Fluticasone furoate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Fluticasone furoate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Fluticasone furoate?

The molecule Fluticasone furoate presents a molecular formula of C27H29F3O6S and its IUPAC name is [(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.

Fluticasone furoate (SCH-98110) is a synthetic trifluorinated corticosteroid with anti-inflammatory and immunomodulatory activities. It is a prodrug of the active metabolite fluticasone, which is a potent agonist of the glucocorticoid receptor (GR). Fluticasone furoate binds to and activates the GR, which leads to the transcription of anti-inflammatory genes. In addition, fluticasone furoate inhibits the release of pro-inflammatory cytokines and mediators from immune cells. This results in the suppression of the inflammatory response..

Fluticasone furoate is used for the treatment of allergic rhinitis and asthma. It is also used for the treatment of eosinophilic esophagitis..

Fluticasone furoate is well tolerated and has a good safety profile. The most common side effects are nasopharyngitis, headache, and upper respiratory tract infection..

Fluticasone furoate is a potent, long-acting, and selective agonist of the GR. It is an effective anti-inflammatory and immunomodulatory agent. Fluticasone furoate is well tolerated and has a good safety profile..

3D structure

Cartesian coordinates

Geometry of Fluticasone furoate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Fluticasone furoate XTULMSXFIHGYFS-VLSRWLAYSA-N chemical compound 2D structure molecule svg
Fluticasone furoate

 

Molecule descriptors

 
IUPAC name[(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
InChI codeInChI=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
SMILESC[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(OC(=O)c1ccco1)C(=O)SCF

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-17-(((FLUORO-METHYL)THIO)CARBONYL)-11-HYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIEN-17-YL 2-FURANCARBOXYLATE
  • (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-17-(((FLUOROMETHYL)THIO)CARBONYL)-11-HYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIEN-17-YL 2-FUROATE
  • (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-17-(((FLUOROMETHYL)THIO)CARBONYL)-11-HYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIEN-17-YL-2-FURANCARBOXYLATE
  • (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(((fluoromethyl)thio)carbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl furan-2-carboxylate
  • (6alpha,11alpha,14beta,16alpha,17alpha)-6,9-Difluoro-17-{[(Fluoromethyl)sulfanyl]carbonyl}-11-Hydroxy-16-Methyl-3-Oxoandrosta-1,4-Dien-17-Yl Furan-2-Carboxylate
  • (6alpha,11alpha,14beta,16alpha,17alpha)-6,9-difluoro-17-{[(fluoromethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoan
  • (6alpha,11alpha,14beta,16alpha,17alpha)-6,9-difluoro-17-{[(fluoromethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoan drosta-1,4-dien-17-yl furan-2-carboxylate
  • (6alpha,11beta,16alpha,17alpha)-6,9-Difluoro-17-(((fluoromethyl)thio)carbonyl)-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-yl-2-furancarboxylate
  • 397864-44-7
  • 6.ALPHA.,9-DIFLUORO-17-(((FLUOROMETHYL)SULFANYL)CARBONYL)-11.BETA.-HYDROXY-16.ALPHA.-METHYL-3-OXOANDROSTA-1,4-DIEN-17.ALPHA.-YL FURAN-2-CARBOXYLATE
  • 6alpha,9-Difluoro-17-(((fluoromethyl)sulfanyl)carbonyl)-11beta-hydroxy-16alpha-methyl-3-oxoandrosta-1,4-dien-17alpha-yl furan-2-carboxylate
  • 6alpha,9-difluoro-17beta-{[(fluoromethyl)sulfanyl]carbonyl}-11beta-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17alpha-yl 2-furoate
  • 911210-90-7
  • ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID, 6,9-DIFLUORO-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYL-3-OXO-, S-(FLUOROMETHYL) ESTER, (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-
  • ARNUITY ELLIPTA COMPONENT FLUTICASONE FUROATE
  • Alisade
  • Allermist
  • Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-17-((2- furanylcarbonyl)oxy)-11-hydroxy-16-methyl-3-oxo-, S-(fluoromethyl) ester, (6alpha,11beta,16alpha,17alpha)-
  • Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-17-((2- furanylcarbonyl)oxy)-11-hydroxy-16-methyl-3-oxo-, S-(fluoromethyl) ester, (6alpha,11beta,16alpha,17alpha)-
  • Arnuity Ellipta
  • Avamys
  • Avamys pound>> Veramyst pound>> Allermist
  • BCP18136
  • BDBM50354851
  • BREO ELLIPTA COMPONENT FLUTICASONE FUROATE
  • CS-0003822
  • D06315
  • DB08906
  • E86983
  • Ennhale
  • FLUTICASONE FUROATE COMPONENT OF ARNUITY ELLIPTA
  • FLUTICASONE FUROATE COMPONENT OF BREO ELLIPTA
  • FLUTICASONE FUROATE COMPONENT OF TRELEGY ELLIPTA
  • Flonase Sensimist
  • Flonase Sensimist Allergy Relief
  • Fluticasone furancarboxylate
  • Fluticasone furoate
  • Fluticasone furoate (JAN/USAN/INN)
  • Furamist
  • GSK 685 698
  • GSK 685698
  • GSK-685968
  • GSK685968
  • GTPL10892
  • GW 685698X
  • GW-685698
  • GW-685698X
  • GW6
  • GW685698X
  • HY-15234
  • JS86977WNV
  • Q2166700
  • TRELEGY ELLIPTA COMPONENT FLUTICASONE FUROATE
  • Veramyst
  • [(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
  • drosta-1,4-dien-17-yl furan-2-carboxylate
  • fluticasonum furoas
  • furoate de fluticasone
  • furoato de fluticasona
  • gw685698
  • s6487

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3992105
  • UNII-JS86977WNV
  • DTXSID401024827
  • CHEMBL1676
  • CHEBI:74899
  • SCHEMBL140504

Physico-Chemical properties

IUPAC name[(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
Molecular formulaC27H29F3O6S
Molecular weight538.576
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity130.39
LogP4.9
Topological polar surface area119.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.