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Fluticasone Furoate

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28 API Suppliers, 12 USDMF, 4 CEP/COS, 2 JDMF, 3 EU WC, 1 KDMF, 18 NDC API, 23 Listed Suppliers, $ API Reference Price

28 API Suppliers
12 USDMF
4 CEP/COS
2 JDMF
3 EU WC
1 KDMF
18 NDC API
23 Listed Suppliers
$ API Reference Price

DEVELOPMENTS

11 Drugs in Development

11 Drugs in Development

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1 Intermediates Suppliers

1 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

108 FDF Dossiers, 9 FDA Orange Book, 80 Europe, 7 Canada, 2 Australia, 7 South Africa, 3 Listed Dossiers

108 FDF Dossiers
9 FDA Orange Book
80 Europe
7 Canada
2 Australia
7 South Africa
3 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

POWDER;INHALATION - 0.05MG/INH;EQ 0.025MG BASE/INH, POWDER;INHALATION - 0.1MG/INH;EQ 0.025MG BASE/INH, POWDER;INHALATION - 0.2MG/INH;EQ 0.025MG BASE/INH, POWDER;INHALATION - 0.05MG/INH, POWDER;INHALATION - 0.1MG/INH, POWDER;INHALATION - 0.2MG/INH, SPRAY, METERED;NASAL - 0.0275MG/SPRAY

drugProductComposition
POWDER;INHALATION - 0.05MG/INH;EQ 0.025MG BASE/INH
POWDER;INHALATION - 0.1MG/INH;EQ 0.025MG BASE/INH
POWDER;INHALATION - 0.2MG/INH;EQ 0.025MG BASE/INH
POWDER;INHALATION - 0.05MG/INH
POWDER;INHALATION - 0.1MG/INH
POWDER;INHALATION - 0.2MG/INH
SPRAY, METERED;NASAL - 0.0275MG/SPRAY

RELATED EXCIPIENT COMPANIES

1 Rochem International Inc, 1 SPI Pharma, 1 DKSH, 1 Jai Radhe Sales, 2 Faran Shimi Pharmaceutical, 8 Gangwal Healthcare, 2 Nanjing Well Pharmaceutical, 4 Actylis, 2 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 1 BASF, 4 DFE Pharma, 1 Finar, 6 Gangwal Chemicals, 1 Ideal Cures Pvt Ltd, 17 Kerry, 1 Kima Chemical, 12 Microlex e.U, 1 Nanjing Bold Chemical, 1 Pharmatrans-Sanaq, 2 Pluviaendo, 2 Prachin Chemical, 7 Roquette, 6 Seppic, 2 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 9 Sigachi Industries, 1 The Dow Chemical Company, 2 Vasa Pharmachem

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DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow, 53 NEWS #PharmaBuzz

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2 DATA COMPILATION #PharmaFlow
53 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions, 73 Finished Drug Prices, 35 Annual Reports

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2 US Medicaid Prescriptions
73 Finished Drug Prices
35 Annual Reports

MARKET PLACE

5 APIs

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5 APIs

PATENTS & EXCLUSIVITIES

111 US Patents, 5 US Exclusivities, 5 Health Canada Patents

patents
111 US Patents
5 US Exclusivities
5 Health Canada Patents

EUROAPI Fluticasone

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

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API REF. PRICE (USD/KG)

$ 41,305

MARKET PLACE

API

FDF

1INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

108

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

11DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

111

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

1,516,640,091

Annual Reports (USD Million)

23,321

Finished Drug Prices

98 RELATED EXCIPIENT COMPANIES

165EXCIPIENTS BY APPLICATIONS

Chemistry

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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

Fluticasone Furoate

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 Formula	C₂₇H₂₉F₃O₆S
Molecular Weight	538.6 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	6
Exact Mass	538.16369430 g/mol
Monoisotopic Mass	538.16369430 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	1080
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Veramyst
PubMed Health	Fluticasone
Drug Classes	Anti-Inflammatory, Corticosteroid, Intermediate, Corticosteroid, Strong
Drug Label	Fluticasone 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 Ingredient	Fluticasone furoate
Dosage Form	Spray, metered
Route	Nasal
Strength	0.0275mg/inh
Market Status	Prescription
Company	Glaxosmithkline

2 of 2
Drug Name	Veramyst
PubMed Health	Fluticasone
Drug Classes	Anti-Inflammatory, Corticosteroid, Intermediate, Corticosteroid, Strong
Drug Label	Fluticasone 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 Ingredient	Fluticasone furoate
Dosage Form	Spray, metered
Route	Nasal
Strength	0.0275mg/inh
Market Status	Prescription
Company	Glaxosmithkline

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

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.

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API Reference Price

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