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
Glucocorticoid. Beclomethasone is used in chronic asthma and allergic rhinitis. Antiallergic, antiasthmatic (inhalant). Anti-inflammatory (topical).
Uses
Beclomethasone has been used in MSMS (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.
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.
