beclometasone   

GtoPdb Ligand ID: 7059

Synonyms: beclomethasone | SCH-18020W
beclometasone is an approved drug
Compound class: Synthetic organic
Comment: Beclometasone is the active form of the prodrug beclometasone dipropionate.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 94.83
Molecular weight 408.17
XLogP 1.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCC(=O)C1(O)C(C)CC2C1(C)CC(O)C1(C2CCC2=CC(=O)C=CC12C)Cl
Isomeric SMILES OCC(=O)[C@@]1(O)[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
InChI InChI=1S/C22H29ClO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
InChI Key NBMKJKDGKREAPL-DVTGEIKXSA-N
No information available.
Summary of Clinical Use
Used for the prophylaxis of asthma. However, there is no information regarding approval for use of this drug on the US FDA or European Medicines Agency websites, although the compound does have an INN. Other national approval agencies may have granted marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects
Beclometasone is a glucocorticoid receptor (GR) agonist. 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 humoral immune responses. Beclometasone dipropionate, once converted to its active drug beclometasone, therefore induces an antiinflammatory response.