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Beclomethasone Dipropionate

HCID 21700
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Grundinformationen

CAS
5534-09-8
Standard-SMILES
CCC(=O)OCC(=O)[C@@]1(OC(=O)CC)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@@]21C
InChIKey
KUVIULQEHSCUHY-XYWKZLDCSA-N
Summenformel
C28H37ClO7
Durchschnittliche Molmasse
521 g/mol
Monoisotopische Masse
520,2227812

Namen und Bezeichner

Bevorzugter Name
Beclomethasone Dipropionate
IUPAC
[2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate

Namen und Synonyme

BECLOMETHASONE DIPROPIONATEBeclometasone dipropionate5534-09-8BecloventVancenaseSanasthmaxAerobecBeclacinBeclometBecotideEntydermaKorbutone
Weitere Namen anzeigen
PropadermVancerilQvarBecloforteSanasthmylViaroxPropaderm ForteRino-clenil

Datenbank-Bezeichner

CAS
5534-09-8
PubChem CID
21700
DTXSID
DTXSID3048730
ChEMBL
CHEMBL1200500
ChEBI
CHEBI:3002
UNII
5B307S63B2
EC Number
226-886-0
Nikkaji
J7.992H

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3
Polarare Oberfläche (TPSA)
107 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
8
Schwere Atome
36
Formalladung
0
Komplexität
1.050

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

3.49

1.3

Solubility2.08e-03 g/L
Melting Point · 2 Einträge

208-210

117 - 120 °C

Physical DescriptionSolid

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

Danger

H360 (76.4%): May damage fertility or the unborn child [Danger Reproductive toxicity];H361fd (16.4%): Suspected of damaging fertility; Suspected of damaging the unborn child [Warning Reproductive toxicity];H373 (53.6%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P203, P260, P280, P318, P319, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 110 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Hazard Traits - Developmental Toxicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product

Beclomethasone dipropionate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 1 Eintrag

IMAP assessments - Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11.beta.,16.beta.)-: Environment tier I assessment;IMAP assessments - Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11.beta.,16.beta.)-: Human health tier I assessment

Hazard Classes and CategoriesRepr. 1B (76.4%);Repr. 2 (16.4%);STOT RE 2 (53.6%)

Chemie und Industrie

Pharmakologische Informationen

Protein BindingBased 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.
Pharmacodynamics · 1 Eintrag

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. Beclomethasone dipropionate is reported to exhibit potent topical activity while possessing low systemic effects. 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. 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. It was shown to suppress the hypothalamo-pituitary-adrenal (HPA) axis in a dose-dependent manner. HPA axis is a central hormonal response system to stress and activation of HPA axis leads to the production of endogenous steroid hormone production. Long-term use of high-dose systemic

Mechanism of Action · 1 Eintrag

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. 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. 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. 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. 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. 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.

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Regulatorische Informationen

Regulatory Information · 2 Einträge

Hazard Traits - Developmental Toxicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product

Beclomethasone dipropionate: Does not have an individual approval but may be used under an appropriate group standard

Biological Half-Life · 1 Eintrag

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.

Metabolism/Metabolites · 1 Eintrag

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. About 95% of the total beclomethasone dipropionate administered via oral inhalation undergoes presystemic conversion to form 17-BMP in the lung.

FDA Pharmacological Classification · 4 Einträge

BECLOMETHASONE DIPROPIONATE

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

BECLOMETHASONE DIPROPIONATE HFA

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

MeSH Pharmacological Classification · 3 Einträge

Substances that reduce or suppress INFLAMMATION.

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.

Drugs that are used to treat asthma.

Absorption, Distribution and Excretion · 4 Einträge

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. 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.

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.

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.

Following intravenous administration, the clearance of beclomethasone dipropionate and 17-BMP were 150 L/h and 120 L/h, respectively.

Cellular LocationsCytoplasm;Extracellular;Membrane

Anbieter21 Anbieter

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