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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View more information in the IUPHAR Pharmacology Education Project: fluticasone

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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
InChI Key MGNNYOODZCAHBA-GQKYHHCASA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
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.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)