fluticason furoate (CHEM044234)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:54:18 UTC
Update Date2016-11-09 01:23:05 UTC
Accession NumberCHEM044234
Identification
Common Namefluticason furoate
ClassSmall Molecule
DescriptionA trifluorinated corticosteroid that consists of 6alpha,9-difluoro-11beta,17alpha-dihydroxy-17beta-{[(fluoromethyl)sulfanyl]carbonyl}-16-methyl-3-oxoandrosta-1,4-diene bearing a 2-furoyl substituent at position 17. Used in combination with vilanterol trifenate for treatment of bronchospasm associated with chronic obstructive pulmonary disease.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-1001290000-ba6113fa855cedcb900eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-1191110000-9cadbfbad3f7e8d99622Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-9083100000-3d2dc4029efbfa4f220cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9100000000-0b7cf863dc6c16ffd5e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9200110000-dec4502a34ac6f04b2eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9100100000-69ae74d57ed770f18afdSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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