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Prestwick3_000743

Prestwick3_000743

Synopsis, Chemistry

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1 Dossiers, 1 FDA Orange Book

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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

Prestwick3_000743

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 Formula	C₂₂H₃₂O₃
Molecular Weight	344.5 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	344.23514488 g/mol
Monoisotopic Mass	344.23514488 g/mol
Topological Polar Surface Area	54.4 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	650
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.