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Beclomethasone dipropionate

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Beclomethasone dipropionate Basic information

Product Name:
Beclomethasone dipropionate
Synonyms:
  • 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
CAS:
5534-09-8
MF:
C28H37ClO7
MW:
521.04
EINECS:
226-886-0
Product Categories:
  • BECLOVENT
  • Intermediates & Fine Chemicals
  • Active Pharmaceutical Ingredients
  • Pharmaceuticals
  • Steroids
  • Intracellular receptor
Mol File:
5534-09-8.mol
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Beclomethasone dipropionate Chemical Properties

Melting point:
117-120 C
alpha 
D +98.0° (c = 1.0 in dioxane)
Boiling point:
613.3°C (rough estimate)
Density 
1.0766 (rough estimate)
refractive index 
1.4429 (estimate)
storage temp. 
Sealed in dry,2-8°C
pka
13.02±0.70(Predicted)
λmax
238nm(EtOH)(lit.)
Merck 
14,1019
CAS DataBase Reference
5534-09-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
T,Xn
Risk Statements 
60-61-36/37/38-20/21/22
Safety Statements 
53-36/37/39-45-36-26
WGK Germany 
3
RTECS 
TU3805000
HS Code 
29372100
Toxicity
LD50 oral in rat: > 3750mg/kg

MSDS

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Beclomethasone dipropionate Usage And Synthesis

Chemical Properties

Light Yellow Solid

Originator

Propaderm,Kyowa Hakko,Japan,1972

Uses

Antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical)

Uses

antiasthmatic, topical antiinflammatory

Uses

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.

brand name

Beclovent (GlaxoSmithKline); Beconase (GlaxoSmithKline); Qvar (3M Pharmaceuticals); Vanceril (Schering).

Therapeutic Function

Topical antiinflammatory, Glucocorticoid

Biological Functions

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).

General Description

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.

General Description

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.

Side effects

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.

Metabolism

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.

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