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Beclomethasone 17-Propionate

Names

[ CAS No. ]:
5534-18-9

[ Name ]:
Beclomethasone 17-Propionate

[Synonym ]:
[(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

Biological Activity

[Description]:

Beclomethasone 17-propionate (Beclomethasone-17-monopropionate), an active metabolite of Beclomethasone dipropionate (HY-13571), is a glucocorticoid receptor (GR) agonist. Beclomethasone 17-propionate exhibits greater affinity for GR than Beclomethasone dipropionate. Beclomethasone 17-propionate effectively suppresses cytokine production in chronic obstructive pulmonary disease (COPD) lung macrophages[1][2][3].

[Related Catalog]:

Research Areas >> Inflammation/Immunology
Signaling Pathways >> GPCR/G Protein >> Glucocorticoid Receptor

[In Vitro]

Metabolism of Beclomethasone dipropionate to 17-BMP is an important activation step. Beclomethasone 17-propionate inhibits LPS-stimulated CXCL8, TNFα and IL-6. The EC50 values of Beclomethasone 17-propionate for IL-6, TNFα and CXCL8 were 0.05 nM, 0.01 nM and 0.1 nM, respectively. Beclomethasone 17-propionate evokes upregulation of the GR dependent genes FKBP51 and GILZ[3].

[References]

[1]. Würthwein G, et al. Activation of beclomethasone dipropionate by hydrolysis to beclomethasone-17-monopropionate. Biopharm Drug Dispos. 1990 Jul;11(5):381-94.

[2]. Roberts JK, et al. Metabolism of beclomethasone dipropionate by cytochrome P450 3A enzymes. J Pharmacol Exp Ther. 2013 May;345(2):308-16.

[3]. Plumb J, et al. Evaluation of glucocorticoid receptor function in COPD lung macrophages using beclomethasone-17-monopropionate. PLoS One. 2013 May 21;8(5):e64257.

Chemical & Physical Properties

[ Density]:
1.3g/cm3

[ Boiling Point ]:
608.9ºC at 760mmHg

[ Melting Point ]:
124-126ºC

[ Molecular Formula ]:
C25H33ClO6

[ Molecular Weight ]:
464.97900

[ Flash Point ]:
322ºC

[ Exact Mass ]:
464.19700

[ PSA ]:
100.90000

[ LogP ]:
3.12590

[ Index of Refraction ]:
1.583

[ Storage condition ]:
-20°C

Related Compounds