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Fluorodexamethazone

Chemistry

Chemistry

Also known as: Flumetasone, 2135-17-3, Aniprime, Flucorticin, Flumethason, Anaprime

Molecular Formula

C₂₂H₂₈F₂O₅

Molecular Weight

410.5 g/mol

InChI Key

WXURHACBFYSXBI-GQKYHHCASA-N

FDA UNII

LR3CD8SX89

An anti-inflammatory glucocorticoid used in veterinary practice.

1 2D Structure

Fluorodexamethazone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

2.1.2 InChI

InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1

2.1.3 InChI Key

WXURHACBFYSXBI-GQKYHHCASA-N

2.1.4 Canonical SMILES

CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)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)CO)O)C)O)F)C)F

2.2 Other Identifiers

2.2.1 UNII

LR3CD8SX89

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fluorodexamethasone

2.3.2 Depositor-Supplied Synonyms

1. Flumetasone

2. 2135-17-3

3. Aniprime

4. Flucorticin

5. Flumethason

6. Anaprime

7. Methagon

8. Fluvet

9. Cortexilar

10. Flumetasona

11. Flumetasonum

12. Rs 2177

13. Flumetasone [inn]

14. Rs-2177

15. Flumethasone [usan]

16. 6alpha,9-difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione

17. Nsc-54702

18. 6alpha,9alpha-difluoro-16alpha-methylprednisolone

19. U-10974

20. U-10,974

21. Lr3cd8sx89

22. Mls000028618

23. Chebi:34764

24. Flumetasone (inn)

25. (6s,8s,9r,10s,11s,13s,14s,16r,17r)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

26. Flumethasone (usan)

27. Smr000058690

28. Dsstox_cid_25365

29. Dsstox_rid_80828

30. Pregna-1,4-diene-3,20-dione,6,9-difluoro-11,17,21-trihydroxy-16-methyl-, (6a,11b,16a)-

31. Dsstox_gsid_45365

32. Flumethasonum

33. 6alpha-fluorodexamethasone

34. Mfcd00056464

35. Flucort (veterinary)

36. 6.alpha.-fluorodexamethasone

37. Nsc 54702

38. Flumetasonum [inn-latin]

39. 6-alpha-fluorodexamethasone

40. Flumetasona [inn-spanish]

41. Nsc54702

42. Ncgc00016604-01

43. Prestwick_229

44. Cas-2135-17-3

45. Einecs 218-370-9

46. Brn 5645455

47. Opera_id_1501

48. Prestwick0_000734

49. Prestwick1_000734

50. Prestwick2_000734

51. Prestwick3_000734

52. Flumethasone [mi]

53. Unii-lr3cd8sx89

54. 6alpha-fluoro-dexamethasone

55. Schembl4046

56. Bspbio_000688

57. Flumetasone [who-dd]

58. Mls001077306

59. Spbio_002627

60. Bpbio1_000758

61. 6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

62. Chembl1201392

63. Dtxsid2045365

64. Flumethasone [green Book]

65. Hms1570c10

66. Hms2097c10

67. Hms2234b11

68. Hms3714c10

69. (6s,8s,9r,10s,11s,13s,14s,16r,17r)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-3-one

70. Amy38487

71. Hy-b1051

72. Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,17,21-trihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-

73. Zinc3983936

74. Tox21_110518

75. S4088

76. Akos005256462

77. Akos015895435

78. Tox21_110518_1

79. Ac-2069

80. Ccg-220734

81. Cs-4573

82. Db00663

83. Flumethasone 100 Microg/ml In Methanol

84. Smp1_000127

85. Ncgc00021761-03

86. Ncgc00021761-05

87. Ncgc00021761-06

88. (6alpha,11beta,16alpha)-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

89. As-12534

90. Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,17,21-trihydroxy-16alpha-methyl-(van)

91. Flumethasone 100 Microg/ml In Acetonitrile

92. F0945

93. D04208

94. Ec 218-370-9

95. T72075

96. 135f173

97. A855571

98. Sr-01000003144

99. Q-101387

100. Q4383636

101. Sr-01000003144-3

102. Brd-k61496577-001-03-8

103. Brd-k61496577-001-20-2

104. 6.alpha., 9.alpha.-difluoro-16.alpha.-methylprednisolone

105. (6?,11?,16?)-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

106. (1r,2s,8s,10s,11s,13r,14r,15s,17s)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-5-one

107. (6s,9r,10s,11s,13s,16r,17r)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

108. 6.alpha., 9-difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methylpregna-1, 4-diene-3,20-dione

109. 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dione

110. 6alpha,9-difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione (flumetasone)

111. Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,17, 21-trihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-

112. Pregna-1,4-diene-3,20-dione, 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methyl-

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₈F₂O₅
Molecular Weight	410.5 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	410.19048031 g/mol
Monoisotopic Mass	410.19048031 g/mol
Topological Polar Surface Area	94.8 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	839
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 Indication

For the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin conditions

5 Pharmacology and Biochemistry

5.1 Pharmacology

Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.

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.)

5.3 ATC Code

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AB - Corticosteroids, moderately potent (group ii)

D07AB03 - Flumetasone

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07X - Corticosteroids, other combinations

D07XB - Corticosteroids, moderately potent, other combinations

D07XB01 - Flumetasone

5.4 Absorption, Distribution and Excretion

Absorption

Minimal if applied topically

5.5 Metabolism/Metabolites

Primarily hepatic

5.6 Mechanism of Action

Flumethasone is a glucocorticoid receptor agonist. This complex binds to the nucleus causing a variety of genetic activation and repressions. 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. Flumethasone binds to plasma transcortin, and it becomes active when it is not bound to transcortin.