fluticasone   Click here for help

GtoPdb Ligand ID: 6699

Synonyms: Advair® | Avamys® | Flovent HFA® | Veramyst®
Approved drug Immunopharmacology Ligand
fluticasone is an approved drug (FDA (1994), EMA (2008))
Compound class: Synthetic organic
Comment: The DrugBank entry listed here refers to fluticasone propionate with CAS registry number 80474-14-2. ChEMBL lists fluticasone propionate as a glucocorticoid receptor agonist, but not the fluticasone parent molecule.

Breo Ellipta®, approved by the FDA in 2013, is a fixed-dose formulation containing fluticasone furoate and vilanterol.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 99.9
Molecular weight 444.16
XLogP 2.4
No. Lipinski's rules broken 0
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Canonical SMILES FCSC(=O)C1(O)C(C)CC2C1(C)CC(O)C1(C2CC(C2=CC(=O)C=CC12C)F)F
Isomeric SMILES FCSC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F
InChI InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
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Summary of Clinical Use Click here for help
The approved drug can contain fluticasone propionate. This formulation is used to treat various inflammatory conditions including aleviation of inflammatory and pruritic symptoms of dermatoses and psoriasis (applied topically), for controlling symptoms of allergic and non-allergic rhinitis (used intranasally) and to treat asthma (inhalation and oral administration). Fluticasone furoate (in Flonase® SensimistTM Allergy Relief) is approved as an over-the-counter medication providing non-drowsy, 24-hour relief of both nose- and eye-related allergy symptoms.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The antiinflammatory actions of corticosteroids are thought to involve inhibition of several pathways involved in resolution of inflammation, including inhibition of cytosolic phospholipase A2 (through activation of lipocortin-1 (annexin)) which controls the biosynthesis of pro-inflammatory prostaglandins and leukotrienes.
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