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    Cortisone

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: Cortisone 21-acetate, 50-04-4, Cortone acetate, Incortin, Biocort acetate, Artriona
    Molecular Formula
    C23H30O6
    Molecular Weight
    402.5  g/mol
    InChI Key
    ITRJWOMZKQRYTA-RFZYENFJSA-N
    FDA UNII
    883WKN7W8X
    A naturally occurring glucocorticoid that has been used in replacement therapy for ADRENAL INSUFFICIENCY and as an anti-inflammatory agent. Cortisone itself is inactive; it is converted in the liver to the active metabolite HYDROCORTISONE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p726)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-[(8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
    2.1.2 InChI
    InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-17,20,28H,4-9,11-12H2,1-3H3/t16-,17-,20+,21-,22-,23-/m0/s1
    2.1.3 InChI Key
    ITRJWOMZKQRYTA-RFZYENFJSA-N
    2.1.4 Canonical SMILES
    CC(=O)OCC(=O)C1(CCC2C1(CC(=O)C3C2CCC4=CC(=O)CCC34C)C)O
    2.1.5 Isomeric SMILES
    CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC(=O)[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    883WKN7W8X
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 17-hydroxy-3,11,20-trioxopregn-4-en-21-yl Acetate

    2. Adreson

    3. Cortisone

    4. Cortone Acetate

    2.3.2 Depositor-Supplied Synonyms

    1. Cortisone 21-acetate

    2. 50-04-4

    3. Cortone Acetate

    4. Incortin

    5. Biocort Acetate

    6. Artriona

    7. Cortadren

    8. Scheroson

    9. Cortisyl

    10. Adreson

    11. Irisone Acetate

    12. Cortelan

    13. Cortistab

    14. Ricortex

    15. Cortogen Acetate

    16. Compound E Acetate

    17. Pregn-4-ene-3,11,20-trione, 21-(acetyloxy)-17-hydroxy-

    18. Cortisone Monoacetate

    19. Nsc 49420

    20. Cortisone, 21-acetate

    21. Cortilen

    22. Cortisone Aceticum

    23. 11-dehydro-17-hydroxycorticosterone-21-acetate

    24. 11-dehydro-17-hydroxycorticosterone Acetate

    25. 17,21-dihydroxypregn-4-ene-3,11,20-trione 21-acetate

    26. Nsc-49420

    27. 883wkn7w8x

    28. Chebi:3897

    29. Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-, 21-acetate

    30. Cortisone (acetate)

    31. Ncgc00021191-07

    32. 17-hydroxy-3,11,20-trioxopregn-4-en-21-yl Acetate

    33. Dsstox_cid_2858

    34. Dsstox_rid_76761

    35. Dsstox_gsid_22858

    36. 17,21-dihydroxypregn-4-ene-3,11,20-trione-21-acetate

    37. 17alpha,21-dihydroxypregn-4-ene-3,11,20-trione Acetate

    38. Cas-50-04-4

    39. [2-[(8s,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Acetate

    40. 2-((8s,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl Acetate

    41. Smr000059124

    42. Ccris 3661

    43. Cortisone Acetate (cortone)

    44. Einecs 200-006-5

    45. Unii-883wkn7w8x

    46. Cortisoneacetate

    47. Cortisone Acetate [usp:jan]

    48. Acetate Cortisone

    49. Cortisyl Artriona

    50. Component Of Neosone

    51. Mfcd00003609

    52. Neosone (salt/mix)

    53. 21-(acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trione

    54. Cortisone-21-acetate

    55. 21-acetoxy-17,alpha-hydroxy-3,11,20-triketopregnene-4

    56. 21-acetoxy-17,alpha-hydroxypregn-4-ene-3,11,20-trione

    57. Cortone Acetate (tn)

    58. 4-pregnene-17,alpha,21-diol-3,11,20-trione 21-acetate

    59. Schembl4501

    60. Chembl1650

    61. Lopac0_000271

    62. Mls000069478

    63. Mls002207136

    64. Mls002548859

    65. 21-acetoxy-4-pregnen-17alpha-ol-3,11,20-trione

    66. Cortisone Acetate [jan]

    67. Cortisone Acetate (jp17/usp)

    68. Dtxsid0022858

    69. Cortisone 21-acetate, >=99%

    70. Cortisone Acetate [vandf]

    71. Cortisone Aceticum [hpus]

    72. Cortisone Acetate [mart.]

    73. 17alpha,21-dihydroxy-4-pregnene-3,11,20-trione 21-acetate

    74. Hms2235d24

    75. Hms3259n19

    76. Hms3260h04

    77. Cortisone Acetate [usp-rs]

    78. Cortisone Acetate [who-dd]

    79. Bcp08487

    80. Cortisone 21-acetate [mi]

    81. Nsc49420

    82. Zinc3875334

    83. Tox21_113482

    84. Tox21_500271

    85. Bdbm50455157

    86. Hy-17461a

    87. Lmst02030120

    88. Akos005267225

    89. Tox21_113482_1

    90. Ac-6827

    91. Ccg-204366

    92. Cortisone Acetate [orange Book]

    93. Cs-1742

    94. Db01380

    95. Lp00271

    96. Nc00677

    97. Sdccgsbi-0050259.p002

    98. Cortisone Acetate [ep Monograph]

    99. Cortisone Acetate [usp Monograph]

    100. Ncgc00021191-03

    101. Ncgc00021191-06

    102. Ncgc00021191-08

    103. Ncgc00021191-09

    104. Ncgc00021191-16

    105. Ncgc00260956-01

    106. [2-[(8s,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] Acetate

    107. 2-((1s,10s,11s,15s,2r,14r)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0 .0<2,7>.0<11,15>]heptadec-6-en-14-yl)-2-oxoethyl Acetate

    108. As-13692

    109. Cortisone Acetate 100 Microg/ml In Methanol

    110. Eu-0100271

    111. S2559

    112. C08173

    113. C90609

    114. D00973

    115. Ab00384283-08

    116. Ab00384283_09

    117. Cortisone Acetate 100 Microg/ml In Acetonitrile

    118. 003c609

    119. W-105993

    120. Brd-k86161929-001-13-3

    121. Hydrocortisone Acetate Impurity D [ep Impurity]

    122. Pregn-4-ene-3,20-trione, 21-(acetyloxy)-17-hydroxy-

    123. 17-hydroxy-3,11,20-trioxopregn-4-en-21-yl Acetate #

    124. 21-acetoxy-17.alpha.-hydroxy-3,11,20-triketopregnene-4

    125. 21-acetoxy-17.alpha.-hydroxypregn-4-ene-3,11,20-trione

    126. 4-pregnen-17.alpha.,21-diol-3,11,20-trione 21-acetate

    127. Pregn-4-ene-3,20-trione, 17,21-dihydroxy-, 21-acetate

    128. 4-pregnene-17.alpha.,21-diol-3,11,20-trione 21-acetate

    129. Cortisone Acetate, European Pharmacopoeia (ep) Reference Standard

    130. Cortisone Acetate, United States Pharmacopeia (usp) Reference Standard

    131. Cortisone Acetate, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 402.5 g/mol
    Molecular Formula C23H30O6
    XLogP32.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count4
    Exact Mass402.20423867 g/mol
    Monoisotopic Mass402.20423867 g/mol
    Topological Polar Surface Area97.7 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity827
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    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 NameCortisone acetate
    PubMed HealthCortisone Acetate (By mouth)
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant
    Drug LabelGlucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from the gastrointestinal tract.Cortisone acetate is a white or practically white, odorless, crystalline powder. It is stable in air. It i...
    Active IngredientCortisone acetate
    Dosage FormTablet
    RouteOral
    Strength25mg
    Market StatusPrescription
    CompanyHikma Pharms

    2 of 2  
    Drug NameCortisone acetate
    PubMed HealthCortisone Acetate (By mouth)
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant
    Drug LabelGlucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from the gastrointestinal tract.Cortisone acetate is a white or practically white, odorless, crystalline powder. It is stable in air. It i...
    Active IngredientCortisone acetate
    Dosage FormTablet
    RouteOral
    Strength25mg
    Market StatusPrescription
    CompanyHikma Pharms

    4.2 Drug Indication

    Cortisone acetate is indicated to treat a wide variety of endocrine, rheumatic, collagen, dermatologic, allergic, ophthalmic, respiratory, hematologic, neoplastic, edematous, and gastrointestinal diseases and disorders.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. The duration of action is moderate as it is generally given once daily. Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces. Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.

    5.2 MeSH Pharmacological Classification

    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 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.4 Absorption, Distribution and Excretion

    Route of Elimination

    Corticosteroids are eliminated predominantly in the urine.

    Clearance

    Data regarding the clearance of cortisone acetate is not readily available.

    5.5 Mechanism of Action

    The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days. Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10. Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.