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Fludrocortisone Acetate
Also known as: 514-36-3, Scherofluron, Cortineff, Fludrocortisone 21-acetate, Florinef acetate, Alflorone acetate
Molecular Formula
C23H31FO6
Molecular Weight
422.5  g/mol
InChI Key
SYWHXTATXSMDSB-GSLJADNHSA-N
FDA UNII
V47IF0PVH4

Fludrocortisone Acetate is the acetate salt of a synthetic fluorinated corticosteroid with antiinflammatory and antiallergic activities. As a glucocorticoid-receptor agonist, fludrocortisone binds to cytoplasmic receptors, translocates to the nucleus, and subsequently initiates the transcription of glucocorticoid-responsive genes such as lipocortins to inhibit phospholipase A2 (PLA2). Inhibition of PLA2 activity prevents the release of arachidonic acid, a precursor of eicosanoids such as prostaglandins and leukotrienes; eicosanoids are important mediators in the pro-inflammatory response mechanism. As a mineralocorticoid-receptor agonist, this agent stimulates Na+ reabsorption and water retention and K+ and H+ secretion in the distal tubules and collecting ducts of the kidney.
1 2D Structure

Fludrocortisone Acetate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
2.1.2 InChI
InChI=1S/C23H31FO6/c1-13(25)30-12-19(28)22(29)9-7-16-17-5-4-14-10-15(26)6-8-20(14,2)23(17,24)18(27)11-21(16,22)3/h10,16-18,27,29H,4-9,11-12H2,1-3H3/t16-,17-,18-,20-,21-,22-,23-/m0/s1
2.1.3 InChI Key
SYWHXTATXSMDSB-GSLJADNHSA-N
2.1.4 Canonical SMILES
CC(=O)OCC(=O)C1(CCC2C1(CC(C3(C2CCC4=CC(=O)CCC43C)F)O)C)O
2.1.5 Isomeric SMILES
CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)CC[C@@]43C)F)O)C)O
2.2 Other Identifiers
2.2.1 UNII
V47IF0PVH4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9 Alpha-fluorocortisol Acetate

2. 9-fluoro-11beta,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate

3. Cortineff

4. Florinef

5. Fludrocortisone 21-acetate

6. Fluorocortisol Acetate

2.3.2 Depositor-Supplied Synonyms

1. 514-36-3

2. Scherofluron

3. Cortineff

4. Fludrocortisone 21-acetate

5. Florinef Acetate

6. Alflorone Acetate

7. Fluorocortisol Acetate

8. Cortef-f

9. F-cortef Acetate

10. Fluorocortisone Acetate

11. Fluohydrocortisone Acetate

12. Fludrocortisoneacetate

13. 9alpha-fluorohydrocortisone Acetate

14. Nsc-15186

15. U 4845

16. 9alpha-fluorohydrocortisone 21-acetate

17. V47if0pvh4

18. 514-36-3 (acetate)

19. Chebi:5102

20. 2-((8s,9r,10s,11s,13s,14s,17r)-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl Acetate

21. Pregn-4-ene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-,(11b)-

22. [2-[(8s,9r,10s,11s,13s,14s,17r)-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Acetate

23. (11beta)-9-fluoro-11,17-dihydroxy-3,20-dioxopregn-4-en-21-yl Acetate

24. 9alpha-fluoro-11beta,17alpha,21-trihydroxy-pregn-4-en-3,20-dione 21-acetate

25. Mls002638417

26. Fludrocortisone (acetate)

27. Mfcd00864160

28. Unii-v47if0pvh4

29. Fludrocortisone Acetate [jan]

30. 9-fluoro-11-beta,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate

31. Fludrocortisonacetat

32. Cortisol, 9-fluoro-, 21-acetate

33. Fludrocortisone Acetate [usp:jan]

34. 9-alpha-fluorohydrocortisone Acetate

35. Einecs 208-180-4

36. Nsc 15186

37. Fludrocortisoni Acetas

38. Fludrocortisone-acetate

39. 9-alpha-fluorohydrocortisone-21-acetate

40. Brn 2067486

41. Florinef Acetate (tn)

42. 9a-fluorcortisol Acetate

43. 9a-fluorocortisol Acetate

44. Prestwick0_000281

45. Prestwick1_000281

46. Prestwick2_000281

47. 9-fluoro-11beta,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate

48. 9a-fludrocortisone Acetate

49. Acetic Acid Fludrocortisone

50. Schembl4737

51. Corticosterone, 9-fluoro-17-hydroxy-, 21-acetate

52. Spbio_002401

53. 9.alpha.-fluorocortisol Acetate

54. Chembl1201010

55. Dtxsid2023062

56. Fludrocortisone Acetate, >=98%

57. Hy-b1203a

58. Fluorhydrocortisone Acetate

59. Hms1568j04

60. Nsc15186

61. Zinc3977990

62. Fludrocortisone Acetate (jp17/usp)

63. Lmst02030122

64. S3659

65. 9.alpha.-fluorohydrocortisone Acetate

66. Akos015963145

67. Ccg-268914

68. Cs-4833

69. Ds-3879

70. Fludrocortisone Acetate [mart.]

71. Fludrocortisone Acetate [vandf]

72. Fludrocortisone Acetate [usp-rs]

73. Fludrocortisone Acetate [who-dd]

74. Fludrocortisone Acetate [who-ip]

75. Pregn-4-ene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-, (11.beta.)-

76. Fludrocortisone 21-acetate [mi]

77. 9.alpha.-fluorohydrocortisone 21-acetate

78. 9.alpha.-fluorohydrocortisone-21-acetate

79. Ac-18903

80. Fludrocortisone Acetate [orange Book]

81. Fludrocortisoni Acetas [who-ip Latin]

82. Fludrocortisone Acetate [ep Monograph]

83. C08186

84. D00986

85. Fludrocortisone Acetate [usp Monograph]

86. Q-201121

87. 9

88. A-fludrocortisone Acetate;9

89. A-fluorcortisol Acetate

90. Fludrocortisone Acetate 100 Microg/ml In Acetonitrile

91. Q27106657

92. Wln: L E5 B666 Ov Mutj A1 Bf Cq E1 Fv1ov1 Fq

93. 9-fluoro-11beta,17-dihydroxy-3,20-dioxopregn-4-en-21-yl Acetate

94. Pregn-4-ene-3, 9-fluoro-11.beta.,17,21-trihydroxy-, 21-acetate

95. 9-fluoro-11

96. A, 17, 21-trihydroxypregn-4-ene-3, 20-dione 21-acetate

97. Fludrocortisone Acetate, European Pharmacopoeia (ep) Reference Standard

98. Fludrocortisone Acetate, United States Pharmacopeia (usp) Reference Standard

99. Pregn-4-ene-3, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-, (11.beta.)-

100. Pregn-4-ene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-, 21-acetate

101. Pregn-4-ene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-, 21-acetate

102. 9-fluoro-11.beta.,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate

103. Pregn-4-ene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-, (11beta)-

104. [2-[(9r,10s,11s,13s,17r)-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Acetate

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 422.5 g/mol
Molecular Formula C23H31FO6
XLogP31.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass422.21046687 g/mol
Monoisotopic Mass422.21046687 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count30
Formal Charge0
Complexity838
Isotope Atom Count0
Defined Atom Stereocenter Count7
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 NameFludrocortisone acetate
PubMed HealthFludrocortisone Acetate (By mouth)
Drug ClassesDiagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent
Drug LabelFludrocortisone Acetate Tablets, USP contains fludrocortisone acetate, a synthetic adrenocortical steroid possessing very potent mineralocorticoid properties and high glucocorticoid activity; it is used only for its mineralocorticoid effects. The che...
Active IngredientFludrocortisone acetate
Dosage FormTablet
RouteOral
Strength0.1mg
Market StatusPrescription
CompanyHikma Pharms; Impax Labs; Barr

2 of 2  
Drug NameFludrocortisone acetate
PubMed HealthFludrocortisone Acetate (By mouth)
Drug ClassesDiagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent
Drug LabelFludrocortisone Acetate Tablets, USP contains fludrocortisone acetate, a synthetic adrenocortical steroid possessing very potent mineralocorticoid properties and high glucocorticoid activity; it is used only for its mineralocorticoid effects. The che...
Active IngredientFludrocortisone acetate
Dosage FormTablet
RouteOral
Strength0.1mg
Market StatusPrescription
CompanyHikma Pharms; Impax Labs; Barr

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