fluticason furoate (CED0005220)

Record Information
Version1.0
Creation Date2016-06-03 11:54:18 UTC
Update Date2026-08-22 07:25:40 UTC
Accession NumberCHEM044234
Identification
Common Namefluticason furoate
ClassSmall Molecule
Description
fluticason furoate belongs to the steroid esters, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 538.58 g/mol, fluticason furoate is a heavy molecule. Its chemical formula is C27H29F3O6S. This compound is classified within the superclass of lipids and lipid-like molecules. The substance is found in or released from two recorded sources: healthcare, pharmaceuticals & veterinary products, specifically nasal preparations and drugs for obstructive airway diseases. Recorded exposure routes include nasal, respiratory, and intrasinal administration. In terms of biological activity, fluticason furoate interacts with three recorded protein targets, acting as an agonist/antagonist of the glucocorticoid receptor (NR3C1), the progesterone receptor (PGR), and the mineralocorticoid receptor (NR3C2).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Fluticasonum furoasChEBI
Furoate de fluticasoneChEBI
Furoato de fluticasonaChEBI
GSK 685698ChEBI
VeramystChEBI
Furoic acid de fluticasoneGenerator
Fluticasone furoic acidGenerator
Chemical FormulaC27H29F3O6S
Average Molecular Mass538.576 g/mol
Monoisotopic Mass538.164 g/mol
CAS Registry Number397864-44-7
IUPAC Name(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl furan-2-carboxylate
Traditional Nameveramyst
SMILES[H][C@@]12C[C@@H](C)[C@](OC(=O)C3=CC=CO3)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=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 KeyXTULMSXFIHGYFS-VLSRWLAYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • Hydroxysteroid
  • Halo-steroid
  • 6-halo-steroid
  • 9-halo-steroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • Delta-1,4-steroid
  • Furoic acid ester
  • Furoic acid or derivatives
  • Furan
  • Cyclic alcohol
  • Heteroaromatic compound
  • Halohydrin
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Cyclic ketone
  • Carbothioic s-ester
  • Carboxylic acid ester
  • Fluorohydrin
  • Ketone
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Monocarboxylic acid or derivatives
  • Alkyl fluoride
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alkyl halide
  • Organosulfur compound
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.73ALOGPS
logP4.13ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.56ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area93.81 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity130.08 m³·mol⁻¹ChemAxon
Polarizability51.55 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-1001290000-ba6113fa855cedcb900eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-1191110000-9cadbfbad3f7e8d99622Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xr-9083100000-3d2dc4029efbfa4f220cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-9100000000-0b7cf863dc6c16ffd5e7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9200110000-dec4502a34ac6f04b2eaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-9100100000-69ae74d57ed770f18afdNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
248.0Log mg/kg[140:440]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
389Nasal preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
391Drugs for obstructive airway diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
2 pathways
Fluticasone furoate Action Pathway
Fluticasone furoate Action Pathway
Fluticasone furoate Drug Metabolism Action Pathway
Fluticasone furoate Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)2.64687
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)2.02408
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)5.52729
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)17.2825
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.389246
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)4.43741
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)9.34191
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)75.4359
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)22.1092
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)8.17417
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.934191
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)94.509
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)2.02408
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)135.224
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)89.3709
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)775.378
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)6384.18
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)1625.88
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)4996.91
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)5552.05
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)5555.71
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)2753.06
Protein kinase C epsilon type structureClick to view 3D structureProtein kinase C epsilon typeQ02156HumansPredicted (SEA)2568.64
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)5506.82
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)5727.29
Concentrations
Not Available
External Links
DrugBank IDDB08906
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluticasone_furoate
Chemspider IDNot Available
ChEBI ID74899
PubChem Compound ID9854489
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21828231
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22170807
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22342538
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22387656
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22391079
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22614920
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22738148
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23018908
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23116485
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23184737
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23200625
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23332861
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23352226
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23406601
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23440247
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23548539
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23578031
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23676578
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23719680
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23735179
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23806459
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23821392
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23846316