A glucocorticoid receptor agonist and an active metabolite of beclomethasone dipropionate
Related Products
Active Metabolite(s)
33196Beclomethasone
Pro-drug Form(s)
38880Beclomethasone Dipropionate
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Beclomethasone 17-Propionate

Item No. 38884

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(11β,16β)-9-chloro-11,21-dihydroxy-16-methyl-17-(1-oxopropoxy)-pregna-1,4-diene-3,20-dione
CAS Number
5534-18-9
Synonyms
  • Beclometasone 17-Propionate
  • Beclomethasone 17-Monopropionate
  • 17-BMP
Molecular Formula
C25H33ClO6
Formula Weight
465.0
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
C[C@@]12[C@@](OC(CC)=O)(C(CO)=O)[C@@H](C)C[C@@]1([H])[C@@]3([H])[C@]([C@H](C2)O)([C@@]4(C(CC3)=CC(C=C4)=O)C)Cl
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
InChi Key
OHYGPBKGZGRQKT-XGQKBEPLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Beclomethasone 17-propionate is a glucocorticoid receptor agonist and an active metabolite of the glucocorticoid prodrug beclomethasone dipropionate (Item No. 38880).1,2 It is formed from beclomethasone dipropionate via esterases and is subsequently hydrolyzed to beclomethasone (Item No. 33196).2 Beclomethasone 17-propionate binds to the glucocorticoid receptor (IC50 = 3 nM) and inhibits glucocorticoid receptor transrepression induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014), as well as induces transactivation of the glucocorticoid receptor, in CV-1 cells expressing the human receptor in a concentration-dependent manner.1 It inhibits LPS-induced increases in IL-6, IL-8, and TNF-α levels in primary human lung macrophages from patients with chronic obstructive pulmonary disease (COPD; IC50s = 0.36, 2.04, and 0.21 nM, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tanigawa, K., Nagase, H., Ohmori, K., et al. Species-specific differences in the glucocorticoid receptor transactivation function upon binding with betamethasone-esters. Int. Immunopharmacol. 2(7), 941-950 (2002).

    2. Roberts, J.K., Moore, C.D., Ward, R.M., et al. Metabolism of beclomethasone dipropionate by cytochrome P450 3A enzymes. J. Pharmacol. Exp. Ther. 345(2), 308-316 (2013).

    3. Plumb, J., Robinson, L., Lea, S., et al. Evaluation of glucocorticoid receptor function in COPD lung macrophages using beclomethasone-17-monopropionate. PLoS One 8(5), e64257 (2013).