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Flunisolide

Flunisolide

Synopsis, Chemistry

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Also known as: 3385-03-3, Aerobid, Rhinalar, Synaclyn, Flunisolide anhydrous, Nasarel

Molecular Formula

C₂₄H₃₁FO₆

Molecular Weight

434.5 g/mol

InChI Key

XSFJVAJPIHIPKU-XWCQMRHXSA-N

FDA UNII

78M02AA8KF

Flunisolide is a synthetic corticosteroid with antiinflammatory and antiallergic properties. Flunisolide is a glucocorticoid receptor agonist that binds to cytoplasmic glucocorticoid receptors and subsequently translocates to the nucleus where it initiates the transcription of glucocorticoid-responsive genes such as lipocortins. Lipocortins inhibit phospholipase A2, thereby blocking the release of arachidonic acid from membrane phospholipids and preventing the synthesis of prostaglandins and leukotrienes, both are potent mediators of inflammation.

Flunisolide anhydrous is a Corticosteroid. The mechanism of action of flunisolide anhydrous is as a Corticosteroid Hormone Receptor Agonist.

1 2D Structure

Flunisolide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

2.1.2 InChI

InChI=1S/C24H31FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h5-7,13-14,16-17,19-20,26,28H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1

2.1.3 InChI Key

XSFJVAJPIHIPKU-XWCQMRHXSA-N

2.1.4 Canonical SMILES

CC1(OC2CC3C4CC(C5=CC(=O)C=CC5(C4C(CC3(C2(O1)C(=O)CO)C)O)C)F)C

2.1.5 Isomeric SMILES

C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)C[C@@H](C5=CC(=O)C=C[C@]35C)F)O

2.2 Other Identifiers

2.2.1 UNII

78M02AA8KF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6 Alpha-fluorodihydroxy-16 Alpha,17 Alpha-isopropylidenedioxy-1,4-pregnadiene-3,20- Dione

2. 6alpha-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16, 17-acetal With Acetone

3. Aerobid

4. Aerospan

5. Apo-flunisolide

6. Flunisolide 21-acetate

7. Flunisolide Acetate

8. Flunisolide Anhydrous

9. Flunisolide Hemihydrate

10. Flunisolide Hemihydrate, (6alpha,11beta,16alpha)-isomer

11. Flunisolide Hfa

12. Flunisolide Hydrofluoroalkane

13. Flunisolide, (6beta,11beta,16alpha)-isomer

14. Inhacort

15. Nasalide

16. Nasarel

17. Ratio-flunisolide

18. Rhinalar

19. Rs-1320

20. Rs-3999

21. Rs1320

22. Syntaris

2.3.2 Depositor-Supplied Synonyms

1. 3385-03-3

2. Aerobid

3. Rhinalar

4. Synaclyn

5. Flunisolide Anhydrous

6. Nasarel

7. Syntaris

8. Flunisolide Hfa

9. Nasalide

10. Aerospan

11. Bronalide

12. Flunisolide [inn]

13. Flunisolida

14. Flunisolidum

15. Aerospan Hfa

16. Lunis

17. Rs-3999

18. Chebi:5106

19. Flunisolide Hemihydrate

20. Nisolid

21. Soluzione

22. Mls002153928

23. 78m02aa8kf

24. Pregna-1,4-diene-3,20-dione,6-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-,(6a,11b,16a)-

25. Aerobid M

26. Dsstox_cid_25534

27. Dsstox_rid_80936

28. Dsstox_gsid_45534

29. (1s,2s,4r,8s,9s,11s,12s,13r,19s)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

30. Flunisolide [anhydrous]

31. Cas-3385-03-3

32. Nsc-757871

33. Flunisolidum [inn-latin]

34. Flunisolida [inn-spanish]

35. Syntaris Hayfever

36. Ncgc00016983-01

37. Lunisolide Anhydrous

38. Prestwick_223

39. Einecs 222-193-2

40. Rs 3999

41. Flunisolide [mi]

42. Prestwick0_000643

43. Prestwick1_000643

44. Prestwick2_000643

45. Prestwick3_000643

46. Schembl4351

47. Chembl1512

48. Unii-78m02aa8kf

49. Bspbio_000645

50. Flunisolide [who-dd]

51. 6alpha-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16, 17-acetal With Acetone

52. Spbio_002566

53. Bpbio1_000711

54. Gtpl7076

55. Dtxsid1045534

56. Hms1570a07

57. Hms2097a07

58. Hms2236a06

59. Hms3259l10

60. Hms3714a07

61. Hy-b1121

62. Zinc4097305

63. Tox21_110725

64. Bdbm50248007

65. Akos025402038

66. Tox21_110725_1

67. Ac-3514

68. Bcp9000696

69. Ccg-220643

70. Cs-4713

71. Db00180

72. Nc00716

73. 6-fluoro-11,21-dihydroxy-16,17-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione

74. Ncgc00179492-01

75. Ncgc00179492-03

76. Pregna-1,4-diene-3,20-dione, 6-alpha-fluoro-11-beta,16-alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

77. Pregna-1,4-diene-3,20-dione, 6-fluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6alpha,11beta,16alpha)-

78. Smr001233272

79. Flunisolide 100 Microg/ml In Acetonitrile

80. F0437

81. (6a,11b,16a)-6-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione

82. C07005

83. D78324

84. 385f033

85. Q3746835

86. Brd-k49577446-001-03-1

87. (1s,2s,4r,8s,9s,11s,12s,13r,19s)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one

88. 6.alpha.-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone

89. 6alpha-fluoro-11beta,21-dihydroxy-16alpha,17alpha-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione

90. Pregna-1,4-diene-3,20-dione, 6-fluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))- (6.alpha.,11.beta.,16.alpha.)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₁FO₆
Molecular Weight	434.5 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	434.21046687 g/mol
Monoisotopic Mass	434.21046687 g/mol
Topological Polar Surface Area	93.1 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	910
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 4
Drug Name	Aerospan hfa
PubMed Health	Flunisolide
Drug Classes	Anti-Inflammatory
Drug Label	Flunisolide hemihydrate, the active component of AEROSPANTM (flunisolide HFA, 80 mcg) Inhalation Aerosol, is a corticosteroid having the chemical name 6-Fluoro-11, 16, 17, 21 tetrahydroxylpregna-1, 4-diene-3, 20-dione cyclic-16, 17-acetal wi...
Active Ingredient	Flunisolide
Dosage Form	Aerosol, metered
Route	Inhalation
Strength	0.078mg/inh
Market Status	Prescription
Company	Meda Pharms

2 of 4
Drug Name	Flunisolide
Active Ingredient	Flunisolide
Dosage Form	Spray, metered
Route	Nasal
Strength	0.025mg/spray; 0.029mg/spray
Market Status	Prescription
Company	Apotex; Hi Tech Pharma; Bausch And Lomb

3 of 4
Drug Name	Aerospan hfa
PubMed Health	Flunisolide
Drug Classes	Anti-Inflammatory
Drug Label	Flunisolide hemihydrate, the active component of AEROSPANTM (flunisolide HFA, 80 mcg) Inhalation Aerosol, is a corticosteroid having the chemical name 6-Fluoro-11, 16, 17, 21 tetrahydroxylpregna-1, 4-diene-3, 20-dione cyclic-16, 17-acetal wi...
Active Ingredient	Flunisolide
Dosage Form	Aerosol, metered
Route	Inhalation
Strength	0.078mg/inh
Market Status	Prescription
Company	Meda Pharms

4 of 4
Drug Name	Flunisolide
Active Ingredient	Flunisolide
Dosage Form	Spray, metered
Route	Nasal
Strength	0.025mg/spray; 0.029mg/spray
Market Status	Prescription
Company	Apotex; Hi Tech Pharma; Bausch And Lomb

4.2 Drug Indication

For the maintenance treatment of asthma as a prophylactic therapy.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Flunisolide is a synthetic corticosteroid. It is administered either as an oral metered-dose inhaler for the treatment of asthma or as a nasal spray for treating allergic rhinitis. Corticosteroids are naturally occurring hormones that prevent or suppress inflammation and immune responses. When given as an intranasal spray, flunisolide reduces watery nasal discharge (rhinorrhea), nasal congestion, postnasal drip, sneezing, and itching oat the back of the throat that are common allergic symptoms.

5.2 MeSH Pharmacological Classification

Anti-Asthmatic Agents

Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

FLUNISOLIDE ANHYDROUS

5.3.2 FDA UNII

78M02AA8KF

5.3.3 Pharmacological Classes

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

5.4 ATC Code

R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AD - Corticosteroids

R01AD04 - Flunisolide

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03B - Other drugs for obstructive airway diseases, inhalants

R03BA - Glucocorticoids

R03BA03 - Flunisolide

5.5 Absorption, Distribution and Excretion

Absorption

Absorbed rapidly

5.6 Metabolism/Metabolites

Primarily hepatic, converted to the S beta-OH metabolite.

5.7 Biological Half-Life

1.8 hours

5.8 Mechanism of Action

Flunisolide is a glucocorticoid receptor agonist. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Flunisolide binds to plasma transcortin, and it becomes active when it is not bound to transcortin.