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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
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0000469
Product name
Beclometasone dipropionate for peak identification
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
Y0000469
Price
$153
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR1619
Product name
Beclomethasone Dipropionate
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1G
Price
$121
Updated
2024/03/01
Sigma-Aldrich
Product number
B3022
Product name
Beclomethasone dipropionate
Purity
analytical standard, for drug analysis
Packaging
250MG
Price
$74.1
Updated
2024/03/01
Sigma-Aldrich
Product number
BP030
Product name
Beclometasone (beclomethasone) dipropionate
Purity
British Pharmacopoeia (BP) Assay Standard
Packaging
100MG
Price
$223
Updated
2024/03/01
Sigma-Aldrich
Product number
B3022
Product name
Beclomethasone dipropionate
Purity
analytical standard, for drug analysis
Packaging
1G
Price
$241
Updated
2024/03/01
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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

Preparation Products

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Beclomethasone dipropionate Suppliers

Wuhan Zenuo Biopharmaceutical Technology Co., Ltd
Tel
027-87781970 15172508891
Email
1505560767@qq.com
Country
China
ProdList
133
Advantage
58
WUHAN MEIAN BIOMEDICINE TECHNOLOGY Co., Ltd,
Tel
15377551262
Email
180953430@qq.com
Country
China
ProdList
166
Advantage
58
Hubei Shiteng Chemical Technology Co. LTD
Tel
189-71839113 18971850150
Email
1273131441@qq.com
Country
China
ProdList
4989
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3572
Advantage
66
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19179
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
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View Lastest Price from Beclomethasone dipropionate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
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
Wuhan Haorong Biotechnology Co.,Ltd
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
Wuhan Senwayer Century Chemical Co.,Ltd
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

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