| Identification | More | [Name]
Beclomethasone dipropionate | [CAS]
5534-09-8 | [Synonyms]
aldecin
BECLOMETASONE DIPROPIONATE
BECLOMETHASONE 17-ALPHA,21-DIPROPIONATE
BECLOMETHASONE DIPROPIONATE
17,21-dipropionate
9-chloro-16-beta-methyl-11-beta,17,21-trihydroxy-pregna-1-4-diene-20-dione
beclacin
becloforte
beclometasone17,21-dipropionate
becloval
beclovent
becotide
benconase
bp2
clenil-a
dipropionatebeclomethasone
entyderma
| [EINECS(EC#)]
226-886-0 | [Molecular Formula]
C34H49ClO11 | [MDL Number]
MFCD00135613 | [Molecular Weight]
669.2 | [MOL File]
5534-09-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Solid | [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. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Dioxane (Slightly, Sonicated), Methanol (Slightly, Heated | [form ]
Solid | [pka]
13.02±0.70(Predicted) | [color ]
White | [Usage]
Antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical) | [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 Data | Back Directory | [Hazard Codes ]
T,Xn | [Risk Statements ]
R60:May impair fertility.
R61:May cause harm to the unborn child.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
TU3805000
| [HS Code ]
2937220000 | [Toxicity]
LD50 oral in rat: > 3750mg/kg |
| Hazard Information | Back Directory | [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[5534-09-8] 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]
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. | [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 |
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