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    Chemistry

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    Also known as: Hydrocortisone 17-butyrate, Cortisol 17-butyrate, Hydrocortisone-17-butyrate, 13609-67-1, Locoid, Hydrocortisone-17alpha-butyrate
    Molecular Formula
    C25H36O6
    Molecular Weight
    432.5  g/mol
    InChI Key
    BMCQMVFGOVHVNG-TUFAYURCSA-N
    FDA UNII
    05RMF7YPWN
    Hydrocortisone Butyrate
    Hydrocortisone Butyrate is the butyrate salt form of hydrocortisone, a synthetic glucocorticoid receptor agonist with antiinflammatory, antipruritic and vasoconstrictive effects. Binding and activation of the glucocorticoid receptor results in the activation of lipocortin that in turn inhibits cytosolic phospholipase A2. Lack of phospholipase A2 prevents the release of arachidonic acid, precursor for inflammatory mediator prostaglandins and leukotrienes, from the cell membrane. Secondly, mitogen-activated protein kinase (MAPK) phosphatase 1 is induced, thereby leading to dephosphorylation and inactivation of Jun N-terminal kinase directly inhibiting c-Jun mediated transcription. Finally, transcriptional activity of nuclear factor (NF)-kappa-B is blocked, thereby inhibits the transcription of cyclooxygenase 2, which is essential for prostaglandin production.
    1 2D Structure

    Hydrocortisone Butyrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] butanoate
    2.1.2 InChI
    InChI=1S/C25H36O6/c1-4-5-21(30)31-25(20(29)14-26)11-9-18-17-7-6-15-12-16(27)8-10-23(15,2)22(17)19(28)13-24(18,25)3/h12,17-19,22,26,28H,4-11,13-14H2,1-3H3/t17-,18-,19-,22+,23-,24-,25-/m0/s1
    2.1.3 InChI Key
    BMCQMVFGOVHVNG-TUFAYURCSA-N
    2.1.4 Canonical SMILES
    CCCC(=O)OC1(CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C)C(=O)CO
    2.1.5 Isomeric SMILES
    CCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C)C(=O)CO
    2.2 Other Identifiers
    2.2.1 UNII
    05RMF7YPWN
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cortisol 17-butyrate

    2. Hydrocortisone 17-butyrate

    3. Hydrocortisone-17-butyrate

    4. Locoid

    2.3.2 Depositor-Supplied Synonyms

    1. Hydrocortisone 17-butyrate

    2. Cortisol 17-butyrate

    3. Hydrocortisone-17-butyrate

    4. 13609-67-1

    5. Locoid

    6. Hydrocortisone-17alpha-butyrate

    7. 17-o-butyrylcortisol

    8. 11beta,17,21-trihydroxypregn-4-ene-3,20-dione 17-butyrate

    9. H-17-b

    10. Chebi:31674

    11. 05rmf7ypwn

    12. Mls000028716

    13. Mls001076086

    14. Laticort

    15. Nsc-758433

    16. Alfason

    17. Hycortate

    18. Lacoidon

    19. Smr000058859

    20. Bucort

    21. Lacoid

    22. Dsstox_cid_25896

    23. Dsstox_rid_81208

    24. Dsstox_gsid_45896

    25. 11beta,21-dihydroxy-3,20-dioxopregn-4-en-17-yl Butanoate

    26. 11beta,21-dihydroxy-17alpha-butyryloxy-4-pregnene-3,20-dione

    27. Hb(sub 17)

    28. Cas-13609-67-1

    29. Cortisol, 17-butyrate

    30. H.17b

    31. [(8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Butanoate

    32. Einecs 237-093-4

    33. Unii-05rmf7ypwn

    34. Ncgc00095037-01

    35. Locoid (tn)

    36. Hydrocortisone-butyrate

    37. Opera_id_188

    38. Hydrocortisone Butyrate [usan:usp:ban:jan]

    39. Butyric Acid Hydrocortisone

    40. Epitope Id:119710

    41. 11-beta,17-alpha,21-trihydroxy-4-pregnene-3,20-dione 17-alpha-butyrate

    42. Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11-beta)-

    43. Schembl4695

    44. Chembl1683

    45. Mls002207122

    46. Dtxsid4045896

    47. Bdbm323672

    48. Hms2231b16

    49. Bcp11925

    50. Hy-b0983

    51. Zinc3977794

    52. Tox21_111397

    53. Ac-492

    54. Hydrocortisone Butyrate (jp17/usp)

    55. Hydrocortisone Butyrate [jan]

    56. S6590

    57. Hydrocortisone Butyrate [usan]

    58. Akos015895443

    59. Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11.beta.)-

    60. Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11beta)-

    61. Tox21_111397_1

    62. Cs-4474

    63. Db14540

    64. Hydrocortisone Butyrate [mart.]

    65. Hydrocortisone Butyrate [vandf]

    66. Nsc 758433

    67. Hydrocortisone Butyrate [usp-rs]

    68. Hydrocortisone Butyrate [who-dd]

    69. Hydrocortisone 17-butyrate [mi]

    70. Ncgc00274077-01

    71. Us10188667, Example 00013

    72. Us10188667, Example 00024

    73. (1s,10s,11s,15s,17s,2r,14r)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-ox Otetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-6-en-14-yl Butanoate

    74. H1506

    75. Hydrocortisone Butyrate [orange Book]

    76. D01619

    77. Hydrocortisone Butyrate [usp Monograph]

    78. 609h671

    79. A807026

    80. Q5954743

    81. W-108252

    82. Hydrocortisone 17-butyrate 100 Microg/ml In Methanol

    83. Hydrocortisone Butyrate (hydrocortisone 17-butyrate)

    84. 11.beta.,17,21-trihydroxypregn-4-ene-3,20-dione 17-butyrate

    85. Hydrocortisone Butyrate, United States Pharmacopeia (usp) Reference Standard

    86. (8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl Butanoate

    87. [(8s,9s,10r,11s,13s,14s,17r)-10,13-dimethyl-11-oxidanyl-17-(2-oxidanylethanoyl)-3-oxidanylidene-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Butanoate

    88. Butanoic Acid [(8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-17-(2-hydroxy-1-oxoethyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Ester

    2.3.3 Other Synonyms

    1. Hydrocortisone Butyrate Propionate

    2. Hydrocortisone Buteprate

    3.  Hydrocortisone Probutate

    4. Pandel

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 432.5 g/mol
    Molecular Formula C25H36O6
    XLogP33.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass432.25118886 g/mol
    Monoisotopic Mass432.25118886 g/mol
    Topological Polar Surface Area101 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity817
    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 3  
    Drug NameLOCOID
    Active IngredientHYDROCORTISONE BUTYRATE
    CompanyPRECISION DERMAT (Application Number: N018514); PRECISION DERMAT (Application Number: N018652); PRECISION DERMAT (Application Number: N019116); PRECISION DERMAT (Application Number: N022076. Patents: 7378405, 7981877)

    2 of 3  
    Drug NameHYDROCORTISONE BUTYRATE
    Active IngredientHYDROCORTISONE BUTYRATE
    CompanyACTAVIS MID ATLANTIC (Application Number: A205134); GLENMARK GENERICS (Application Number: A202145); TARO PHARM INDS (Application Number: A076364); TARO PHARM INDS (Application Number: A076654); TARO (Application Number: A076842); TELIGENT PHARMA INC (Application Number: A209556)

    3 of 3  
    Drug NameLOCOID LIPOCREAM
    Active IngredientHYDROCORTISONE BUTYRATE
    CompanyPRECISION DERMAT (Application Number: N020769)

    4.2 Drug Indication

    For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). It is also used to treat many immune and allergic disorders, such as arthritis, lupus, severe psoriasis, severe asthma, ulcerative colitis, and Crohn's disease.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Hydrocortisone is the most important human glucocorticoid. It is essential for life and regulates or supports a variety of important cardiovascular, metabolic, immunologic and homeostatic functions. Topical hydrocortisone is used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger a variety of important cardiovascular, metabolic, immunologic and homeostatic effects. Glucocorticoids are distinguished from mineralocorticoids and sex steroids by having different receptors, target cells, and effects. Technically, the term corticosteroid refers to both glucocorticoids and mineralocorticoids, but is often used as a synonym for glucocorticoid. Glucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.

    5.2 MeSH Pharmacological Classification

    Dermatologic Agents

    Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.4 ATC Code

    D - Dermatologicals

    D07 - Corticosteroids, dermatological preparations

    D07A - Corticosteroids, plain

    D07AB - Corticosteroids, moderately potent (group ii)

    D07AB02 - Hydrocortisone butyrate

    5.5 Absorption, Distribution and Excretion

    Absorption

    Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.

    Route of Elimination

    Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.

    5.6 Metabolism/Metabolites

    Primarily hepatic via CYP3A4

    5.7 Biological Half-Life

    6-8 hours

    5.8 Mechanism of Action

    Hydrocortisone 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. The cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In other 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.

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    DOSAGE - CREAM;TOPICAL - 0.1%

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