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    Trilostane

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    MARKET PLACE

    PharmaCompass
    $ API Ref.Price (USD/KG) : 3,923Xls

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    2D Structure
    Also known as: 13647-35-3, Modrenal, Vetoryl, Desopan, Modrastane, Trilostanum
    Molecular Formula
    C20H27NO3
    Molecular Weight
    329.4  g/mol
    InChI Key
    KVJXBPDAXMEYOA-CXANFOAXSA-N
    FDA UNII
    L0FPV48Q5R
    Trilostane is a synthetic derivative of androstane with adrenocortical suppressive properties. Trilostane reversibly inhibits 3 beta-hydroxysteroid dehydrogenase delta 5-4 isomerase in the adrenal cortex, resulting in the decreased synthesis of mineralocorticoids and glucocorticoids and the decreased conversion of pregnenolone to progesterone. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile
    2.1.2 InChI
    InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
    2.1.3 InChI Key
    KVJXBPDAXMEYOA-CXANFOAXSA-N
    2.1.4 Canonical SMILES
    CC12CCC3C(C1CCC2O)CCC45C3(CC(=C(C4O5)O)C#N)C
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@]45[C@@]3(CC(=C([C@H]4O5)O)C#N)C
    2.2 Other Identifiers
    2.2.1 UNII
    L0FPV48Q5R
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4alpha,5-epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile

    2. Modrenal

    3. Win 24,540

    2.3.2 Depositor-Supplied Synonyms

    1. 13647-35-3

    2. Modrenal

    3. Vetoryl

    4. Desopan

    5. Modrastane

    6. Trilostanum

    7. Trilostano

    8. Win-24540

    9. Win 24,540

    10. Chebi:32260

    11. L0fpv48q5r

    12. Win 24540

    13. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4alpha,5alpha,17beta)-

    14. Nsc-758904

    15. Dsstox_cid_3706

    16. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4a,5a,17b)-

    17. Dsstox_rid_77157

    18. Dsstox_gsid_23706

    19. (1ar,4ar,4bs,6as,7s,9as,9bs,11as)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile

    20. (1s,2r,6r,8s,11s,12s,15s,16s)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

    21. Modrenal (tn)

    22. (1ar,4ar,4bs,6as,7s,9as,9bs,11as)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile.

    23. (1s,2r,6r,8s,11s,12s,15s,16s)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile

    24. Desopan (tn)

    25. Cas-13647-35-3

    26. Trilostane (jan/usan)

    27. Trilostanum [inn-latin]

    28. Trilostano [inn-spanish]

    29. Unii-l0fpv48q5r

    30. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4.alpha.,5.alpha.,17.beta.)-

    31. Trilostane [usan:inn:ban:jan]

    32. Ncgc00274061-01

    33. Einecs 237-133-0

    34. Mfcd00199295

    35. Win 24450

    36. Trilostane [mi]

    37. Trilostane [inn]

    38. Trilostane [jan]

    39. Trilostane [usan]

    40. Trilostane [vandf]

    41. (4alpha,5alpha,17beta)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile

    42. Schembl7517

    43. Trilostane [mart.]

    44. Trilostane [who-dd]

    45. Gtpl6850

    46. Trilostane [green Book]

    47. Chembl1200907

    48. Dtxsid9023706

    49. Trilostane [orange Book]

    50. Trilostane, >=98% (hplc)

    51. 4.alpha.,5-epoxy-3,17.beta.-dihydroxy-5.alpha.-androst-2-ene-2-carbonitrile

    52. Hms3884a15

    53. Bcp04132

    54. Tox21_112454

    55. Tox21_302406

    56. 4-alpha,5-epoxy-3,17-dihydroxy-5-alpha-androst-2-ene-2-carbonitrile

    57. Ac-927

    58. Bdbm50247882

    59. S1404

    60. 3,17beta-dihydroxy-4alpha,5-epoxy-5alpha-androst-2-ene-2-carbonitrile

    61. 4alpha,5-epoxy-3,17beta-dihydroxy-5alpha-androst-2-ene-2-carbonitrile

    62. Akos015964043

    63. Akos032947221

    64. Tox21_112454_1

    65. Zinc100038546

    66. Ccg-267803

    67. Cs-1707

    68. Db01108

    69. Ks-1414

    70. Nsc 758904

    71. (2-alpha,4-alpha,5-alpha,17-beta)-4,5-epoxy-17-hydroxy-3-oxoandrostane-2-carbonitrile

    72. 4-alpha-5-epoxy-17-beta-hydroxy-3-oxo-5-alpha-androstane-2-alpha-carbonitrile

    73. Androstane-2-carbonitrile, 4,5-epoxy-17-hydroxy-3-oxo-, (2-alpha,4-alpha,5-alpha,17-beta)-

    74. Ncgc00255201-01

    75. Hy-14281

    76. Bcp0726000098

    77. D01180

    78. Ab01274788-01

    79. Ab01274788_02

    80. 647t353

    81. A886681

    82. Q907313

    83. Q-201884

    84. Z1563146079

    85. Trilostane; 13647-35-3; Vetoryl; Modrenal; Modrastane

    86. (4a,5a,17b)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile

    87. 5-alpha-androstane-2-alpha-carbonitrile, 4-alpha,5-epoxy-17-beta-hydroxy-3-oxo-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 329.4 g/mol
    Molecular Formula C20H27NO3
    XLogP32.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count0
    Exact Mass329.19909372 g/mol
    Monoisotopic Mass329.19909372 g/mol
    Topological Polar Surface Area76.8 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity692
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    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

    Used in the treatment of Cushing's syndrome. It is normally used in short-term treatment until permanent therapy is possible.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Trilostane blocks an enzyme involved in the production of several steroids including cortisol. Inhibiting this enzyme inhibits the production of cortisol. In Cushing's syndrome, the adrenal gland overproduces steroids. Although steroids are important for various functions of the body, too much can cause problems. Trilostane reduces the amount of steroids produced by the adrenal gland. This product was withdrawn from the U.S. market in April 1994.

    5.2 MeSH Pharmacological Classification

    Abortifacient Agents, Steroidal

    Steroidal compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Steroidal.)

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    5.3 ATC Code

    H - Systemic hormonal preparations, excl. sex hormones and insulins

    H02 - Corticosteroids for systemic use

    H02C - Antiadrenal preparations

    H02CA - Anticorticosteroids

    H02CA01 - Trilostane

    5.4 Metabolism/Metabolites

    Hepatic.

    5.5 Biological Half-Life

    8 hours.

    5.6 Mechanism of Action

    Trilostane produces suppression of the adrenal cortex by inhibiting enzymatic conversion of steroids by 3-beta-hydroxysteroid dehydrogenase/delta 5,4 ketosteroid isomerase, thus blocking synthesis of adrenal steroids.