fluocinolone acetonide   

GtoPdb Ligand ID: 7077

Synonyms: Capex® | Iluvien® | Synalar®
fluocinolone acetonide is an approved drug (FDA (1963))
Compound class: Synthetic organic
Comment: Fluocinolone acetonide is a corticosteroid.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 93.06
Molecular weight 452.2
XLogP 1.15
No. Lipinski's rules broken 0
Canonical SMILES OCC(=O)C12OC(OC1CC1C2(C)CC(O)C2(C1CC(C1=CC(=O)C=CC21C)F)F)(C)C
Isomeric SMILES OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1C[C@@H](C1=CC(=O)C=C[C@]21C)F)F)(C)C
InChI InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
No information available.
Summary of Clinical Use
Fluocinolone acetonide is the active component in creams used to treat inflammatory and pruritic skin conditions. An intravitreal implant containing fluocinolone acetonide was approved (by the US FDA) for the management of diabetic macular edema in 2014. The Yutiq® intravitreal implant containing fluocinolone acetonide was FDA approved for the treatment of non-infectious posterior uveitis in October 2018.
Mechanism Of Action and Pharmacodynamic Effects
As an agonist of the glucocorticoid receptor, fluocinolone acetonide 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.