flumethasone pivalate   

GtoPdb Ligand ID: 7075

Synonyms: Locorten®
flumethasone pivalate is an approved drug
Compound class: Synthetic organic
Comment: Flumethasone pivalate is a corticosteroid.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 100.9
Molecular weight 494.25
XLogP 2.13
No. Lipinski's rules broken 0
Canonical SMILES O=C1C=CC2(C(=C1)C(F)CC1C2(F)C(O)CC2(C1CC(C2(O)C(=O)COC(=O)C(C)(C)C)C)C)C
Isomeric SMILES O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)COC(=O)C(C)(C)C)C)C)C
InChI InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1
No information available.
Summary of Clinical Use
Used to reduce skin inflammation caused by allergic reactions, eczema and psoriasis. However, there is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects
As an agonist of the glucocorticoid receptor, flumethasone pivalate modulates expression of genes containing the glucocorticoid response element (GRE). Although complex, the response appears to include inhibition of the biosynthesis of pro-inflammatory prostaglandins and leukotrienes. However, we have been unable to find affinity data for this drug to substantiate its MMOA.