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    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
    Flumethasone
    An anti-inflammatory glucocorticoid used in veterinary practice.
    1 2D Structure

    Flumethasone

    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 Weight 410.5 g/mol
    Molecular Formula C22H28F2O5
    XLogP31.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass410.19048031 g/mol
    Monoisotopic Mass410.19048031 g/mol
    Topological Polar Surface Area94.8 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity839
    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 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.

    API Reference Price

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    12-Jan-2021
    05-Aug-2024
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