal Zone Lymphoma / Stage IV Mycosis Fungoides/Sezary Syndrome / Stage IV Small Lymphocytic Lymphoma1
2CompletedTreatmentAsthma Bronchial1
2CompletedTreatmentAsthma Bronchial / Bronchial Hyperresponsiveness1
2CompletedTreatmentHayfever / Seasonal Allergic Rhinitis (SAR)1
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentRhinitis, Allergic, Seasonal1
2RecruitingOtherAsthma Bronchial1
2RecruitingTreatmentAsthma Bronchial1
2RecruitingTreatmentChronic Lung Disease of Prematurity1
2TerminatedTreatmentChronic Gastrointestinal Graft vs Host Disease1
2Unknown StatusTreatmentPolyps, Nasal1
2WithdrawnTreatmentAsthma Bronchial1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sinusitis1
2, 3CompletedTreatmentAsthma Bronchial1
2, 3SuspendedTreatmentFolliculitis1
3CompletedNot AvailableChronic Lung Disease of Prematurity / Chronic Lung Diseases / Hyaline Membrane Disease1
3CompletedSupportive CareGraft Versus Host Disease (GVHD)1
3CompletedTreatmentAcute Rhinosinusitis1
3CompletedTreatmentAllergic Rhinitis (AR)2
3CompletedTreatmentAllergic Rhinitis (AR) / Asthma Bronchial1
3CompletedTreatmentAsthma Bronchial13
3CompletedTreatmentAsthma Bronchial / Chronic Lung Diseases1
3CompletedTreatmentBronchial Asthma1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentGastrointestinal Graft-Versus-Host Disease / Graft Versus Host Disease (GVHD)1
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)1
3CompletedTreatmentPollen Allergy / Seasonal Allergic Rhinitis (SAR)1
3CompletedTreatmentRespiratory Tract Diseases / Wheezing1
3CompletedTreatmentRhinitis, Allergic, Perennial3
3CompletedTreatmentSeasonal Allergic Rhinitis (SAR) / Severe Acute Respiratory Syndrome1
3Not Yet RecruitingTreatmentAsthma Bronchial1
3TerminatedTreatmentAcute Gastrointestinal Graft vs Host Disease1
4CompletedPreventionBronchial Spasm / Respiratory Sounds / Respiratory Tract Infections (RTI)1
4CompletedPreventionSeasonal Allergic Rhinitis (SAR)1
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentAllergic Rhinitis (AR) / Asthma Bronchial1
4CompletedTreatmentAsthma Bronchial6
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
4Enrolling by InvitationTreatmentAsthma Bronchial1
4Not Yet RecruitingPreventionAnesthesia, Endotracheal1
4RecruitingTreatmentAsthma Bronchial / Pediatric ALL1
4RecruitingTreatmentPulmonary Disease,Chronic Obstructive1
4TerminatedOtherChronic Obstructive Pulmonary Disease (COPD)1
4TerminatedTreatmentAsthma Bronchial1
4TerminatedTreatmentDyspnea / Wheezing1
4Unknown StatusDiagnosticChronic Obstructive Pulmonary Disease (COPD) / Emphysema / Small Airway Disease1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4WithdrawnTreatmentWheezing1
Not AvailableActive Not RecruitingBasic ScienceAsthma Bronchial1
Not AvailableActive Not RecruitingTreatmentAsthma Bronchial1
Not AvailableCompletedNot AvailableAllergic Rhinitis (AR)1
Not AvailableCompletedNot AvailableAsthma Bronchial5
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedNot AvailablePerennial Allergic Rhinitis (PAR)1
Not AvailableCompletedSupportive CareGraft Versus Host Disease (GVHD)1
Not AvailableCompletedTreatmentIntraocular Pressure1
Not AvailableRecruitingNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingHealth Services ResearchAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
Not AvailableTerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableUnknown StatusNot AvailableAllergic Rhinitis (AR) / Asthma Bronchial1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
  • Schering corp sub schering plough corp
  • Schering corp
Packagers
  • 3M Health Care
  • A-S Medication Solutions LLC
  • Dispensing Solutions
  • GlaxoSmithKline Inc.
  • Graceway Pharmaceuticals
  • Medisca Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
PowderRespiratory (inhalation)100 mcg
PowderRespiratory (inhalation)200 mcg
Aerosol, meteredRespiratory (inhalation)250 mcg
CapsuleRespiratory (inhalation)100 mcg
CapsuleRespiratory (inhalation)200 mcg
Spray, suspensionNasal42 ug/1
Aerosol, meteredNasal50 mcg
Aerosol, metered; suspensionNasal50 mcg
SuspensionNasal50 mcg
CreamTopical0.025 %
CreamTopical.025 %
LotionTopical.025 %
LotionTopical0.025 %
Aerosol, meteredNasal40 mcg
Aerosol, meteredNasal40 ug/1
Aerosol, meteredNasal80 mcg
Aerosol, meteredNasal80 ug/1
Aerosol, meteredRespiratory (inhalation)100 mcg
Aerosol, meteredRespiratory (inhalation)40 ug/1
Aerosol, meteredRespiratory (inhalation)50 mcg
Aerosol, meteredRespiratory (inhalation)80 ug/1
SprayNasal50 mcg
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5776432No1995-07-072015-07-07Us
US6446627No1997-12-182017-12-18Us
US8132712No2008-09-072028-09-07Us
US7780038No2007-01-242027-01-24Us
US9463289No2011-05-182031-05-18Us
US8931476No2011-07-172031-07-17Us
US7637260No2000-08-252020-08-25Us
US9808587No2011-05-182031-05-18Us
US10022510No2011-05-182031-05-18Us
US10022509No2011-05-182031-05-18Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)117-120 °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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.7516
CYP450 2C19 inhibitorNon-inhibitor0.9122
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.1 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0536-0000390000-d1146b326a2bf27937e3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0489240000-9581961e5dddfb7a403f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0h71-3892000000-454fb634c4339a1ebfe0

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Steroid esters / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Alpha-acyloxy ketones / Dicarboxylic acids and derivatives / Secondary alcohols / Carboxylic acid esters
show 7 more
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
show 23 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
propanoate ester, enone, 11beta-hydroxy steroid, glucocorticoid, steroid ester, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, chlorinated steroid, corticosteroid (CHEBI:3002)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Saklatvala J: Glucocorticoids: do we know how they work? Arthritis Res. 2002;4(3):146-50. Epub 2002 Jan 21. [PubMed:12010562]
  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:16507850]
  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:15860753]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Hukkanen J, Vaisanen T, Lassila A, Piipari R, Anttila S, Pelkonen O, Raunio H, Hakkola J: Regulation of CYP3A5 by glucocorticoids and cigarette smoke in human lung-derived cells. J Pharmacol Exp Ther. 2003 Feb;304(2):745-52. [PubMed:12538830]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Roberts JK, Moore CD, Ward RM, Yost GS, Reilly CA: Metabolism of beclomethasone dipropionate by cytochrome P450 3A enzymes. J Pharmacol Exp Ther. 2013 May;345(2):308-16. doi: 10.1124/jpet.112.202556. Epub 2013 Mar 19. [PubMed:23512537]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
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:7770804]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on September 23, 2018 19:37