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1,4-PREGNADIEN-6ALPHA,9ALPHA-DIFLUORO-11BETA,16ALPHA,17,21-TETROL-3,20-DIONE 16,17-ACETONIDE 21-ACETATE
Also known as: 356-12-7, Lidex, Fluocinolide, Fluocinolone acetonide acetate, Vanos, Lonide
Molecular Formula
C26H32F2O7
Molecular Weight
494.5  g/mol
InChI Key
WJOHZNCJWYWUJD-IUGZLZTKSA-N
FDA UNII
2W4A77YPAN

A topical glucocorticoid used in the treatment of ECZEMA.
Fluocinonide is a Corticosteroid. The mechanism of action of fluocinonide is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

1,4-PREGNADIEN-6ALPHA,9ALPHA-DIFLUORO-11BETA,16ALPHA,17,21-TETROL-3,20-DIONE 16,17-ACETONIDE 21-ACETATE

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] acetate
2.1.2 InChI
InChI=1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1
2.1.3 InChI Key
WJOHZNCJWYWUJD-IUGZLZTKSA-N
2.1.4 Canonical SMILES
CC(=O)OCC(=O)C12C(CC3C1(CC(C4(C3CC(C5=CC(=O)C=CC54C)F)F)O)C)OC(O2)(C)C
2.1.5 Isomeric SMILES
CC(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@]4([C@H]3C[C@@H](C5=CC(=O)C=C[C@@]54C)F)F)O)C)OC(O2)(C)C
2.2 Other Identifiers
2.2.1 UNII
2W4A77YPAN
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acetonide 21-acetate, Fluocinolone

2. Fapg, Fluocinonide

3. Fluocinolide

4. Fluocinolone Acetonide 21 Acetate

5. Fluocinolone Acetonide 21-acetate

6. Fluocinonide Fapg

7. Klariderm

8. Lidemol

9. Lidex

10. Lyderm

11. Metosyn

12. Novoter

13. Tiamol

14. Topsym

15. Topsyn

16. Topsyne

2.3.2 Depositor-Supplied Synonyms

1. 356-12-7

2. Lidex

3. Fluocinolide

4. Fluocinolone Acetonide Acetate

5. Vanos

6. Lonide

7. Fluocinolide Acetate

8. Fluonex

9. Lidex-e

10. Metosyn

11. Topsyn

12. Fluocinonidum [inn-latin]

13. Fluocinonide Emulsified Base

14. Fluocinonido [inn-spanish]

15. Fluocinolone Acetonide 21-acetate

16. Lidex E

17. Lyderm

18. 2w4a77ypan

19. Mls000028476

20. Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-,(6a,11b,16a)-

21. Fluocinonido

22. Fluocinonidum

23. Smr000058331

24. Dsstox_cid_25307

25. Dsstox_rid_80793

26. Dsstox_gsid_45307

27. C26h32f2o7

28. Nsc-101791

29. Fluocinonide [usan:ban:inn:jan]

30. Vanos (tn)

31. Einecs 206-597-6

32. Lidex (tn)

33. Unii-2w4a77ypan

34. Nsc 101791

35. Ncgc00016436-01

36. Cas-356-12-7

37. Fluocinonide(vanos)

38. Prestwick_1066

39. Fluocinonide (vanos)

40. 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, Cyclic 16,17-acetal With Acetone, 21-acetate

41. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6alpha,11beta,16alpha)-

42. Fluocinonide [usan:usp:inn:ban:jan]

43. Opera_id_1780

44. Prestwick0_000774

45. Prestwick1_000774

46. Prestwick2_000774

47. Prestwick3_000774

48. Fluocinonide [mi]

49. Fluocinonide [inn]

50. Fluocinonide [jan]

51. Fluocinonide [usan]

52. Schembl4262

53. Chembl1501

54. Fluocinonide [vandf]

55. Bspbio_000848

56. Fluocinonide [mart.]

57. Pregna-1,4-diene-3,20-dione, 6-alpha, 9-difluoro-11-beta,16-alpha,17,21-tetrahydroxy-, Cyclic17-acetal With Acetone, 21-acetate

58. Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone, 21-acetate

59. Fluocinonide [usp-rs]

60. Fluocinonide [who-dd]

61. Spbio_002787

62. Bpbio1_000934

63. Chebi:5109

64. Gtpl7078

65. Dtxsid8045307

66. Fluocinonide (jp17/usp/inn)

67. Fluocinonide, >=98% (hplc)

68. Fluocinonide [orange Book]

69. Hms1570k10

70. Hms2097k10

71. Hms2234h04

72. Hms3259n05

73. Hms3714k10

74. Fluocinonide [usp Impurity]

75. 6.alpha.,9-difluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, Cyclic 16,17-acetal With Acetone, 21-acetate

76. Hy-b0485

77. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6.alpha.,11.beta.,16.alpha.)-

78. Zinc3977978

79. Tox21_110438

80. S2608

81. Akos015896516

82. Tox21_110438_1

83. Ac-2071

84. Bcp9000697

85. Ccg-220774

86. Db01047

87. Nc00621

88. Ncgc00022398-03

89. Ncgc00022398-05

90. Bs-17093

91. C07007

92. D00325

93. 356f127

94. Sr-01000003097

95. Q5462791

96. Sr-01000003097-3

97. W-106660

98. Brd-k57886322-001-03-4

99. Brd-k57886322-001-12-5

100. Fluocinonide, United States Pharmacopeia (usp) Reference Standard

101. 2-((2s,6as,6br,7s,8as,8bs,11ar,12as,12bs)-2,6b-difluoro-7-hydroxy-6a,8a,10,10-tetramethyl-4-oxo-1,2,4,6a,6b,7,8,8a,11a,12,12a,12b-dodecahydro-8bh-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl Acetate

102. 2-[(1s,2s,4r,8s,9s,11s,12r,13s,19s)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl Acetate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 494.5 g/mol
Molecular Formula C26H32F2O7
XLogP33.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass494.21160968 g/mol
Monoisotopic Mass494.21160968 g/mol
Topological Polar Surface Area99.1 Ų
Heavy Atom Count35
Formal Charge0
Complexity1070
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 8  
Drug NameFluocinonide
PubMed HealthFluocinonide (On the skin)
Drug ClassesCorticosteroid, Strong
Drug LabelFluocinonide Cream 0.1% contains fluocinonide, a synthetic corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents. Fluocinonide h...
Active IngredientFluocinonide
Dosage FormOintment; Cream; Gel; Solution
RouteTopical
Strength0.05%; 0.1%
Market StatusPrescription
CompanyTeva; Taro; Fougera; Glenmark Generics; Fougera Pharms; G And W Labs; Perrigo Israel

2 of 8  
Drug NameFluocinonide emulsified base
PubMed HealthFluocinonide (On the skin)
Drug ClassesCorticosteroid, Strong
Drug LabelVANOS (fluocinonide) Cream, 0.1% contains fluocinonide, a synthetic corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents. Fluoc...
Active IngredientFluocinonide
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyTeva; Taro; Fougera Pharms

3 of 8  
Drug NameLidex
PubMed HealthFluocinonide (On the skin)
Drug ClassesCorticosteroid, Strong
Active IngredientFluocinonide
Dosage FormSolution
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyCnty Line Pharms

4 of 8  
Drug NameVanos
Active IngredientFluocinonide
Dosage FormCream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyMedicis

5 of 8  
Drug NameFluocinonide
PubMed HealthFluocinonide (On the skin)
Drug ClassesCorticosteroid, Strong
Drug LabelFluocinonide Cream 0.1% contains fluocinonide, a synthetic corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents. Fluocinonide h...
Active IngredientFluocinonide
Dosage FormOintment; Cream; Gel; Solution
RouteTopical
Strength0.05%; 0.1%
Market StatusPrescription
CompanyTeva; Taro; Fougera; Glenmark Generics; Fougera Pharms; G And W Labs; Perrigo Israel

6 of 8  
Drug NameFluocinonide emulsified base
PubMed HealthFluocinonide (On the skin)
Drug ClassesCorticosteroid, Strong
Drug LabelVANOS (fluocinonide) Cream, 0.1% contains fluocinonide, a synthetic corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents. Fluoc...
Active IngredientFluocinonide
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyTeva; Taro; Fougera Pharms

7 of 8  
Drug NameLidex
PubMed HealthFluocinonide (On the skin)
Drug ClassesCorticosteroid, Strong
Active IngredientFluocinonide
Dosage FormSolution
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyCnty Line Pharms

8 of 8  
Drug NameVanos
Active IngredientFluocinonide
Dosage FormCream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyMedicis

4.2 Drug Indication

A topical anti-inflammatory product for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It mediates its effects to relieve itching, redness, dryness, crusting, scaling, inflammation, and discomfort associated with inflammatory skin conditions.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

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


Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)


Anti-Allergic Agents

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FLUOCINONIDE
5.3.2 FDA UNII
2W4A77YPAN
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

C05A - Agents for treatment of hemorrhoids and anal fissures for topical use

C05AA - Corticosteroids

C05AA11 - Fluocinonide


D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC08 - Fluocinonide


5.5 Absorption, Distribution and Excretion

Absorption

The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle, the integrity of the epidermal barrier, and the use of occlusive dressings. In general, percutaneous absorption is minimal.


Route of Elimination

Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.


5.6 Mechanism of Action

Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. Fluocinonide binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally 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. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.


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  • CREAM;TOPICAL - 0.05% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
  • OINTMENT;TOPICAL - 0.05%
  • SOLUTION;TOPICAL - 0.05%
  • CREAM;TOPICAL - 0.05% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
  • CREAM;TOPICAL - 0.1%
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