Beclometasone dipropionate

from Wikipedia, the free encyclopedia
Structural formula
Beclometasone 17.21 dipropionate
General
Non-proprietary name Beclometasone
other names
  • Beclometasone 17.21 dipropionate
  • 9-chloro-11 β , 17,21-trihydroxy-16 β -methylpregna-1,4-diene-3,20-dione 17,21-dipropionate
Molecular formula C 28 H 37 ClO 7
External identifiers / databases
CAS number 5534-09-8
EC number 226-886-0
ECHA InfoCard 100,024,442
PubChem 21700
ChemSpider 20396
DrugBank DB00394
Wikidata Q421475
Drug information
ATC code

A07 EA07 , D07 AC15 , R01 AD01 , R03 BA01

Drug class
properties
Molar mass 520.22 g · mol -1
Physical state

firmly

Melting point

212 ° C (decomposition)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
08 - Dangerous to health

danger

H and P phrases H: 360
P: 201-308 + 313
Toxicological data

> 3750 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Beclometasone dipropionate ( INN : beclometasone ) is a synthetic glucocorticoid with anti-inflammatory and vasoconstricting properties. It is used as a medicinal substance for the topical treatment of asthma , allergic rhinitis, and sinusitis .

Chemically, it is the propionic acid ester of the free alcohol beclometasone (9 α -chloro-16 β -methylprednisolone; 9 α -chloro-11 β , 17 α , 21-trihydroxy-16 β -methylpregna-1,4-diene- 3,20-dione).

Pharmacokinetic properties

Structure of beclometasone

Beclometasone 17.21 dipropionate has been used since 1972. It is a prodrug : After hydrolysis by esterases , the active metabolite beclomethasone-17-monopropionate is formed. In the liver, this is further converted into pharmacologically inactive metabolites such as beclomethasone-21-monopropionate and beclomethasone (free alcohol) by means of the first-pass effect . This limits systemic bioavailability and toxicity.

effect

Beclometasone dipropionate has anti-inflammatory , immunosuppressive and antiallergic effects . It is therefore used to treat asthmatic forms of illness and breathing difficulties. The full effect only occurs after a few hours or days.

In pregnancy beclomethasone dipropionate should be taken only on prescription, and after an intensive risk-benefit analysis. Because in newborns with mothers who took this active ingredient during pregnancy, occasional damage to the adrenal function was found. During breastfeeding , the active ingredient should also only be taken on a doctor's prescription, as beclometasone is transferred to the baby through breast milk .

Trade names

Monopreparations

Aerocortin (A), BECeco (CH), Beclorhinol, Beconase (D, CH), Bronchocort (D), Cyclocaps (D), Douglan (A), Junik (D), Livocab TM (D), Qvar (A, CH ), RatioAllerg (D), Rhinivict (D), Sanasthmax (D), Sanasthmyl (D), Ventolair (D), Clenil-Spray (I), numerous generics (D, A)

Combination preparations

Combination preparations with formoterol : Formodual (A), Foster (D, A), Inuvair (D)

literature

  • Peter T. Daley-Yates et al. (2001): Beclomethasone dipropionate: absolute bioavailability, pharmacokinetics and metabolism following intravenous, oral, intranasal and inhaled administration in man. In: Br. J. Clin. Pharmacol. 51 (5): pp. 400-409. PMID 11421996 doi: 10.1046 / j.0306-5251.2001.01374.x

Individual evidence

  1. ↑ Entry on beclometasone. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
  2. ↑ a b Datasheet Beclomethasone dipropionate from Sigma-Aldrich , accessed on November 4, 2016 ( PDF ).
  3. ↑ Beclometasone data sheet (PDF) at EDQM , accessed on September 1, 2008.
  4. ↑ a b External identifiers or database links to beclometasone : CAS number: 4419-39-0, EC number: 224-585-9, ECHA InfoCard: 100.022.352 , PubChem : 20469 , Wikidata : Q31948091 .
  5. ↑ Beclometasone in pregnancy. Archived from the original on December 5, 2018 ; accessed on June 27, 2017 .