(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-({[fluoro(2H2)methyl]sulfanyl}carbonyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl (2H3)furan-2-carboxylate

• ChemBase ID: 169303
• Molecular Formular: C27H29F3O6S
• Molecular Mass: 538.5757696
• Monoisotopic Mass: 538.16369431
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@]2(OC(=O)c1ccco1)C(=O)SCF)C)C)O)F)F)C
• 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
• 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
• InChIKey: XTULMSXFIHGYFS-VLSRWLAYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-({[fluoro(^2H₂)methyl]sulfanyl}carbonyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl (^2H₃)furan-2-carboxylate
• IUPAC Traditional name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-({[fluoro(^2H₂)methyl]sulfanyl}carbonyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl (^2H₃)furan-2-carboxylate
• Synonyms: (6α,11β,16α,17α)-6,9-Difluoro-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carbothioic Acid S-(Fluoromethyl) Ester-d5; Allermist-d5; Avamys-d5; GSK 685 698-d5; GW 685698X-d5; Fluticasone-d5 Furoate

Database IDs

• PubChem SID: 162263435
• PubChem CID: 71316901

CALCULATED PROPERTIES

• Acid pKa: 13.557201
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.13189
• LogD (pH = 7.4): 4.1318893
• Log P: 4.13189
• Molar Refractivity: 130.0848 cm^3
• Polarizability: 50.13635 Å^3
• Polar Surface Area: 93.81 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F599512

Labelled Fluticasone Furoate (F599510). A synthetic corticosteroid derived from fluticasone for treatment of seasonal allergic rhinitis.

REFERENCES

• DeWester, J., et al.: Allergy Asthma Proc., 24, 331 (2003)
• Hughes, S., et al.: Drug Metab. Dispos., 36, 2337 (2003)
• Meltzer, E., et al.: Clin. Drug Investig., 29, 79 (2003)