| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
The primary target of beclomethasone 17-propionate is the glucocorticoid receptor (GR), a nuclear receptor that regulates gene expression. Upon binding to GR, the complex translocates to the nucleus where it binds to glucocorticoid response elements (GREs) to regulate transcription of anti-inflammatory and pro-inflammatory genes. The compound has 13-fold higher receptor affinity compared to its parent prodrug beclomethasone dipropionate, making it a highly potent glucocorticoid agonist.
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| ln Vitro |
Beclomethasone dipropionate metabolism to 17-BMP is a crucial activation step. Beclomethasone 17-propionate suppresses TNFα, IL-6, and CXCL8 induced by LPS. Beclomethasone 17-propionate's EC50 values for TNFα, CXCL8, and IL-6 are 0.05 nM, 0.01 nM, and 0.1 nM, in that order. The GR-dependent genes FKBP51 and GILZ are upregulated in response to beclomethasone 17-propionate [3].
In vitro, beclomethasone 17-propionate effectively suppresses cytokine production in chronic obstructive pulmonary disease (COPD) lung macrophages. It inhibits LPS-stimulated CXCL8, TNFalpha, and IL-6 production. The EC₅0 values for IL-6, TNFalpha, and CXCL8 are 0.05 nM, 0.01 nM, and 0.1 nM, respectively. It upregulates GR-dependent genes FKBP51 and GILZ in response to treatment. Metabolism of beclomethasone dipropionate to 17-BMP is a crucial activation step for glucocorticoid activity. |
| ln Vivo |
In vivo, beclomethasone 17-propionate is the active metabolite responsible for the therapeutic effects of beclomethasone dipropionate in asthma, allergic rhinitis, and COPD. It exerts potent anti-inflammatory effects by suppressing pro-inflammatory cytokine production. The compound has been studied in preclinical and clinical settings and is approved for human use as part of BDP formulations. In animal models, it reduces airway inflammation and hyperresponsiveness when administered via inhalation. Formulation studies show it is soluble in DMSO (≥125 mg/mL, ~268.83 mM) and can be formulated in vivo in 10% DMSO + 90% Corn Oil (≥2.5 mg/mL, 5.38 mM).
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| Enzyme Assay |
For glucocorticoid receptor binding assays, use cytosol preparations from cells expressing human GR (e.g., A549 lung epithelial cells). Incubate cytosol with 5-10 nM [3H]-dexamethasone in the presence of varying concentrations of beclomethasone 17-propionate (0.01 pM to 100 nM) in binding buffer (10 mM Tris-HCl pH 7.4, 1.5 mM EDTA, 10% glycerol, 5 mM DTT) for 2 h at 4degC. Terminate by adding dextran-coated charcoal, centrifuge, and count supernatant for bound radioactivity. Calculate IC₅0 and Ki. For transactivation assays, use cells transfected with GR-responsive luciferase reporter plasmid (e.g., GRE-Luc). Treat with beclomethasone 17-propionate (0.001-100 nM) for 24 h and measure luciferase activity.
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| Cell Assay |
Culture human lung macrophages isolated from COPD patients or cell lines such as A549 (lung epithelial), THP-1 (monocyte-derived macrophages), or U937 in RPMI 1640 or DMEM with 10% FBS at 37degC with 5% CO2. For cytokine suppression assays, pre-incubate cells with beclomethasone 17-propionate (0.001-10 nM) for 1-2 h, then stimulate with LPS (1-10 ug/mL) for 6-24 h. Collect supernatants and measure IL-6, TNFalpha, CXCL8 using ELISA or Luminex multiplex assays. For GR-dependent gene expression, treat cells with 17-BMP (0.1-10 nM) for 6-24 h and measure FKBP51, GILZ, and MKP-1 mRNA by qPCR. Assess cell viability using MTT or trypan blue exclusion at 24-72 h.
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| Animal Protocol |
For in vivo studies, use male BALB/c mice (6-8 weeks, 20-25 g) or Sprague-Dawley rats (200-250 g) in models of airway inflammation. For ovalbumin (OVA)-induced asthma model, sensitize animals with OVA/alum (i.p.) on days 0 and 14, then challenge intranasally with OVA on days 21-23. Administer beclomethasone 17-propionate via intranasal instillation (10-100 ug/mouse) or intravenous tail vein injection (0.1-1 mg/kg) formulated in 10% DMSO + 90% corn oil. For LPS-induced lung inflammation, administer LPS (5 mg/kg) intratracheally 4 h after compound treatment. Collect bronchoalveolar lavage fluid (BALF) at 24 h for cell counts and cytokine measurement (IL-6, TNFalpha). Harvest lung tissue for histology, MPO assay, and qPCR analysis of inflammatory markers. Monitor body weight daily throughout the study.
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| ADME/Pharmacokinetics |
Beclomethasone 17-propionate has a molecular formula C2₅H33ClO₆ and molecular weight 464.98 g/mol. It is soluble in DMSO at ≥125 mg/mL (≥268.83 mM) for in vitro use and can be formulated in vivo in 10% DMSO + 90% corn oil to achieve ≥2.5 mg/mL (5.38 mM). The compound should be stored as a powder at -20degC for up to 3 years or 4degC for 2 years, and in solvent at -80degC for 6 months or -20degC for 1 month, in a sealed, moisture-protected environment (e.g., under nitrogen).
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| Toxicity/Toxicokinetics |
As a glucocorticoid receptor agonist that has been clinically approved, beclomethasone 17-propionate has a well-characterized safety profile at therapeutic doses. Long-term use can be associated with systemic glucocorticoid side effects including adrenal suppression, osteoporosis, growth retardation in children, and increased risk of infections. For research use, standard laboratory precautions should be followed: use personal protective equipment (gloves, lab coat, safety glasses), avoid inhalation and skin contact. The compound is for research use only and not for human use, though the parent drug is clinically approved. Consult the safety data sheet before handling. Dispose of waste in accordance with local regulations for pharmaceutical waste.
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| References |
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| Additional Infomation |
Beclomethasone ester.
See also: Beclomethasone dipropionate (active portion). Beclomethasone 17-propionate is the active metabolite of beclomethasone dipropionate (BDP), a glucocorticoid approved for the treatment of asthma, allergic rhinitis, and COPD. BDP is a prodrug that is hydrolyzed by esterases to 17-BMP, which has 13-fold higher GR affinity. The compound exerts its anti-inflammatory effects by activating GR, leading to suppression of NF-kappaB and AP-1 pathways and reduced expression of pro-inflammatory cytokines (IL-6, TNFalpha, CXCL8). It is administered via inhalation (for asthma/COPD) or intranasal spray (for rhinitis). Clinical formulations include Qvar, Beclovent, and Beconase. Research applications include studying glucocorticoid signaling in inflammation and airway diseases. |
| Molecular Formula |
C₂₅H₃₃CLO₆
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|---|---|
| Molecular Weight |
464.98
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| Exact Mass |
464.197
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| CAS # |
5534-18-9
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| PubChem CID |
62965
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| Appearance |
White to off-white solid powder
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| Density |
1.3g/cm3
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| Boiling Point |
608.9ºC at 760mmHg
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| Melting Point |
124-126ºC
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| Flash Point |
322ºC
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| Index of Refraction |
1.583
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| LogP |
3.125
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
32
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| Complexity |
925
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| Defined Atom Stereocenter Count |
8
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| SMILES |
CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)Cl)O)C)C)C(=O)CO
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| InChi Key |
OHYGPBKGZGRQKT-XGQKBEPLSA-N
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| InChi Code |
InChI=1S/C25H33ClO6/c1-5-21(31)32-25(20(30)13-27)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,26)19(29)12-23(18,25)4/h8-9,11,14,17-19,27,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
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| Chemical Name |
[(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
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| Synonyms |
Beclomethasone 17propionate; Beclomethasone 17 propionate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~268.83 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.38 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1506 mL | 10.7532 mL | 21.5063 mL | |
| 5 mM | 0.4301 mL | 2.1506 mL | 4.3013 mL | |
| 10 mM | 0.2151 mL | 1.0753 mL | 2.1506 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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