GW6

(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

Created:2008-03-21
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count66
Chiral Atom Count9
Bond Count70
Aromatic Bond Count5
2D diagram of GW6
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Chemical Component Summary

Name(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
SynonymsFluticasone furoate
Systematic Name (OpenEye OEToolkits)[(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
FormulaC27 H29 F3 O6 S
Molecular Weight538.576
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(SCF)C5(OC(=O)c1occc1)C4(C)CC(O)C3(F)C2(C=CC(=O)C=C2C(F)CC3C4CC5C)C
SMILESCACTVS3.341C[CH]1C[CH]2[CH]3C[CH](F)C4=CC(=O)C=C[C]4(C)[C]3(F)[CH](O)C[C]2(C)[C]1(OC(=O)c5occc5)C(=O)SCF
SMILESOpenEye OEToolkits1.5.0CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)SCF)OC(=O)c5ccco5)C)O)F)C)F
Canonical SMILESCACTVS3.341 C[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)c5occc5)C(=O)SCF
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)SCF)OC(=O)c5ccco5)C)O)F)C)F
InChIInChI1.03 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
InChIKeyInChI1.03 XTULMSXFIHGYFS-VLSRWLAYSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB08906 
NameFluticasone furoate
Groups approved
DescriptionFluticasone furoate is a synthetic glucocorticoid available as an inhaler and nasal spray for various inflammatory indications[FDA Label][F4364]. Fluticasone furoate was first approved in 2007[L5965].
Synonyms
  • Furoate de fluticasone
  • Fluticasonum furoas
  • Fluticasone furoate
  • Furoato de fluticasona
Brand Names
  • Relvar Ellipta
  • Fluticasone Furoate and Vilanterol
  • Flonase Sensimist Allergy Relief
  • Veramyst
  • Trelegy Ellipta
IndicationFluticasone furoate is indicated for once-daily maintenance (i.e. prophylactic) treatment of asthma in patients ≥5 years old.[L40838] Fluticasone furoate is available in two combination medications - one in combination with [vilanterol] and one in combination with both vilanterol and [umeclidinium]- which are both indicated for the management of chronic obstructive pulmonary disease (COPD) and for the treatment of asthma in patients ≥18 years old for the vilanterol-umeclidinium-fluticasone product and ≥5 years old for the vilanterol-fluticasone product.[L44456,L46481] Fluticasone furoate is available over the counter as a nasal spray for the symptomatic treatment of hay fever and other upper respiratory allergies in patients ≥2 years old.[L40843]
Categories
  • Adrenal Cortex Hormones
  • Agents to Treat Airway Disease
  • Androstanes
  • Androstenes
  • Corticosteroids
ATC-Code
  • R03AL08
  • R01AD12
  • R03AK10
  • R03BA09
CAS number397864-44-7

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Glucocorticoid receptorMDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...unknownagonist
Progesterone receptorMTELKAKGPRAPHVAGGPPSPEVGSPLLCRPAAGPFPGSQTSDTLPEVSA...unknownagonist
Mineralocorticoid receptorMETKGYHSLPEGLDMERRWGQVSQAVERSSLGPTERTDENNYMEIVNVSC...unknownantagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor,inducer
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate,inhibitor,inducer
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1676
PubChem 9854489
ChEMBL CHEMBL1676
ChEBI CHEBI:74899