BECLOMETHASONE Chemical Properties

Melting point:

217- 222°C (dec.)

Boiling point:

600.2±55.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Dioxane (Sparingly, Sonicated), DMSO (Sparingly), Ethyl Acetate (Slightly), Methane

form 

Solid

pka

12.17±0.70(Predicted)

color 

White to Pale Beige

Merck 

13,1020

Stability:

Hygroscopic

CAS DataBase Reference

4419-39-0(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29372900

MSDS

• Language:English Provider:SigmaAldrich

BECLOMETHASONE Usage And Synthesis

Description

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.

Chemical Properties

White to Off-White Solid

Originator

Propaderm,Kyowa Hakko,Japan,1972

Uses

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.

Uses

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.

brand name

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

Therapeutic Function

Topical antiinflammatory, Glucocorticoid

Biological Functions

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.

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