9-Chlor-11β-hydroxy-16β-methylpregna-1,4-dien-3,20-dion-17,21-dipropionat Produkt Beschreibung

Beclomethasone dipropionate Struktur
5534-09-8
  • CAS-Nr.5534-09-8
  • Bezeichnung:9-Chlor-11β-hydroxy-16β-methylpregna-1,4-dien-3,20-dion-17,21-dipropionat
  • Englisch Name:Beclomethasone dipropionate
  • Synonyma:9-Chlor-11β-hydroxy-16β-methylpregna-1,4-dien-3,20-dion-17,21-dipropionat
    bp2;QVAR;kw-053;Viarex;Viarox;Aerobec;Anceron;Beclate;aldecin;clenil-a
  • CBNumber:CB4376831
  • Summenformel:C28H37ClO7
  • Molgewicht:521.04
  • MOL-Datei:5534-09-8.mol
9-Chlor-11β-hydroxy-16β-methylpregna-1,4-dien-3,20-dion-17,21-dipropionat physikalisch-chemischer Eigenschaften
  • Schmelzpunkt: :117-120 C
  • alpha  :D +98.0° (c = 1.0 in dioxane)
  • Siedepunkt: :613.3°C (rough estimate)
  • Dichte :1.0766 (rough estimate)
  • Brechungsindex :1.4429 (estimate)
  • storage temp.  :Sealed in dry,2-8°C
  • pka :13.02±0.70(Predicted)
  • maximale Wellenlänge (λmax) :238nm(EtOH)(lit.)
  • Merck  :14,1019
  • CAS Datenbank :5534-09-8(CAS DataBase Reference)
Sicherheit

Beclomethasone dipropionate Chemische Eigenschaften,Einsatz,Produktion Methoden

  • R-Sätze Betriebsanweisung: R60:Kann die Fortpflanzungsfähigkeit beeinträchtigen.
    R61:Kann das Kind im Mutterleib schädigen.
    R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
    R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
  • S-Sätze Betriebsanweisung: S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
    S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
    S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
    S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
    S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  • Chemische Eigenschaften Light Yellow Solid
  • Originator Propaderm,Kyowa Hakko,Japan,1972
  • Verwenden Antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical)
  • Verwenden antiasthmatic, topical antiinflammatory
  • Verwenden Anti-arrhythmia Agent, corticosteroids
  • Definition ChEBI: A steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions.
  • 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 Beclomethasone dipropionate is used primarily as an inhalation aerosol therapy for asthma and rhinitis. A breakthrough in the discovery of new inhalation corticosteroids with reduced risks from systemic absorption was that the 17α-monopropionate ester of beclomethasone (17-BMP) was more active than BDP and 21-monopropionate (21-BMP) esters. Thus, BDP is a pro-drug that is rapidly metabolized by esterases in the lung and other tissues to its more active metabolite, 17-BMP, which has 30 times greater affinity for the GR than BDP and approximately 14 times dexamethasone (Table 33.5).
  • Allgemeine Beschreibung Beclomethasonedipropionate (Beclovent, Beconase, Vanceril, Vancenase)(BDP) is rapidly converted in the lungs to beclomethasone17-monopropionate (17-BMP), the metabolite that providesthe bulk of the anti-inflammatory activity. The monopropionatealso has higher affinity for the GR than either thedipropionate or beclomethasone. The portion of BDP that isswallowed is rapidly hydrolyzed to 17-BMP, 21-BMP(which arises by a transesterification reaction from 17-BMP), and beclomethasone itself. Beclomethasone hasmuch less GC activity than the monopropionate.
  • Allgemeine Beschreibung Beclomethasonedipropionate, 9-chloro-11β-hydroxy-16β-methyl-17,21-bis-(1-oxopropoxy)-pregna-1,4-diene-3,20-dione (Beconase,QVAR), is used in nasal sprays and aerosol formulations totreat allergic rhinitis and asthma.
  • Clinical Use Beclomethasone dipropionate is a lipophilic prodrug that, when inhaled, shows a systemic bioavailability of approximately 20% of the administered dose. The 16β-methyl group decreases mineralocorticoid activity, and the 9α-chloro group increases both the glucocorticoid and mineralocorticoid activity, resulting in potent anti-inflammatory activity with little or no salt-retaining effects.
  • Nebenwirkungen The main adverse effects are headache, sinusitis, and pain. Beclomethasone dipropionate is metabolized to the more active 17α-monopropionate derivative during absorption from the lungs and then further metabolized to the free alcohol in the liver.
  • Stoffwechsel The dipropionate also is metabolized to the inactive 21-monopropionate in the liver. Beclomethasone dipropionate and its metabolites are mainly excreted in the feces, with less than 10% excreted in the urine.
Beclomethasone dipropionate Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
9-Chlor-11β-hydroxy-16β-methylpregna-1,4-dien-3,20-dion-17,21-dipropionat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
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5534-09-8, Beclomethasone dipropionate Verwandte Suche:
  • 9-chloro-16-beta-methyl-11-beta,17,21-trihydroxy-pregna-1-4-diene-20-dione
  • beclacin
  • becloforte
  • beclometasone17,21-dipropionate
  • becloval
  • beclovent
  • becotide
  • benconase
  • bp2
  • clenil-a
  • dipropionatebeclomethasone
  • entyderma
  • inaloneo
  • inaloner
  • korbutone
  • kw-053
  • propaderm
  • propadermforte
  • rino-clenil
  • sanasthymyl
  • sch18020w
  • vancenase
  • vanceril
  • Beclometasone Dipropionate Imp.(EP)
  • BECLOMETHASONE DIPROPIONATE USP STANDARD
  • BECLOMETHASONE DIPROPIONATE USP(CRM STANDARD)
  • Pregna-1,4-Diene-3,20-Dione,9-Chloro-11-Hydroxy-16-Methyl-17,21-Bis(1-Oxopropoxy)-,(11Beta,16Beta)-
  • Beclomethasone-17,21-dipropionate
  • 9-chloro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate
  • CHEMBANK1430
  • 9α-Chloro-16β-methylprednisolone 17,21-dipropionate
  • Aerobec
  • Aldecin AQ nasal
  • Anceron
  • Beclate
  • Beclazone
  • Beclazone 250
  • Beclazone 50
  • Beclomet
  • Beclotide
  • Beclotide 100
  • Beclovent Inhaler
  • Becodisks
  • Beconase
  • Beconase AQ
  • Belchlorhinol
  • Belcoforte
  • Belcomet
  • Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11β,16β)-
  • Pregna-1,4-diene-3,20-dione, 9-chloro-11β,17,21-trihydroxy-16β-methyl-, 17,21-dipropionate (7CI, 8CI)
  • QVAR
  • Sanasthmax
  • Sanasthmyl
  • Sch 8020W
  • Vancenase AQ
  • 17,21-dipropionate
  • 9-Chloro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione (Beclometasone)
  • Dipropionate