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
- Molecular Weight:
- 521.04
- MOL File:
- 5534-09-8.mol
- Modify Date:
- 2024/5/1 11:53:09
| 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
Risk and Safety Statements
| Symbol(GHS) |   GHS07 ,GHS08 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H335-H350-H360 |
| Precautionary statements | P261-P305+P351+P338 |
| 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 |
Beclomethasone dipropionate price More Price(2)
Beclomethasone dipropionate Chemical Properties,Uses,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.
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.
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.
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
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Halcyon Labs Pvt. Ltd | +919833750169 | Mumbai, India | 17 | 58 | Inquiry |
| Enzal Chemicals India Limited | +91-9930897773 +91-9930897773 | New Delhi, India | 25 | 58 | Inquiry |
| Anant Pharmaceuticals Pvt Ltd | +91-8550986868 +91-9485998001 | Haryana, India | 461 | 58 | Inquiry |
| SynThink RESEARCH CHEMICALS | +91-8177860948 +91-8177860948 | Mumbai, India | 494 | 58 | Inquiry |
| Stermone Chemicals Pvt Ltd | +91-9328939700 +91-9328939700 | Gujarat, India | 20 | 58 | Inquiry |
| Maharshi Pharma Chem | +91-7940359347 +91-7433927173 | Gujarat, India | 24 | 58 | Inquiry |
| Prachem Laboratories | +91-7948993109 +91-7383072020 | Gujarat, India | 44 | 58 | Inquiry |
| Envee Drugs Pvt Ltd | +91-02682559595 +91-8866665858 | Gujarat, India | 36 | 58 | Inquiry |
| Ralington Pharma | +91-7948911722 +91-9687771722 | Gujarat, India | 1350 | 58 | Inquiry |
| Cipla Ltd | +912224826000 | Maharashtra, India | 133 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| Halcyon Labs Pvt. Ltd | 58 |
| Enzal Chemicals India Limited | 58 |
| Anant Pharmaceuticals Pvt Ltd | 58 |
| SynThink RESEARCH CHEMICALS | 58 |
| Stermone Chemicals Pvt Ltd | 58 |
| Maharshi Pharma Chem | 58 |
| Prachem Laboratories | 58 |
| Envee Drugs Pvt Ltd | 58 |
| Ralington Pharma | 58 |
| Cipla Ltd | 58 |
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