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fluticasone furoate   Click here for help

GtoPdb Ligand ID: 10892

Synonyms: Arnuity Ellipta | Avamys | FF | Flonase Sensimist | Veramyst
Approved drug PDB Ligand Immunopharmacology Ligand
fluticasone furoate is an approved drug (FDA (2007))
Compound class: Synthetic organic
Comment: A synthetic glucocorticoid (glucocorticoid receptor agonist) available as an inhaler and nasal spray for various inflammatory indications.

fluticasone furoate is commercially available from our sponsors

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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Click here for structure editor
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 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 119.11
Molecular weight 538.16
XLogP 3.55
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)[C@@]1(OC(=O)c2ccco2)[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
Isomeric SMILES FCSC(=O)[C@@]1(OC(=O)c2ccco2)[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/C27H29F3O6S/c1-14-9-16-17-11-19(29)18-10-15(31)6-7-24(18,2)26(17,30)21(32)12-25(16,3)27(14,23(34)37-13-28)36-22(33)20-5-4-8-35-20/h4-8,10,14,16-17,19,21,32H,9,11-13H2,1-3H3/t14-,16+,17+,19+,21+,24+,25+,26+,27+/m1/s1
InChI Key XTULMSXFIHGYFS-VLSRWLAYSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (2007)
IUPAC Name Click here for help
[(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate
International Nonproprietary Names Click here for help
INN number INN
8521 fluticasone furoate
Synonyms Click here for help
Arnuity Ellipta | Avamys | FF | Flonase Sensimist | Veramyst
Database Links Click here for help
CAS Registry No. 397864-44-7
ChEMBL Ligand CHEMBL1676
DrugBank Ligand DB08906
DrugCentral Ligand 4554, 4554
GtoPdb PubChem SID 405560333
PubChem CID 9854489
RCSB PDB Ligand GW6
Search Google for chemical match using the InChIKey XTULMSXFIHGYFS-VLSRWLAYSA-N
Search Google for chemicals with the same backbone XTULMSXFIHGYFS
Search PubMed clinical trials fluticasone furoate
Search PubMed titles fluticasone furoate
Search PubMed titles/abstracts fluticasone furoate
UniChem Compound Search for chemical match using the InChIKey XTULMSXFIHGYFS-VLSRWLAYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XTULMSXFIHGYFS-VLSRWLAYSA-N

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MedChemExpress
Fluticasone furoate (links to external site)
Cat. No. HY-15234