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5534-09-8

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5534-09-8 Usage

Chemical Properties

Light Yellow Solid

Uses

Different sources of media describe the Uses of 5534-09-8 differently. You can refer to the following data:
1. Antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical)
2. Beclomethasone Dipropionate (Betamethasone Dipropionate EP Impurity E) is an antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical).
3. antiasthmatic, topical antiinflammatory
4. Anti-arrhythmia Agent, corticosteroids

Definition

ChEBI: A steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions.

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

Different sources of media describe the General Description of 5534-09-8 differently. You can refer to the following data:
1. 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.
2. 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.

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.

references

[1] ratner ph1, melchior a, dunbar sa, tantry sk, dorinsky pm. 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. clin ther. 2012 jun;34(6):1422-31.

Check Digit Verification of cas no

The CAS Registry Mumber 5534-09-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,3 and 4 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5534-09:
(6*5)+(5*5)+(4*3)+(3*4)+(2*0)+(1*9)=88
88 % 10 = 8
So 5534-09-8 is a valid CAS Registry Number.
InChI:InChI=1/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20?,21-,25-,26-,27?,28-/m0/s1

5534-09-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B4464)  Beclometasone Dipropionate  >98.0%(HPLC)

  • 5534-09-8

  • 1g

  • 690.00CNY

  • Detail
  • TCI America

  • (B4464)  Beclometasone Dipropionate  >98.0%(HPLC)

  • 5534-09-8

  • 5g

  • 1,450.00CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1619)  Beclomethasone Dipropionate  pharmaceutical secondary standard, traceable to USP, PhEur, BP

  • 5534-09-8

  • PHR1619-1G

  • 958.23CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000469)  Beclometasone dipropionate for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 5534-09-8

  • Y0000469

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000352)  Beclometasone dipropionate for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 5534-09-8

  • Y0000352

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (B0305000)  Beclomethasonedipropionate  anhydrous, European Pharmacopoeia (EP) Reference Standard

  • 5534-09-8

  • B0305000

  • 1,880.19CNY

  • Detail
  • USP

  • (1048506)  Beclomethasonedipropionate  United States Pharmacopeia (USP) Reference Standard

  • 5534-09-8

  • 1048506-200MG

  • 4,662.45CNY

  • Detail

5534-09-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name beclomethasone dipropionate

1.2 Other means of identification

Product number -
Other names Beclomethasone Dipropionate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5534-09-8 SDS

5534-09-8Synthetic route

beclomethasone 11,17,21-tripropionate

beclomethasone 11,17,21-tripropionate

beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

Conditions
ConditionsYield
With gluconic acid In water at 0℃; Reagent/catalyst; Temperature;99.2%
With gluconic acid In tetrahydrofuran at 0℃; for 1h; Reagent/catalyst; Solvent; Temperature;
C28H36O7

C28H36O7

beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate at 0℃; for 5.5h; Temperature;24.8 g
9β, 11β-epoxy-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

9β, 11β-epoxy-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

ethyl acetate n-hexane

ethyl acetate n-hexane

beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

16β-methyl-21-propionyloxy-1,4,16-pregnatriene-3,11,20-trione
79884-51-8

16β-methyl-21-propionyloxy-1,4,16-pregnatriene-3,11,20-trione

Conditions
ConditionsYield
With nitrogen92%
beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

A

21-beclomethasone monopropionate

21-beclomethasone monopropionate

B

beclomethasone 17-monopropionate
5534-18-9

beclomethasone 17-monopropionate

Conditions
ConditionsYield
In various solvent(s) at 37℃; for 18h; Kinetics; Product distribution; Hydrolysis;
beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

9α-Chloro-11β,17α,21-trihydroxy-16β-methyl-5β-pregnane-3,20-dione 17,21-dipropionate
80163-95-7

9α-Chloro-11β,17α,21-trihydroxy-16β-methyl-5β-pregnane-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
p-TSA; palladium In 4,4-dichlorobutan-2-one; ethyl acetate
p-TSA; palladium In 4,4-dichlorobutan-2-one; ethyl acetate
beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

A

betamethasone 9,11-epoxide 17,21-dipropionate
66917-44-0

betamethasone 9,11-epoxide 17,21-dipropionate

B

C22H26O4

C22H26O4

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile at 20℃; for 0.333333h; Mattox rearrangement;
beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

beclomethasone
4419-39-0, 4647-20-5

beclomethasone

Conditions
ConditionsYield
With potassium hydrogencarbonate In methanol at 20℃; for 72h;
beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

(8S,9R,10S,11S,13S,14S,16S,17R)-9-Chloro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid
37927-35-8

(8S,9R,10S,11S,13S,14S,16S,17R)-9-Chloro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydrogencarbonate / methanol / 72 h / 20 °C
2: 1,4-dioxane; water / 48 h / 20 °C
View Scheme
beclomethasone 17,21-dipropionate
5534-09-8

beclomethasone 17,21-dipropionate

C38H45ClN4O5*ClH

C38H45ClN4O5*ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydrogencarbonate / methanol / 72 h / 20 °C
2: 1,4-dioxane; water / 48 h / 20 °C
3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 24 h / 20 °C
View Scheme

5534-09-8Relevant articles and documents

Practical and scalable synthesis of beclomethasone dipropionate

Welideniya, Dhanushi T.,Jayathilaka, Adeesha S.,Acharige, Anjana Delpe,Samanthi,Wanninayake, Umayangani K.,Perera, Shashika S.,Rajapaksha, Weranga,Fernando, Chamod C.,Hewadikaram, Madhavi,Buddhika, Janani,Gunasekara, Pivini,Karunaratne, Veranja,Amaratunga,Gunasekera, Dinara S.

, (2021/12/22)

Beclomethasone dipropionate (1) is a synthetic corticosteroid with anti-inflammatory, antipruritic, and anti-allergy properties. It is widely used to treat asthma, allergic rhinitis, and dermatoses. However, existing synthetic routes to this active pharmaceutical ingredient (API) contain steps resulting in low and/or inconsistent yields, and use obsolete reagents. Such inconsistencies coupled with a lack of reliable experimental data makes laboratory-scale and large-scale synthesis of this API difficult and time-consuming. In this paper, we report a practical and scalable approach to synthesize 1 from the readily available steroidal intermediate, 16β-methyl epoxide (3, DB-11). A gram-scale to kilogram-scale synthesis of 1 was achieved with 82% yield, using a cost-effective and scalable methodology. Selective propionylation of the hydroxyl groups at C17 and C21 demonstrate the fact that this approach can be conveniently implemented in fine chemical industries.

A dipropionate double-c ester synthesis method free of organic solvents

-

Paragraph 0041; 0042; 0044; 0045; 0046; 0048-0050; 0053, (2018/09/26)

The invention relates to a synthetic method of a beclomethasone dipropionate organic-free solvent. According to the method, beclomethasone 11, 17, 21-tripropionate is taken as the raw material and reacts in an organic solvent with a gluconic acid solution or an aqueous solution of ester capable of being converted into gluconic acid in water to prepare the beclomethasone dipropionate organic-free solvent.

Aerosol formulations containing P134a and particulate medicaments

-

, (2008/06/13)

This invention relates to a pharmaceutical aerosol formulation containing a particulate medicament which is salmeterol or a physiologically acceptable salt or solvate thereof end 1,1,1,2-tetrafluoroethane as propellant, which formulation is free of surfactant or has less than 0.0001 % w/w surfactant based on the weight of medicament. The formulation may contain a further particulate medicament which is salbutamol, beclomethasone dipropionate or a physiologically acceptable salt or solvate thereof. A method of treating respiratory disorders which comprises administration by inhalation of an effective amount of the pharmaceutical aerosol formulation is also described.

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