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    Medrysone

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: 2668-66-8, Hydroxymesterone, Medrifar, Medrocort, Medritonic, Visudrisone
    Molecular Formula
    C22H32O3
    Molecular Weight
    344.5  g/mol
    InChI Key
    GZENKSODFLBBHQ-ILSZZQPISA-N
    FDA UNII
    D2UFC189XF
    Medrysone is a topical, synthetic glucocorticoid with metabolic, anti-inflammatory and anti-allergic properties. Medrysone exerts its effect by interacting with specific intracellular glucocorticoid receptors and subsequently binds to DNA to modify gene expression. This results in an induction of the synthesis of certain anti-inflammatory proteins while inhibiting the synthesis of certain inflammatory mediators. Consequently, an overall reduction in chronic inflammation and autoimmune reactions is accomplished.
    Medrysone is a Corticosteroid. The mechanism of action of medrysone is as a Corticosteroid Hormone Receptor Agonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6S,8S,9S,10R,11S,13S,14S,17S)-17-acetyl-11-hydroxy-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
    2.1.2 InChI
    InChI=1S/C22H32O3/c1-12-9-15-17-6-5-16(13(2)23)22(17,4)11-19(25)20(15)21(3)8-7-14(24)10-18(12)21/h10,12,15-17,19-20,25H,5-9,11H2,1-4H3/t12-,15-,16+,17-,19-,20+,21-,22+/m0/s1
    2.1.3 InChI Key
    GZENKSODFLBBHQ-ILSZZQPISA-N
    2.1.4 Canonical SMILES
    CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)CC4)C)O)C)C(=O)C
    2.1.5 Isomeric SMILES
    C[C@H]1C[C@H]2[C@@H]3CC[C@@H]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)CC4)C)O)C)C(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    D2UFC189XF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 11-hydroxy-6-methylprogesterone

    2. Hms Liquifilm

    3. Hms Suspension

    2.3.2 Depositor-Supplied Synonyms

    1. 2668-66-8

    2. Hydroxymesterone

    3. Medrifar

    4. Medrocort

    5. Medritonic

    6. Visudrisone

    7. Hms Liquifilm

    8. 6alpha-methyl-11beta-hydroxyprogesterone

    9. U-8471

    10. Nsc-63278

    11. Medrysone (usan)

    12. 11beta-hydroxy-6alpha-methylpregn-4-ene-3,20-dione

    13. Gsh 1043

    14. (6s,8s,9s,10r,11s,13s,14s,17s)-17-acetyl-11-hydroxy-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

    15. D2ufc189xf

    16. Mls000028714

    17. Chebi:34829

    18. U 8471

    19. 11.beta.-hydroxy-6.alpha.-methylpregn-4-ene-3,20-dione

    20. Smr000058693

    21. Medrysone [usan]

    22. Dsstox_cid_25371

    23. Dsstox_rid_80833

    24. Dsstox_gsid_45371

    25. Medriabioptal

    26. Medrysonum

    27. Sedesterol

    28. Spectramedryn

    29. Medrisona

    30. Medrisone

    31. Medriusar

    32. Medroftal

    33. Medrisone [dcit]

    34. Medrysonum [inn-latin]

    35. Medrisona [inn-spanish]

    36. Unii-d2ufc189xf

    37. Medrysone [usan:usp:inn]

    38. Prestwick_89

    39. Ncgc00016616-01

    40. Cas-2668-66-8

    41. Einecs 220-208-7

    42. Nsc 63278

    43. 11beta-hydroxy-6alpha-methylprogesterone

    44. Cpd000058693

    45. Medrysone [inn]

    46. Opera_id_635

    47. Medrysone [mi]

    48. 6-alpha-methyl-11-beta-hydroxyprogesterone

    49. Prestwick0_000743

    50. Prestwick1_000743

    51. Prestwick2_000743

    52. Prestwick3_000743

    53. Medrysone [vandf]

    54. Progesterone, 11beta-hydroxy-6alpha-methyl-

    55. 11.beta.-hydroxy-6.alpha.-methylprogesterone

    56. 6.alpha.-methyl-11.beta.-hydroxyprogesterone

    57. Medrysone [mart.]

    58. Hms (tn)

    59. Medrysone [who-dd]

    60. Schembl4493

    61. Bspbio_000726

    62. Mls001076155

    63. Mls002207230

    64. Mls002222162

    65. Spbio_002665

    66. Bpbio1_000800

    67. Gtpl7086

    68. Medrysone [orange Book]

    69. 11-beta-hydroxy-6-alpha-methylpregn-4-ene-3,20-dione

    70. Chembl1201173

    71. Dtxsid6045371

    72. 6-methyl-11-hydroxyprogesterone

    73. Bcbcmap01_000088

    74. 6a-methyl-11b-hydroxyprogesterone

    75. Hms1570e08

    76. Hms2097e08

    77. Hms2232f13

    78. Hms3259a22

    79. Hms3714e08

    80. Caa66866

    81. Hy-b1076

    82. Nsc63278

    83. Zinc3977945

    84. Tox21_110526

    85. Akos024285179

    86. Pregn-4-ene-3,20-dione, 11-hydroxy-6-methyl-, (6.alpha.,11.beta.)-

    87. Tox21_110526_1

    88. Ccg-220743

    89. Cs-4632

    90. Db00253

    91. Nc00599

    92. Smp1_000061

    93. 6+/--methyl-11(2)-hydroxyprogesterone

    94. Ncgc00179460-01

    95. Ncgc00179460-03

    96. D02289

    97. 668m668

    98. Progesterone, 11.beta.-hydroxy-6.alpha.-methyl-

    99. Sr-01000721900

    100. Q6807292

    101. Sr-01000721900-3

    102. Brd-k56515112-001-03-4

    103. Brd-k56515112-001-21-6

    104. Pregn-4-ene-3, 11.beta.-hydroxy-6.alpha.-methyl-

    105. Wln: L E5 B666 Ov Mutj A1 Cq E1 Fv1 L1

    106. Pregn-4-ene-3,20-dione, 11beta-hydroxy-6alpha-methyl-

    107. Pregn-4-ene-3,20-dione, 11-beta-hydroxy-6-alpha-methyl-

    108. Medrysone, United States Pharmacopeia (usp) Reference Standard

    109. Pregn-4-ene-3, 11-hydroxy-6-methyl-, (6.alpha.,11.beta.)-

    110. Pregn-4-ene-3,20-dione, 11-hydroxy-6-methyl-, (6alpha,11beta)-

    111. (1s,2r,8s,10s,11s,14s,15s,17s)-14-acetyl-17-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

    112. (6s,10r,11s,13s,17s)-17-acetyl-11-hydroxy-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 344.5 g/mol
    Molecular Formula C22H32O3
    XLogP32.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass344.23514488 g/mol
    Monoisotopic Mass344.23514488 g/mol
    Topological Polar Surface Area54.4 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity650
    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

    For the treatment of allergic conjunctivitis, vernal conjunctivitis, episcleritis, and epinephrine sensitivity.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Medrysone is a topical anti-inflammatory corticoidsteroids for ophthalmic use. In patients with increased intraocular pressure and in those susceptible to a rise in intraocular pressure, there is less effect on pressure with medrysone than with dexamethasone or betamethasone. Corticoidsteroids inhibit the edema, fibrin deposition, capillary dilation, and phagocytic migration of the acute inflammatory response, as well as capillary proliferation, deposition of collagen, and scar formation.

    5.2 MeSH Pharmacological Classification

    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 FDA Pharmacological Classification
    5.3.1 Active Moiety
    MEDRYSONE
    5.3.2 FDA UNII
    D2UFC189XF
    5.3.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
    5.4 ATC Code

    S - Sensory organs

    S01 - Ophthalmologicals

    S01B - Antiinflammatory agents

    S01BA - Corticosteroids, plain

    S01BA08 - Medrysone

    5.5 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following oral administration.

    5.6 Mechanism of Action

    There is no generally accepted explanation for the mechanism of action of ocular corticosteroids. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Initially, the drug binds to the glucocorticoid receptor in the cytosol. This migrates to the nucleus and binds to genetic elements which cause activation and repression of the involved genes in the inflammatory pathway.