beclometasone dipropionate   Click here for help

GtoPdb Ligand ID: 5894

Synonyms: beclomethasone dipropionate | Beconase® | Qnasl® | Vancenase®
Approved drug Immunopharmacology Ligand
beclometasone dipropionate is an approved drug (EMA (2017))
Compound class: Synthetic organic
Comment: A synthetic glucocorticoid.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 106.97
Molecular weight 520.22
XLogP 2.83
No. Lipinski's rules broken 0
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Canonical SMILES CCC(=O)OC1(C(C)CC2C1(C)CC(O)C1(C2CCC2=CC(=O)C=CC12C)Cl)C(=O)COC(=O)CC
Isomeric SMILES CCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)Cl)C(=O)COC(=O)CC
InChI InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
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Summary of Clinical Use Click here for help
EMA approval covers beclometasone dipropionate in fixed dose combinations with formoterol and glycopyrrolate that can be used to manage chronic obstructive pulmonary disease (COPD). It may also be used as a monotherapy to control the symptoms of asthma and allergic rhinitis in other jurisdictions.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Agonist of the glucocorticoid receptor (GR). By binding to this receptor, inhibition of leukocyte filtration at the site of inflammation occurs, along with interference of the function of inflammatory mediators and suppression of the humoral immune responses. Beclometasone dipropionate, once converted to its active form beclometasone, induces an antiinflammatory response.