Beclomethasone dipropionate
- Product Name
- Beclomethasone dipropionate
- CAS No.
- 5534-09-8
- Chemical Name
- Beclomethasone dipropionate
- Synonyms
- BECLOMETASONE DIPROPIONATE;Dipropionate;becotide;vanceril;Beconase;beclovent;vancenase;Beclotide;Beconase AQ;Beclomethasone propionate
- CBNumber
- CB4376831
- Molecular Formula
- C28H37ClO7
- Formula Weight
- 521.04
- MOL File
- 5534-09-8.mol
Beclomethasone dipropionate Property
- 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
- solubility
- Chloroform (Slightly), Dioxane (Slightly, Sonicated), Methanol (Slightly, Heated
- form
- Solid
- pka
- 13.02±0.70(Predicted)
- color
- White
- λmax
- 238nm(EtOH)(lit.)
- Merck
- 14,1019
- InChIKey
- KUVIULQEHSCUHY-NHOFSDNKNA-N
- SMILES
- [C@@]1(OC(=O)CC)(C(=O)COC(=O)CC)[C@@H](C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]12C |&1:0,14,17,19,29,31,33,36,r|
- CAS DataBase Reference
- 5534-09-8(CAS DataBase Reference)
Safety
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
H350May cause cancer
H360May damage fertility or the unborn child
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- Y0000469
- Product name
- Beclometasone dipropionate for peak identification
- Purity
- European Pharmacopoeia (EP) Reference Standard
- Packaging
- Y0000469
- Price
- $153
- Updated
- 2024/03/01
- Product number
- PHR1619
- Product name
- Beclomethasone Dipropionate
- Purity
- Pharmaceutical Secondary Standard; Certified Reference Material
- Packaging
- 1G
- Price
- $121
- Updated
- 2024/03/01
- Product number
- B3022
- Product name
- Beclomethasone dipropionate
- Purity
- analytical standard, for drug analysis
- Packaging
- 250MG
- Price
- $74.1
- Updated
- 2024/03/01
- Product number
- BP030
- Product name
- Beclometasone (beclomethasone) dipropionate
- Purity
- British Pharmacopoeia (BP) Assay Standard
- Packaging
- 100MG
- Price
- $223
- Updated
- 2024/03/01
- Product number
- B3022
- Product name
- Beclomethasone dipropionate
- Purity
- analytical standard, for drug analysis
- Packaging
- 1G
- Price
- $241
- Updated
- 2024/03/01
Beclomethasone dipropionate Chemical Properties,Usage,Production
Chemical Properties
The light yellow solid has low solubility in water, but high solubility in chloroform. It can easily dissolve in acetone and ethanol.
Originator
Propaderm,Kyowa Hakko,Japan,1972
Uses
Beclomethasone dipropionate is a topically active corticosteroid used as an adjuvant in the control of chronic asthma when given by inhalation as an aerosol. It is also used as a topical anti-inflammatory.
Definition
ChEBI: Beclomethasone dipropionate is a steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions. It has a role as an anti-inflammatory drug, an anti-asthmatic drug, a prodrug and an anti-arrhythmia drug. It is a steroid ester, an enone, a 20-oxo steroid, an 11beta-hydroxy steroid, a propanoate ester, a corticosteroid, a glucocorticoid, a 3-oxo-Delta(1),Delta(4)-steroid and a chlorinated steroid. It is functionally related to a beclomethasone.
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
Beclomethasone dipropionate (Beclovent, Beconase, Vanceril, Vancenase) (BDP) is rapidly converted in the lungs to beclomethasone 17-monopropionate (17-BMP), the metabolite that provides the bulk of the anti-inflammatory activity. The monopropionate also has a higher affinity for the GR than either the dipropionate or beclomethasone. The portion of BDP that is swallowed is rapidly hydrolyzed to 17-BMP, 21-BMP (which arises by a transesterification reaction from 17-BMP), and beclomethasone itself. Beclomethasone has much less GC activity than the monopropionate. It is used in nasal sprays and aerosol formulations totreat allergic rhinitis and asthma.
Biological Activity
beclomethasone dipropionate(bdp) is a topically active and anti-inflammatory corticosteroid used in treatment of asthma and rhinitis [1].beclomethasone dipropionate(bdp) is a topically active and anti-inflammatory corticosteroid used in treatment of asthma and rhinitis. in addition, beclomethasone dipropionate has been reported to be previously developed as aqueous nasal formulations for the treatment of allergic rhinitis. moreover, beclomethasone dipropionate has shown the availability in dry nasal aerosol formulations as chiorofluoro carbon metered-dose inhaler nasal sprays [1].
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.
Mode of action
Beclomethasone dipropionate works by attenuating the inflammatory responses associated with asthma, allergic rhinitis, nasal polyps, and corticosteroid-responsive dermatoses. It suppresses the actions of inflammatory cells, such as mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils.
References
[1] PAUL H. RATNER MD . Pharmacokinetic Profile of Beclomethasone Dipropionate Hydrofluoroalkane After Intranasal Administration Versus Oral Inhalation in Healthy Subjects: Results of a Single-Dose, Randomized, Open-Label, 3-Period Crossover Study[J]. Clinical therapeutics, 2012, 34 6: Pages 1422-1431. DOI:10.1016/j.clinthera.2012.04.023.
[2] R N BROGDEN. Beclomethasone dipropionate inhaler: a review of its pharmacology, therapeutic value and adverse effects. I: Asthma.[J]. Drugs, 1975, 10 3: 166-210. DOI:10.2165/00003495-197510030-00002.
[3] P. DALEY-YATES. Beclomethasone dipropionate: absolute bioavailability, pharmacokinetics and metabolism following intravenous, oral, intranasal and inhaled administration in man.[J]. British journal of clinical pharmacology, 2001, 51 5 1: 400-409. DOI:10.1046/J.0306-5251.2001.01374.X.
[4] https://go.drugbank.com/drugs/DB00394
[5] https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020911s029s030lbl.pdf
Beclomethasone dipropionate Preparation Products And Raw materials
Raw materials
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View Lastest Price from Beclomethasone dipropionate manufacturers
- Product
- Beclomethasone dipropionate 5534-09-8
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 5000
- Release date
- 2023-07-27
- Product
- Beclomethasone dipropionate 5534-09-8
- Price
- US $0.00/KG
- Min. Order
- 100g
- Purity
- 97%-103%;USP
- Supply Ability
- 10KGS
- Release date
- 2021-07-09
- Product
- Beclomethasone dipropionate 5534-09-8
- Price
- US $2200.00/kg
- Min. Order
- 1kg
- Purity
- 99% HPLC
- Supply Ability
- 20 tons
- Release date
- 2022-10-20