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Identification
- Summary
Beclomethasone dipropionate is an inhaled corticosteroid used as maintenance treatment in the prophylaxis of asthma attacks.
- Brand Names
- Alanase, Beconase, Propaderm, Qnasl, Qvar, Rivanase AQ
- Generic Name
- Beclomethasone dipropionate
- DrugBank Accession Number
- DB00394
- Background
Beclomethasone dipropionate is a second-generation10 synthetic corticosteroid and diester of beclomethasone, which is structurally similar to dexamethasone.11 It is a prodrug of an active metabolite beclomethasone 17-monopropionate (17-BMP)1 which acts on the glucocorticoid receptor to mediates its therapeutic action. Beclomethasone dipropionate itself posesses weak glucocorticoid receptor binding affinity and is rapidly converted into 17-BMP upon administration.1 Formulations for oral inhalation, intranasal, and topical use are available for beclomethasone dipropionate. Beclomethasone dipropionate became first available in a pressurized metered-dose inhaler in 1972 and later in a dry powder inhaler and an aqueous nasal spray.1 Due to its anti-inflammatory, antipruritic, and anti-allergy properties, beclomethasone dipropionate is used in various inflammatory conditions, such as asthma, allergic rhinitis, and dermatoses to reduce symptoms. When inhaled, it is proposed that beclomethasone dipropionate remains active locally in the lung without causing significant side effects associated with systemic corticosteroids.8 Compared to earlier corticosteroids such as dexamethasone and prednisolone, beclomethasone dipropionate is reported to be less irritating to the nasal mucosa with a longer duration of action when administered intranasally.3
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Beclomethasone dipropionate (DB00394)
- Weight
- Average: 521.042
Monoisotopic: 520.222781245 - Chemical Formula
- C28H37ClO7
- 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
- Beclometasone dipropionate anhydrous
- Beclometasone dipropionato
- Beclomethasone dipropionate
- External IDs
- SCH 18020W
- SCH 8020W
- SCH-18020W
- SGX-201
- SGX-202
- SGX-203
Pharmacology
- Indication
Indicated for oral inhalation use in the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older. The aerosol form of beclomethasone diproprionate is not indicated for the relief of acute bronchospasm.11
Indicated for intranasal use to relieve the symptoms of seasonal or perennial allergic and nonallergic (vasomotor) rhinitis and prevent the recurrence of nasal polyps following surgical removal.12
Indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients 13 years of age and older.14 Corticosteroid-responsive dermatoses include psoriasis, contact dermatitis (dermatitis venenata), atopic dermatitis (infantile eczema, allergic dermatitis), neurodermatitis (lichen simplex chronicus, lichen planus, eczema, eczematous dermatitis), intertrigo, dyshidroses (pompholyx), seborrheic dermatitis, exfoliative dermatitis, solar dermatitis, stasis dermatitis, and anogenital and senile pruritus.13
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in treatment of Acute bacterial rhinosinusitis ••• ••••• ••••• Used as adjunct in combination to manage Asthma Combination Product in combination with: Albuterol (DB01001) •••••••••••• ••••••• Management of Asthma •••••••••••• •••••••• Symptomatic treatment of Chronic rhinosinusitis ••• ••••• ••••• Symptomatic treatment of Dermatosis •••••••••••• ••••••••••• ••••• ••••••••••••••••••••••••• ••••••• •••••••• - Contraindications & Blackbox Warnings
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Inflammatory conditions, including asthma, dermatoses, and allergic rhinitis, involve the activation of cascades by inflammatory mediators. Inflammation is a primary defense mechanism and the homeostatic response of the immune system; however, a prolonged inflammatory response in certain disorders may lead to tissue damage, pain, and swelling. Beclomethasone dipropionate works by attenuating the inflammatory responses associated with asthma, allergic rhinitis, nasal polyps, and corticosteroid-responsive dermatoses. It suppresses the actions of inflammatory cells, such as mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils. It also inhibits the release of inflammatory mediators, such as histamine, eicosanoids, leukotrienes, and cytokines.11 Beclomethasone dipropionate is reported to exhibit potent topical activity while possessing low systemic effects.2
Beclomethasone dipropionate is a corticosteroid drug with anti-inflammatory and vasoconstrictive effects used to treat chronic inflammatory processes such as asthma, allergic rhinitis, corticosteroid-responsive dermatoses. When inhaled, it improves lung function, decreases airway hyper-reactivity, and reduces the severity of asthmatic symptoms.9 Although inhaled corticosteroids, including beclomethasone dipropionate, are reported to mainly act locally in the lungs, systemic effects such as disruption of hypothalamic-pituitary-adrenal (HPA) axis function, bone turnover, osteoporosis, and growth suppression may still be observed with chronic use or high dose administration. There were varying findings from clinical studies examining the effect of beclomethasone dipropionate on growth suppression in pediatric patients.9 It was shown to suppress the hypothalamo-pituitary-adrenal (HPA) axis in a dose-dependent manner.6 HPA axis is a central hormonal response system to stress and activation of HPA axis leads to the production of endogenous steroid hormone production.7 Long-term use of high-dose systemic corticosteroids, including those inhaled, was often associated with signs and symptoms of adrenal insufficiency when exposed to stress conditions, such as trauma, surgery, or infections. As corticosteroids work by suppressing the immune system, there may be an increased risk for developing infections.11 Cases of Candida albicans infection of the mouth and throat have been reported with inhaled beclomethasone dipropionate therapy.8
- Mechanism of action
Beclomethasone dipropionate is a corticosteroid and prodrug that is rapidly activated by hydrolysis to the active monoester, 17 monopropionate (17-BMP), which mediates anti-inflammatory actions. 17-BMP has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor which is approximately 13 times that of dexamethasone and 25 times that of beclomethasone dipropionate.11 Upon binding of the ligand, the glucocorticoid receptors dimerize and translocate into the nucleus, where they subsequently bind to glucocorticoid response elements (GRE) on glucocorticoid-responsive genes, leading to changes in transcription. There are several proposed mechanisms for the anti-inflammatory action of corticosteroids. Corticosteroids may work by increasing the transcription of genes coding for anti-inflammatory proteins, including lipocortin-1 and interleukin-10.4 Corticosteroids were also shown to inhibit the expression of multiple genes that encode pro-inflammatory factors, such as cytokines, chemokines, and adhesion molecules, that are activated during the chronic inflammatory process.5 This is thought to be due to the direct inhibitory interaction between activated glucocorticoid receptors and activated pro-inflammatory transcription factors, such as nuclear factor-kappa B and activator protein-1.4 Chronic inflammation is often characterized by enhanced expression of these transcription factors that bind to and activate coactivator molecules, which then acetylate core histones to switch on gene transcription to further amplify the inflammatory process.5 Corticosteroids suppress the multiple inflammatory gene expression by promoting histone deacetylation, resulting in tighter coiling of DNA and reduced access of transcription factors to their binding sites.4
Target Actions Organism AGlucocorticoid receptor agonistHumans - Absorption
Following oral inhalation of 320 mcg of beclomethasone dipropionate (BDP), the Cmax was 88 pg/mL and it was reached after 0.5 at post-administration. The mean Cmax of the major and most active metabolite, beclomethasone-17-monopropionate (17-BMP), was 1419 pg/mL at 0.7 hour post-dosing.11
In another pharmacokinetic study, the AUC of BDP and 17-BMP were 6660 and 6185 pgxh/mL, respectively. The Cmax was 35356 pg/mL for BDP and 2633 pg/mL for 17-BMP, and and the median time to reach these concentrations (Tmax) was 0.2 hours. In the same study, the AUC of 17-BMP following oral and intranasal administration were 10158 and 3660 pgxh/mL, respectively. The Cmax of 17-BMP following oral and intranasal administration were 703 and 310 pg/mL, respectively, and the Tmax was 4 hours. The total bioavailability of 17-BMP following oral and intranasal administration were 41% and 44%, respectively.1
- Volume of distribution
Following intravenous administration, the steady-state volume of distribution was 20 L for beclomethasone dipropionate and 424 L for the active metabolite, beclomethasone-17-monopropionate.1
- Protein binding
Based on the findings of in vitro studies, the protein binding of the main active metabolite, beclomethasone-17-monopropionate (17-BMP), was 94-96% over the concentration range of 1000 to 5000 pg/mL.11
- Metabolism
During absorption, beclomethasone dipropionate is undergoes rapid and extensive hydrolysis mediated by esterases CYP3A to form beclomethasone-17-monopropionate (17-BMP), beclomethasone-21-monopropionate (21-BMP), and beclomethasone (BOH). 17-BMP is the major active metabolite with the most potent anti-inflammatory activity.11 About 95% of the total beclomethasone dipropionate administered via oral inhalation undergoes presystemic conversion to form 17-BMP in the lung.1
Hover over products below to view reaction partners
- Route of elimination
Regardless of the route of administration, beclomethasone dipropionate and its metabolites are predominantly excreted in the feces, with less than 10% of the drug and its metabolites being excreted in the urine.11 12
- Half-life
Following intravenous administration, the half life of beclomethasone dipropionate was 0.5 hours while the half life of the active metabolite 17-BMP was 2.7 hours. Following oral and intranasal administration, the half life of 17-BMP was 8.8 and 5.7 hours, respectively.1
- Clearance
Following intravenous administration, the clearance of beclomethasone dipropionate and 17-BMP were 150 L/h and 120 L/h, respectively.1
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral LD50 in rats is >3750 mg/kg.MSDS
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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Beclomethasone dipropionate can be increased when it is combined with Abametapir. Abatacept The risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Beclomethasone dipropionate. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Beclomethasone dipropionate. Acarbose The risk or severity of hyperglycemia can be increased when Beclomethasone dipropionate is combined with Acarbose. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Beclomethasone dipropionate monohydrate 4H7L9AI22I 77011-63-3 QHQJZIXSVLFOHD-LYRZEVDOSA-N - Active Moieties
Name Kind UNII CAS InChI Key Beclomethasone 17-monopropionate prodrug 5BGA9FD55H 5534-18-9 OHYGPBKGZGRQKT-XGQKBEPLSA-N - 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
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Beclodisk - Pwr Inh 100mcg/blister Powder 100 mcg / blister Respiratory (inhalation) Glaxo Wellcome Indonesia 1997-09-03 2000-05-24 Canada 
Beclodisk - Pwr Inh 200mcg/blister Powder 200 mcg / blister Respiratory (inhalation) Glaxo Wellcome Indonesia 1997-06-11 2000-05-24 Canada Beclodisk Pwr 100mcg/blister Powder 100 mcg / blister Respiratory (inhalation) Glaxo Canada Inc 1989-12-31 1998-07-30 Canada Beclodisk Pwr 200mcg/blister Powder 200 mcg / blister Respiratory (inhalation) Glaxo Canada Inc 1989-12-31 1998-07-30 Canada Becloforte 250mcg/aem Aerosol, metered 250 mcg / act Respiratory (inhalation) Glaxo Canada Inc 1988-12-31 1998-07-30 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alti-beclomethasone Dipropionate Inhaler 50mcg/md Aerosol, metered 50 mcg / act Respiratory (inhalation) Altimed Pharma Inc. 1992-12-31 2005-05-27 Canada Apo-beclomethasone Nasal Spray Suspension 50 mcg / act Nasal Apotex Corporation 1998-10-07 Not applicable Canada Mylan-beclo AQ Aerosol, metered; Suspension 50 mcg / act Nasal Mylan Pharmaceuticals Inc. 1995-12-31 Not applicable Canada Ratio-beclomethasone AQ Spray 50 mcg / act Nasal Ratiopharm Inc Division Of Teva Canada Limited 1995-12-31 2010-05-21 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ALABASTER Beclomethasone dipropionate (100 MICROGRAMMI) + Formoterol fumarate (6 mcg) Powder Respiratory (inhalation) Master Pharma S.R.L. 2014-07-08 Not applicable Italy 
ALABASTER Beclomethasone dipropionate (100 MICROGRAMMI) + Formoterol fumarate (6 mcg) Powder Respiratory (inhalation) Master Pharma S.R.L. 2020-03-14 Not applicable Italy ALABASTER Beclomethasone dipropionate (100 mcg) + Formoterol fumarate (6 mcg) Aerosol, powder Respiratory (inhalation) Master Pharma S.R.L. 2014-07-08 Not applicable Italy ALABASTER Beclomethasone dipropionate (200 mcg) + Formoterol fumarate (12 mcg) Powder, metered Respiratory (inhalation) Master Pharma S.R.L. 2020-09-09 Not applicable Italy ALABASTER Beclomethasone dipropionate (200 mcg) + Formoterol fumarate (6 mcg) Aerosol, powder Respiratory (inhalation) Master Pharma S.R.L. 2017-01-02 Not applicable Italy
Categories
- ATC Codes
- D07CC04 — Beclometasone and antibiotics
- D07CC — Corticosteroids, potent, combinations with antibiotics
- D07C — CORTICOSTEROIDS, COMBINATIONS WITH ANTIBIOTICS
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03BA — Glucocorticoids
- R03B — OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- D07AC — Corticosteroids, potent (group III)
- D07A — CORTICOSTEROIDS, PLAIN
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R01AD — Corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenal Cortex Hormones
- Adrenals
- Agents to Treat Airway Disease
- Alimentary Tract and Metabolism
- Anti-Asthmatic Agents
- Anti-Inflammatory Agents
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- BCRP/ABCG2 Inhibitors
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids Acting Locally
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs for Obstructive Airway Diseases
- Fused-Ring Compounds
- Glucocorticoids
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Immunosuppressive Agents
- Intestinal Antiinflammatory Agents
- Nasal Preparations
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- P-glycoprotein inducers
- P-glycoprotein substrates
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Respiratory System Agents
- Steroids
- Steroids, Chlorinated
- Thyroxine-binding globulin inhibitors
- Chemical TaxonomyProvided by Classyfire
- 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
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl chloride / Alkyl halide 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)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5B307S63B2
- CAS number
- 5534-09-8
- 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,3aS,3bS,9aS,9bR,10S,11aS)-9b-chloro-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1-(propanoyloxy)-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-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
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
- Daley-Yates PT, Price AC, Sisson JR, Pereira A, Dallow N: Beclomethasone dipropionate: absolute bioavailability, pharmacokinetics and metabolism following intravenous, oral, intranasal and inhaled administration in man. Br J Clin Pharmacol. 2001 May;51(5):400-9. doi: 10.1046/j.0306-5251.2001.01374.x. [Article]
- Brogden RN, Heel RC, Speight TM, Avery GS: Beclomethasone dipropionate. A reappraisal of its pharmacodynamic properties and therapeutic efficacy after a decade of use in asthma and rhinitis. Drugs. 1984 Aug;28(2):99-126. doi: 10.2165/00003495-198428020-00002. [Article]
- Edwards TB: Effectiveness and safety of beclomethasone dipropionate, an intranasal corticosteroid, in the treatment of patients with allergic rhinitis. Clin Ther. 1995 Nov-Dec;17(6):1032-41. [Article]
- Barnes PJ: Anti-inflammatory actions of glucocorticoids: molecular mechanisms. Clin Sci (Lond). 1998 Jun;94(6):557-72. [Article]
- Barnes PJ: How corticosteroids control inflammation: Quintiles Prize Lecture 2005. Br J Pharmacol. 2006 Jun;148(3):245-54. doi: 10.1038/sj.bjp.0706736. [Article]
- Grebe SK, Feek CM, Durham JA, Kljakovic M, Cooke RR: Inhaled beclomethasone dipropionate suppresses the hypothalamo-pituitary-adrenal axis in a dose dependent manner. Clin Endocrinol (Oxf). 1997 Sep;47(3):297-304. [Article]
- Dluhy RG: Clinical relevance of inhaled corticosteroids and HPA axis suppression. J Allergy Clin Immunol. 1998 Apr;101(4 Pt 2):S447-50. [Article]
- Wilcox JB, Avery GS: Beclomethasone dipropionate corticosteroid inhaler: a preliminary report of its pharmacological properties and therapeutic efficacy in asthma. Drugs. 1973;6(2):84-93. doi: 10.2165/00003495-197306020-00002. [Article]
- Philip J: The effects of inhaled corticosteroids on growth in children. Open Respir Med J. 2014 Dec 31;8:66-73. doi: 10.2174/1874306401408010066. eCollection 2014. [Article]
- Rizzello F, Mazza M, Salice M, Calabrese C, Calafiore A, Campieri M, Gionchetti P: The safety of beclomethasone dipropionate in the treatment of ulcerative colitis. Expert Opin Drug Saf. 2018 Sep;17(9):963-969. doi: 10.1080/14740338.2018.1510914. Epub 2018 Aug 21. [Article]
- QVAR® (beclomethasone dipropionate HFA) for oral inhalation use - FDA Label [Link]
- BECONASE AQ® (beclomethasone dipropionate, monohydrate) for intranasal use only - FDA Label [Link]
- DIPROSONE® (Betamethasone Dipropionate Cream) - Product Monograph - Merck Canada Inc. [Link]
- DIPROLENE® (augmented betamethasone dipropionate) ointment, for topical use - FDA Label [Link]
- External Links
- Human Metabolome Database
- HMDB0014538
- KEGG Drug
- D07495
- KEGG Compound
- C07813
- PubChem Compound
- 21700
- PubChem Substance
- 46509195
- ChemSpider
- 20396
- 1348
- ChEBI
- 3002
- ChEMBL
- CHEMBL1200500
- ZINC
- ZINC000003938744
- Therapeutic Targets Database
- DAP000416
- PharmGKB
- PA448547
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Beclometasone
- MSDS
- Download (55.8 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Allergic Rhinitis (AR) 1 somestatus stop reason just information to hide Not Available Completed Not Available Asthma 8 somestatus stop reason just information to hide Not Available Completed Not Available Asthma / Obesity 1 somestatus stop reason just information to hide Not Available Completed Not Available Chronic Obstructive Pulmonary Disease (COPD) 4 somestatus stop reason just information to hide Not Available Completed Not Available Perennial Allergic Rhinitis (PAR) 1 somestatus stop reason just information to hide
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
Form Route Strength Spray, metered Nasal 50 mcg Powder, metered Respiratory (inhalation) Aerosol Buccal 0.989 mg Aerosol Respiratory (inhalation) 100 mcg Aerosol, metered Nasal 50 mcg Aerosol, spray Respiratory (inhalation) Aerosol Respiratory (inhalation) 0.08287 g Powder Respiratory (inhalation) 100 mcg / blister Powder Respiratory (inhalation) 200 mcg / blister Solution Buccal; Respiratory (inhalation) 0.25 mg Aerosol, metered Respiratory (inhalation) 250 mcg / act Gas Respiratory (inhalation) 100 UG Aerosol Respiratory (inhalation) 0.329 g Aerosol Respiratory (inhalation) 0.066 g Spray Nasal 100 UG Aerosol, powder Respiratory (inhalation) 0.1 MG Aerosol, powder Respiratory (inhalation) 0.4 MG Aerosol, powder Respiratory (inhalation) 0.1 mg/1 Aerosol, powder Respiratory (inhalation) 0.2 mg/1 Aerosol, powder Respiratory (inhalation) 0.4 mg/1 Aerosol, powder Respiratory (inhalation) 0.2 MG Powder, metered Respiratory (inhalation) 180 mcg Powder Respiratory (inhalation) 200 mcg/1dose Powder Respiratory (inhalation) Powder, metered Respiratory (inhalation) 200 MCG Spray, suspension Nasal 50 mcg/1dose Spray Nasal 0.05 MG Spray Nasal 0.10 MG Gas Respiratory (inhalation) 200 UG Gas Respiratory (inhalation) 0.05 MG Gas Respiratory (inhalation) 0.10 MG Gas Respiratory (inhalation) 0.20 MG Gas Respiratory (inhalation) 0.25 MG Spray Nasal 50 UG Suspension Respiratory (inhalation) 0.025 mg Suspension Respiratory (inhalation) 10 mg Suspension Respiratory (inhalation) 0.011 g Suspension Respiratory (inhalation) 0.01 g Suspension Respiratory (inhalation) 0.062 % w/v Suspension Respiratory (inhalation) 0.329 g Aerosol Respiratory (inhalation) 50 mcg Aerosol Intrasinal 0.07 % Aerosol Respiratory (inhalation) 0.07 % Solution Respiratory (inhalation) 0.09549 % w/w Aerosol Respiratory (inhalation) 10 mg Aerosol Respiratory (inhalation) 89.29 g Aerosol, metered Respiratory (inhalation) 100 MICROGRAMMI Aerosol, metered Respiratory (inhalation) 200 MICROGRAMMI Aerosol, metered Respiratory (inhalation) 250 MICROGRAMMI Aerosol, metered Respiratory (inhalation) 50 MICROGRAMMI Suspension Respiratory (inhalation) 400 MICROGRAMMI Suspension Respiratory (inhalation) 800 MICROGRAMMI Aerosol, metered Nasal; Respiratory (inhalation) 50 mcg / act Suspension Nasal 50 mcg / act Aerosol Respiratory (inhalation) 0.328 % w/w Aerosol Respiratory (inhalation) 0.06579 g Aerosol Respiratory (inhalation) 0.0658 % w/w Aerosol Respiratory (inhalation) 0.08 % w/w Suspension Respiratory (inhalation) Suspension Intrasinal; Nasal 0.05 g Spray Nasal 0.05 mg/0.13mL Suspension Nasal; Respiratory (inhalation) 51.73 mcg Suspension Respiratory (inhalation) 0.32895 % w/w Aerosol Respiratory (inhalation) 0.06579 % w/v Solution Respiratory (inhalation) 0.06579 % w/v Capsule Respiratory (inhalation) 100 mcg / cap Capsule Respiratory (inhalation) 200 mcg / cap Suspension Rectal Tablet, delayed release Oral Spray Nasal 50 mcg/1dose Spray, suspension Nasal 42 ug/1 Spray, metered Nasal Aerosol, metered Nasal 50 mcg / act Aerosol, metered Respiratory (inhalation) 10 MG Spray Nasal 10 ML Spray, suspension Respiratory (inhalation) 200 MICROGRAMMI/ML Aerosol Respiratory (inhalation) Spray, suspension Nasal 100 mcg Cream Topical 0.025 % Ointment Topical 0.025 % Cream Topical 15 g Cream Topical 5 g Suspension Respiratory (inhalation) 0.0832 g Aerosol, metered Respiratory (inhalation) 200 MCG Powder, metered Respiratory (inhalation) 100 MCG Powder, metered Respiratory (inhalation) 400 MCG Aerosol, metered Respiratory (inhalation) 100 mcg Aerosol Respiratory (inhalation) 0.5 g Aerosol Respiratory (inhalation) 0.1 % Lotion Topical Cream Cutaneous Cream Topical 0.025 % w/w Aerosol Buccal 0.8475 mg Aerosol Respiratory (inhalation) 50 cg Suspension Respiratory (inhalation) 50 mg Powder Respiratory (inhalation) 100 MICROGRAMMI Powder Respiratory (inhalation) 200 MICROGRAMMI Powder Respiratory (inhalation) 400 MICROGRAMMI Spray Nasal 30 ML Suspension Respiratory (inhalation) 400 mcg/ml Spray Nasal 250 mcg/1dose Aerosol Respiratory (inhalation) 250 mcg Aerosol, metered Respiratory (inhalation) 50 mcg Aerosol; suspension Respiratory (inhalation) Spray, suspension Respiratory (inhalation) Aerosol Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) 250 mcg Solution Respiratory (inhalation) 250 cg Solution Respiratory (inhalation) 50 cg Aerosol; suspension Respiratory (inhalation) 50 MCG Suspension Respiratory (inhalation) 0.800 mg Suspension Rectal 3 MG/60ML Tablet, delayed release Oral 5 MG Aerosol Buccal 0.859 mg Cream Topical Capsule Respiratory (inhalation) 0.1 mg/1 Capsule Respiratory (inhalation) 0.2 mg/1 Capsule Respiratory (inhalation) 0.4 mg/1 Spray Nasal 50 mcg Ointment Topical Aerosol Respiratory (inhalation) 0.07 % w/w Solution Respiratory (inhalation) 0.42 % w/w Aerosol, spray Respiratory (inhalation) Capsule Respiratory (inhalation) Solution Respiratory (inhalation) Gas Respiratory (inhalation) Aerosol, powder Respiratory (inhalation) Powder, metered Respiratory (inhalation) Powder Respiratory (inhalation) Powder, metered Respiratory (inhalation) 100 mcg Aerosol, metered Respiratory (inhalation) 0.100 mg Cream Topical Aerosol Buccal 0.833 mg Aerosol, metered Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) Spray Nasal Aerosol Buccal Aerosol, metered; solution Respiratory (inhalation) Powder Buccal Gas Respiratory (inhalation) 50 UG Aerosol, foam Rectal 3 MG Lotion Cutaneous Lotion Topical 0025 % Ointment Cutaneous Ointment Topical 0.25 mg/g Ointment Topical 30 G Solution Topical Cream Topical 0.25 MG/G Ointment Topical 0025 % Solution Cutaneous; Topical 0.25 MG/G Cream Topical 0025 % Aerosol Buccal 0.4347 g Aerosol, metered; suspension Nasal 50 mcg / act Solution Respiratory (inhalation) 250 mcg Solution Respiratory (inhalation) 50 mcg Spray, suspension Respiratory (inhalation) 0.04 % Cream Topical 0.025 % w/w Cream Topical .025 % Lotion Topical .025 % Lotion Topical 0.025 % Aerosol, metered Nasal 40 ug/1 Aerosol, metered Nasal 40 mcg / act Aerosol, metered Nasal 80 ug/1 Aerosol, metered Nasal 80 mcg / act Aerosol, metered Respiratory (inhalation) 100 mcg / act Aerosol, metered Respiratory (inhalation) 40 ug/1 Aerosol, metered Respiratory (inhalation) 50 mcg / act Aerosol, metered Respiratory (inhalation) 80 ug/1 Spray Nasal 50 mcg / act Spray Nasal 0.1 MG Solution Nasal 77.00 mg Spray Nasal 100 MCG Aerosol Respiratory (inhalation) 0.1 g Suspension Intrasinal; Nasal 0.0505 g Gas Respiratory (inhalation) 250 UG Gas Respiratory (inhalation) 50 µg Cream Topical 0.5 mg/g Aerosol, foam Rectal 42 MG Suppository 3 MG Suspension Rectal 3 MG Aerosol Respiratory (inhalation) 0.1497 g Aerosol Respiratory (inhalation) 0.3743 g Aerosol Buccal 0.0588 g Aerosol Respiratory (inhalation) 250 mcg/1dose Aerosol, metered Respiratory (inhalation) 50 mcg/1dose Spray, suspension Nasal 100 mcg/1dose Aerosol Respiratory (inhalation) 100 mcg/1dose Aerosol Respiratory (inhalation) 200 mcg/1dose Aerosol Respiratory (inhalation) 50 mcg/1dose - Prices
Unit description Cost Unit Beconase AQ 42 mcg/spray Suspension 25 gm Inhaler 149.32USD inhaler Beclomethasone dipro powder 107.1USD g Qvar 80 mcg/act Aerosol 7.3 gm Inhaler 105.64USD inhaler Qvar 40 mcg/act Aerosol 7.3 gm Inhaler 87.5USD inhaler Qvar 80 mcg inhaler 19.05USD g Qvar 40 mcg inhaler 15.12USD g Propaderm 250 mcg/g Cream 0.46USD g Qvar Cfc-Free 100 mcg/dose Metered Dose Aerosol 0.33USD dose Qvar Cfc-Free 50 mcg/dose Metered Dose Aerosol 0.16USD dose Apo-Beclomethasone 50 mcg/dose Metered Dose Spray 0.06USD dose Mylan-Beclo Aq. 50 mcg/dose Metered Dose Spray 0.06USD dose Nu-Beclomethasone 50 mcg/dose Metered Dose Spray 0.06USD dose DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5776432 No 1998-07-07 2015-07-07 US 
US6446627 No 2002-09-10 2017-12-18 US US8132712 No 2012-03-13 2028-09-07 US US7780038 No 2010-08-24 2027-01-24 US US9463289 No 2016-10-11 2031-05-18 US US8931476 No 2015-01-13 2031-07-17 US US7637260 No 2009-12-29 2020-08-25 US US9808587 No 2017-11-07 2031-05-18 US US10022510 Yes 2018-07-17 2031-11-18 US US10022509 No 2018-07-17 2031-05-18 US US10086156 No 2018-10-02 2031-05-18 US US10188811 No 2019-01-29 2031-10-21 US US10561808 Yes 2020-02-18 2032-07-01 US US10695512 No 2020-06-30 2031-05-18 US US10792447 No 2020-10-06 2039-01-25 US US11395889 No 2011-05-18 2031-05-18 US US11395888 No 2018-01-26 2038-01-26 US US11559637 No 2019-07-21 2039-07-21 US US11583643 No 2021-08-19 2041-08-19 US US11793953 No 2018-01-26 2038-01-26 US US11865247 No 2018-01-26 2038-01-26 US US11896759 No 2018-01-26 2038-01-26 US US11957832 No 2021-05-05 2041-05-05 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 208-210 MSDS logP 3.49 MSDS - Predicted Properties
Property Value Source Water Solubility 0.00208 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 134.79 m3·mol-1 Chemaxon Polarizability 54.46 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9904 Blood Brain Barrier + 0.9851 Caco-2 permeable + 0.5698 P-glycoprotein substrate Substrate 0.7529 P-glycoprotein inhibitor I Inhibitor 0.5986 P-glycoprotein inhibitor II Non-inhibitor 0.7488 Renal organic cation transporter Non-inhibitor 0.7907 CYP450 2C9 substrate Non-substrate 0.8634 CYP450 2D6 substrate Non-substrate 0.9174 CYP450 3A4 substrate Substrate 0.784 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.7516 CYP450 2C19 inhibitor Non-inhibitor 0.9122 CYP450 3A4 inhibitor Non-inhibitor 0.7875 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8577 Ames test Non AMES toxic 0.938 Carcinogenicity Non-carcinogens 0.914 Biodegradation Not ready biodegradable 0.9932 Rat acute toxicity 2.1115 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9456 hERG inhibition (predictor II) Non-inhibitor 0.6054
Spectra
- Mass Spec (NIST)
- Download (11.1 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 229.3158221 predictedDarkChem Lite v0.1.0 [M-H]- 207.07243 predictedDeepCCS 1.0 (2019) [M+H]+ 230.2261221 predictedDarkChem Lite v0.1.0 [M+H]+ 209.02943 predictedDeepCCS 1.0 (2019) [M+Na]+ 229.3366221 predictedDarkChem Lite v0.1.0 [M+Na]+ 215.17845 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for glucocorticoids (GC) (PubMed:27120390, PubMed:37478846). 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 modulator of other transcription factors (PubMed:28139699). Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Involved in chromatin remodeling (PubMed:9590696). Plays a role in rapid mRNA degradation by binding to the 5' UTR of target mRNAs and interacting with PNRC2 in a ligand-dependent manner which recruits the RNA helicase UPF1 and the mRNA-decapping enzyme DCP1A, leading to RNA decay (PubMed:25775514). 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 (By similarity)
- Specific Function
- core promoter sequence-specific DNA binding
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Saklatvala J: Glucocorticoids: do we know how they work? Arthritis Res. 2002;4(3):146-50. Epub 2002 Jan 21. [Article]
- 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. [Article]
- 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. [Article]
- Wurthwein G, Rohdewald P: Activation of beclomethasone dipropionate by hydrolysis to beclomethasone-17-monopropionate. Biopharm Drug Dispos. 1990 Jul;11(5):381-94. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species
- Specific Function
- serine-type endopeptidase inhibitor activity
- Gene Name
- SERPINA6
- Uniprot ID
- P08185
- Uniprot Name
- Corticosteroid-binding globulin
- Molecular Weight
- 45140.49 Da
References
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Crowe A, Tan AM: Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. Toxicol Appl Pharmacol. 2012 May 1;260(3):294-302. doi: 10.1016/j.taap.2012.03.008. Epub 2012 Mar 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- Pavek P, Merino G, Wagenaar E, Bolscher E, Novotna M, Jonker JW, Schinkel AH: Human breast cancer resistance protein: interactions with steroid drugs, hormones, the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine, and transport of cimetidine. J Pharmacol Exp Ther. 2005 Jan;312(1):144-52. doi: 10.1124/jpet.104.073916. Epub 2004 Sep 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- de Graan AJ, Lancaster CS, Obaidat A, Hagenbuch B, Elens L, Friberg LE, de Bruijn P, Hu S, Gibson AA, Bruun GH, Corydon TJ, Mikkelsen TS, Walker AL, Du G, Loos WJ, van Schaik RH, Baker SD, Mathijssen RH, Sparreboom A: Influence of polymorphic OATP1B-type carriers on the disposition of docetaxel. Clin Cancer Res. 2012 Aug 15;18(16):4433-40. doi: 10.1158/1078-0432.CCR-12-0761. Epub 2012 Jun 18. [Article]
- Gui C, Obaidat A, Chaguturu R, Hagenbuch B: Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3. Curr Chem Genomics. 2010 Mar 1;4:1-8. doi: 10.2174/1875397301004010001. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10779507, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (17-beta-glucuronosyl estradiol, dehydroepiandrosterone sulfate (DHEAS), and estrone 3-sulfate), as well as eicosanoid leukotriene C4, prostaglandin E2 and L-thyroxine (T4) (PubMed:10779507, PubMed:11159893, PubMed:12568656, PubMed:15159445, PubMed:17412826, PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). Shows a pH-sensitive substrate specificity towards sulfated steroids, taurocholate and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Involved in the clearance of bile acids and organic anions from the liver (PubMed:22232210). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins) such as pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:15159445). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- de Graan AJ, Lancaster CS, Obaidat A, Hagenbuch B, Elens L, Friberg LE, de Bruijn P, Hu S, Gibson AA, Bruun GH, Corydon TJ, Mikkelsen TS, Walker AL, Du G, Loos WJ, van Schaik RH, Baker SD, Mathijssen RH, Sparreboom A: Influence of polymorphic OATP1B-type carriers on the disposition of docetaxel. Clin Cancer Res. 2012 Aug 15;18(16):4433-40. doi: 10.1158/1078-0432.CCR-12-0761. Epub 2012 Jun 18. [Article]
- Gui C, Obaidat A, Chaguturu R, Hagenbuch B: Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3. Curr Chem Genomics. 2010 Mar 1;4:1-8. doi: 10.2174/1875397301004010001. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 11, 2024 18:19