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11-Dehydro-17-hydroxycorticosterone Acetate

11-Dehydro-17-hydroxycorticosterone acetate

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11-Dehydro-17-hydroxycorticosterone acetate

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

11-Dehydro-17-hydroxycorticosterone acetate

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 Formula	C₂₃H₃₀O₆
Molecular Weight	402.5 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	402.20423867 g/mol
Monoisotopic Mass	402.20423867 g/mol
Topological Polar Surface Area	97.7 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	827
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
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 Information

1 of 2
Drug Name	Cortisone acetate
PubMed Health	Cortisone Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent, Immune Suppressant
Drug Label	Glucocorticoids 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 Ingredient	Cortisone acetate
Dosage Form	Tablet
Route	Oral
Strength	25mg
Market Status	Prescription
Company	Hikma Pharms

2 of 2
Drug Name	Cortisone acetate
PubMed Health	Cortisone Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent, Immune Suppressant
Drug Label	Glucocorticoids 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 Ingredient	Cortisone acetate
Dosage Form	Tablet
Route	Oral
Strength	25mg
Market Status	Prescription
Company	Hikma 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.