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    Fluticasone Furoate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Veramyst, Avamys, 397864-44-7, Allermist, Furamist, Arnuity ellipta
    Molecular Formula
    C27H29F3O6S
    Molecular Weight
    538.6  g/mol
    InChI Key
    XTULMSXFIHGYFS-VLSRWLAYSA-N
    FDA UNII
    JS86977WNV
    Fluticasone Furoate is the furoate salt form of fluticasone, a synthetic trifluorinated glucocorticoid receptor agonist with anti-allergic, anti-inflammatory and anti-pruritic effects. Upon administration, fluticasone binds to and activates glucocorticoid receptor, resulting in the activation of lipocortin. Lipocortin, in turn, inhibits cytosolic phospholipase A2 and the cascade of reactions involved in the synthesis of inflammatory mediators, such as prostaglandins and leukotrienes. Secondly, mitogen-activated protein kinase (MAPK) phosphatase 1 is induced, which leads to dephosphorylation and inactivation of Jun N-terminal kinase and directly inhibits c-Jun mediated transcription. Finally, transcriptional activity of nuclear factor (NF)-kappa-B is blocked, thereby inhibiting the transcription of cyclooxygenase 2 (COX-2), which is essential for prostaglandin production.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 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
    2.1.2 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
    2.1.3 InChI Key
    XTULMSXFIHGYFS-VLSRWLAYSA-N
    2.1.4 Canonical SMILES
    CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)SCF)OC(=O)C5=CC=CO5)C)O)F)C)F
    2.1.5 Isomeric SMILES
    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)C5=CC=CO5)C)O)F)C)F
    2.2 Other Identifiers
    2.2.1 UNII
    JS86977WNV
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Veramyst

    2. Avamys

    3. 397864-44-7

    4. Allermist

    5. Furamist

    6. Arnuity Ellipta

    7. Ennhale

    8. Gsk 685 698

    9. Flonase Sensimist

    10. Gw685698x

    11. Gsk 685698

    12. Gw-685698x

    13. Js86977wnv

    14. Chebi:74899

    15. Gsk685968

    16. Gsk-685968

    17. Gw 685698x

    18. [(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

    19. Alisade

    20. (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

    21. Unii-js86977wnv

    22. Fluticasone Furoate [usan:inn]

    23. Fluticasonum Furoas

    24. Veramyst (tn)

    25. Furoate De Fluticasone

    26. Furoato De Fluticasona

    27. Fluticasone Furancarboxylate

    28. Chembl1676

    29. Schembl140504

    30. Flonase Sensimist Allergy Relief

    31. Fluticasone Furoate [mi]

    32. Gtpl10892

    33. Fluticasone Furoate [inn]

    34. Fluticasone Furoate [jan]

    35. Gw685698

    36. Dtxsid401024827

    37. Fluticasone Furoate [usan]

    38. Fluticasone Furoate [vandf]

    39. Bcp18136

    40. Fluticasone Furoate [mart.]

    41. Zinc3992105

    42. Bdbm50354851

    43. Fluticasone Furoate [who-dd]

    44. S6487

    45. Fluticasone Furoate (jan/usan/inn)

    46. Fluticasone Furoate [ema Epar]

    47. Db08906

    48. Fluticasone Furoate [orange Book]

    49. Hy-15234

    50. Avamys Pound>> Veramyst Pound>> Allermist

    51. Gw-685698

    52. Cs-0003822

    53. Drosta-1,4-dien-17-yl Furan-2-carboxylate

    54. D06315

    55. E86983

    56. Breo Ellipta Component Fluticasone Furoate

    57. Arnuity Ellipta Component Fluticasone Furoate

    58. Fluticasone Furoate Component Of Breo Ellipta

    59. Q2166700

    60. Trelegy Ellipta Component Fluticasone Furoate

    61. Fluticasone Furoate Component Of Arnuity Ellipta

    62. Fluticasone Furoate Component Of Trelegy Ellipta

    63. (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

    64. (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

    65. (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

    66. (6alpha,11alpha,14beta,16alpha,17alpha)-6,9-difluoro-17-{[(fluoromethyl)sulfanyl]carbonyl}-11-hydroxy-16-methyl-3-oxoan

    67. (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

    68. (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

    69. (6alpha,11beta,16alpha,17alpha)-6,9-difluoro-17-(((fluoromethyl)thio)carbonyl)-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-yl-2-furancarboxylate

    70. 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

    71. 6alpha,9-difluoro-17-(((fluoromethyl)sulfanyl)carbonyl)-11beta-hydroxy-16alpha-methyl-3-oxoandrosta-1,4-dien-17alpha-yl Furan-2-carboxylate

    72. 6alpha,9-difluoro-17beta-{[(fluoromethyl)sulfanyl]carbonyl}-11beta-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17alpha-yl 2-furoate

    73. 911210-90-7

    74. 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)-

    75. 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)-

    76. 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.)-

    77. Gw6

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 538.6 g/mol
    Molecular Formula C27H29F3O6S
    XLogP34.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count6
    Exact Mass538.16369430 g/mol
    Monoisotopic Mass538.16369430 g/mol
    Topological Polar Surface Area119 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity1080
    Isotope Atom Count0
    Defined Atom Stereocenter Count9
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameVeramyst
    PubMed HealthFluticasone
    Drug ClassesAnti-Inflammatory, Corticosteroid, Intermediate, Corticosteroid, Strong
    Drug LabelFluticasone furoate, the active component of VERAMYST Nasal Spray, is a synthetic fluorinated corticosteroid having the chemical name (6,11,16,17)-6,9-difluoro-17-{[(fluoro-methyl)thio]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-...
    Active IngredientFluticasone furoate
    Dosage FormSpray, metered
    RouteNasal
    Strength0.0275mg/inh
    Market StatusPrescription
    CompanyGlaxosmithkline

    2 of 2  
    Drug NameVeramyst
    PubMed HealthFluticasone
    Drug ClassesAnti-Inflammatory, Corticosteroid, Intermediate, Corticosteroid, Strong
    Drug LabelFluticasone furoate, the active component of VERAMYST Nasal Spray, is a synthetic fluorinated corticosteroid having the chemical name (6,11,16,17)-6,9-difluoro-17-{[(fluoro-methyl)thio]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-...
    Active IngredientFluticasone furoate
    Dosage FormSpray, metered
    RouteNasal
    Strength0.0275mg/inh
    Market StatusPrescription
    CompanyGlaxosmithkline

    4.2 Drug Indication

    Fluticasone furoate is indicated as an inhaler for the treatment and management of asthma by prophylaxis. The fluticasone furoate nasal spray is indicated for treating season and perennial allergic rhinitis.

    FDA Label

    Adults, adolescents (12 years and over) and children (6-11 years). Avamys is indicated for the treatment of the symptoms of allergic rhinitis.

    Adults, adolescents (12 years and over) and children (6 - 11 years). Alisade is indicated for the treatment of the symptoms of allergic rhinitis.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Systemically, in vitro experiments show fluticasone furoate activates glucocorticoid receptors, inhibits nuclear factor kappa b, and inhibits lung eosinophilia in rats.

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.3 ATC Code

    R01AD12

    R01AD12

    R - Respiratory system

    R01 - Nasal preparations

    R01A - Decongestants and other nasal preparations for topical use

    R01AD - Corticosteroids

    R01AD12 - Fluticasone furoate

    R - Respiratory system

    R03 - Drugs for obstructive airway diseases

    R03B - Other drugs for obstructive airway diseases, inhalants

    R03BA - Glucocorticoids

    R03BA09 - Fluticasone furoate

    5.4 Absorption, Distribution and Excretion

    Absorption

    Intranasal exposure of fluticasone furoate results in patients swallowing a larger portion of the dose. However, absorption is poor and metabolism is high, therefore there is negligible systemic exposure with a nasal bioavailability of 0.50% and oral bioavialability of 1.26%. Inhaled bioavailability is 13.9%. A study of 24 healthy Caucasian males showed an inhaled bioavailability of 6.3-18.4%.

    Route of Elimination

    Fluticasone furoate is eliminated 90% in the feces and 1-2% in the urine.

    Volume of Distribution

    608L at steady state for intravenous administration of fluticasone furoate. Other reports suggest the mean volume of distribution at steady state is 661L. A study of 24 healthy Caucasian males showed a volume of distribution at steady state of 704L following intravenous administration.

    Clearance

    57.8L/h for fluticasone furoate. A study of 24 healthy Caucasian males showed a clearance of 71.8L/h following intravenous administration.

    5.5 Metabolism/Metabolites

    Fluticasone furoate is cleared from hepatic metabolism by cytochrome P450 3A4. Fluticasone furoate is hydrolysed at the FIVE-S-fluoromethyl carbothioate group, forming an inactive metabolite.

    5.6 Biological Half-Life

    15.1 hours for intranasal fluticasone furoate and 24 hours for the inhaled formulation. A study of 24 healthy Caucasian males showed a half life of 13.6 hours following intravenous administration and 17.3-23.9 hours followed inhalation.

    5.7 Mechanism of Action

    Fluticasone furoate works through an unknown mechanism to affect the action of various cell types and mediators of inflammation. In vitro experiments show fluticasone furoate activating glucocorticoid receptors, inhibiting nuclear factor kappa b, and inhibiting lung eosinophilia in rats.