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
5534-09-8Relevant 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
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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
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, (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.