Beclometason

Bezeichnung:Beclometason

CAS-Nr4419-39-0

Englisch Name:BECLOMETHASONE

CBNumberCB7694093

SummenformelC22H29ClO5

Molgewicht408.92

MOL-Datei4419-39-0.mol

Synonyma

Beclometason

Beclometason physikalisch-chemischer Eigenschaften

Schmelzpunkt	217- 222°C (dec.)
Siedepunkt	600.2±55.0 °C(Predicted)
Dichte	1.35±0.1 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	Dioxane (Sparingly, Sonicated), DMSO (Sparingly), Ethyl Acetate (Slightly), Methane
Aggregatzustand	Solid
pka	12.17±0.70(Predicted)
Farbe	White to Pale Beige
Merck	13,1020
Stabilität	Hygroscopic
CAS Datenbank	4419-39-0(CAS DataBase Reference)

Sicherheit

S-Sätze:	24/25
WGK Germany	3
HS Code	29372900

Gefahreninformationscode (GHS)

BECLOMETHASONE Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Beclomethasone dipropionate is claimed to exert a topical effect on the lungs without significant systemic activity. It is used by inhalation, generally from a metered aerosol, for the prophylaxis of the symptoms of asthma.
Chemische Eigenschaften
White to Off-White Solid
Originator
Propaderm,Kyowa Hakko,Japan,1972
Verwenden
Beclomethasone has been used in MS?MS (mass spectrometry) methods for the analysis of β-agonists, corticosteroids, chloramphenicol and penicillins. It has also been used to find the differential response of glucocorticoids in larval regeneration model.
Verwenden
Glucocorticoid. Beclomethasone is used in chronic asthma and allergic rhinitis. Antiallergic, antiasthmatic (inhalant). Anti-inflammatory (topical).
Definition
ChEBI: A 17alpha-hydroxy steroid that is prednisolone in which the hydrogens at the 9alpha and 16beta positions are substituted by a chlorine and a methyl group, respectively.
Manufacturing Process
6 grams of 6β-methyl-1,4-pregnadiene-11β,17α,21-triol-3,20-dione-21-acetate is dissolved in a mixture of 35 ml of dimethylformamide and 6 ml of pyridine. To the resulting solution is added 2.5 ml of methanesulfonyl chloride and the reaction mixture maintained at 80°-85°C for about 1 hour. The resulting red solution is cooled in an ice bath and treated successively with 55 ml of methanol, 240 ml of 5% aqueous sodium bicarbonate and finally with 360 ml of water. The resulting reaction mixture is then allowed to stand at room temperature overnight after which the precipitated product is removed by filtration, washed repeatedly with water and dried to a constant weight in air at about 50°C to produce 6β-methyl-1,4,9(11)-pregnadiene-11α,21-diol-3,20- dione-21-acetate.
Hydrolysis of the acetate ester with alkali, e.g., sodium methoxide in methanol, affords the free alcohol, 16β-methyl-1,4,9(11)-pregnadiene-17α,21- diol-3,20-dione. To a suspension of 3 grams of 6β-methyl-1,4,9(11)- pregnadiene-17α,21-diol-3,20-dione-21-acetate 40 ml of acetone is added at 0°C with stirring 2 grams of N-chlorosuccinimide and then 7 ml of a perchloric acid solution prepared by dissolving 0.548 ml of 70% perchloric acid in 33 ml of water. The resulting reaction mixture is stirred at 0° for about 4 hours 45 minutes.
The excess of N-chlorosuccinimide is destroyed by the addition of about 15 drops of allyl alcohol and 180 ml of water is then added with stirring. This mixture is held at 0°C for about one hour. The precipitated 16β-methyl-1,4- pregnadiene-9α-chloro-11β,17α,21-triol-3,20-dione-21-acetate is recovered filtration. A solution of 250 mg of the chlorohydrin in 5 ml of 0.25N perchloric acid in methanol is stirred for about 18 hours at room temperature to produce 16β-methyl-9α-chloro-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione which is recovered by adding water to the reaction mixture and allowing the product to crystallize. Propionic anhydride is then used to convert this material to the dipropionate.
Trademarks
Beclovent (GlaxoSmithKline); Beconase (GlaxoSmithKline); Qvar (3M Pharmaceuticals); Vanceril (Schering).
Therapeutic Function
Topical antiinflammatory, Glucocorticoid
Biologische Funktion
The topical anti-inflammatory potency for beclomethasone dipropionate (BDP) is approximately 5,000 times greater than hydrocortisone, 500 times greater than betamethasone or dexamethasone, and approximately five times greater than fluocinolone acetonide or triamcinolone acetonide, as measured by vasoconstrictor assay.
Biochem/physiol Actions
Beclomethasone is an anti-inflammatory glucocorticoid.It helps to decrease airway hyperresponsiveness. It also helps to regulate symptoms of asthma.
Clinical Use
Beclomethasone, a 9α-chloro analogue of betamethasone, is a potent glucocorticoid with approximately half the potency of its fluoro analogue. It is used topically as its dipropionate derivative in inhalation aerosol therapy for asthma and rhinitis but not for treatment of steroid-responsive dermatoses.

BECLOMETHASONE Upstream-Materialien And Downstream Produkte

Beclometason Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

4419-39-0, BECLOMETHASONE Verwandte Suche:

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