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Chemistry

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Also known as: 382-67-2, Desoxymethasone, Topicort, Desoximetasona, Desoximetasonum, Topicort lp
Molecular Formula
C22H29FO4
Molecular Weight
376.5  g/mol
InChI Key
VWVSBHGCDBMOOT-IIEHVVJPSA-N
FDA UNII
4E07GXB7AU

Desoximetasone
A topical anti-inflammatory glucocorticoid used in DERMATOSES, skin allergies, PSORIASIS, etc.
Desoximetasone is a Corticosteroid. The mechanism of action of desoximetasone is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

Desoximetasone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
2.1.3 InChI Key
VWVSBHGCDBMOOT-IIEHVVJPSA-N
2.1.4 Canonical SMILES
CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1C(=O)CO)C)O)F)C
2.1.5 Isomeric SMILES
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@H]1C(=O)CO)C)O)F)C
2.2 Other Identifiers
2.2.1 UNII
4E07GXB7AU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17 Desoxymethasone

2. 17-desoxymethasone

3. A 41304

4. A-41304

5. A41304

6. Deoxydexamethasone

7. Desoxi

8. Desoxymethasone

9. Flubason

10. Ibaril

11. Stiedex

12. Topicort

13. Topicorte

14. Topisolon

2.3.2 Depositor-Supplied Synonyms

1. 382-67-2

2. Desoxymethasone

3. Topicort

4. Desoximetasona

5. Desoximetasonum

6. Topicort Lp

7. Desoxymetasone

8. Hoe-304

9. Hoe 304

10. A-41-304

11. Deoxymethasone

12. 9-fluoro-11beta,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione

13. R-2113

14. (8s,9r,10s,11s,13s,14s,16r,17s)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6h-cyclopenta[a]phenanthren-3-one

15. Chebi:691037

16. Dexamethasone Impurity F

17. R 2113

18. 4e07gxb7au

19. Esperson

20. Mls000028654

21. 17-deoxymethansone

22. 17-desoximethasone

23. A-41304

24. 9alpha-fluoro-16alpha-methyl-delta(1)-corticosterone

25. Nsc-759189

26. (8s,9r,10s,11s,13s,14s,16r,17s)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-3-one

27. 140218-14-0

28. Ncgc00023648-03

29. Flubason

30. J83.644c

31. Smr000058856

32. Stiedex

33. Ibaril

34. (11beta,16alpha)-9-fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione

35. Dsstox_cid_25647

36. Dsstox_rid_81025

37. Dsstox_gsid_45647

38. Desossimetasone

39. A 41304

40. Topicort (tn)

41. Cas-382-67-2

42. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16-methyl-, Labeled With Tritium, (11beta,16alpha)-

43. Desossimetasone [dcit]

44. A 41-304

45. Desoximetasone (usp/inn)

46. Unii-4e07gxb7au

47. Desoximetasonum [inn-latin]

48. Desoximetasona [inn-spanish]

49. Einecs 206-845-3

50. Desoximetasone [usan:usp:inn:ban]

51. Brn 2228097

52. Opera_id_52

53. Desoximetasone [mi]

54. Schembl4214

55. Chembl1766

56. Desoximetasone [inn]

57. Desoximetasone [jan]

58. Desoximetasone [usan]

59. Mls001076073

60. Mls001424230

61. Desoximetasone [vandf]

62. Desoximetasone [mart.]

63. Gtpl7067

64. Desoximetasone [usp-rs]

65. Desoximetasone [who-dd]

66. Dtxsid3045647

67. 9-fluoro-11.beta.,21-dihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dione

68. Hms2052c15

69. Hms2236h07

70. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16-methyl-, (11.beta.,16.alpha.)-

71. Zinc4212854

72. Desoximetasone [orange Book]

73. Tox21_110889

74. Bdbm50103622

75. Desoximetasone [usp Impurity]

76. Mfcd00083301

77. S5685

78. Desoximetasone [usp Monograph]

79. 9-fluoro-11-beta,21-dihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione

80. Akos030254657

81. Tox21_110889_1

82. Ccg-101120

83. Db00547

84. Nc00370

85. Nsc 759189

86. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16-methyl-, (11beta,16alpha)-

87. Ncgc00023648-04

88. As-15787

89. Hy-17570

90. D5515

91. Dexamethasone Impurity F [ep Impurity]

92. D03697

93. T72402

94. 382d672

95. Q385370

96. Q-200938

97. 9alpha-fluoro-11beta,21-dihydroxy-16alpha-methyl-1.4-pregnadiene-3,20-dione

98. (1r,2s,10s,11s,13r,14s,15s,17s)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

2.4 Create Date
2005-06-29
3 Chemical and Physical Properties
Molecular Weight 376.5 g/mol
Molecular Formula C22H29FO4
XLogP32.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass376.20498756 g/mol
Monoisotopic Mass376.20498756 g/mol
Topological Polar Surface Area74.6 Ų
Heavy Atom Count27
Formal Charge0
Complexity757
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 Information
1 of 4  
Drug NameDesoximetasone
Drug LabelTopicort (desoximetasone cream USP) 0.05%, Topicort (desoximetasone cream USP) 0.25%, and Topicort (desoximetasone gel USP) 0.05% contain the active synthetic corticosteroid desoximetasone. The topical corticosteroids constitute a class of prim...
Active IngredientDesoximetasone
Dosage FormGel; Ointment; Cream
RouteTopical
Strength0.05%; 0.25%
Market StatusPrescription
CompanyGlenmark Generics; Fougera Pharms; Versapharm; Perrigo New York

2 of 4  
Drug NameTopicort
PubMed HealthDesoximetasone (On the skin)
Drug ClassesAnti-Inflammatory, Corticosteroid, Strong, Dermatological Agent
Drug LabelTopicort (desoximetasone cream USP) 0.05%, Topicort (desoximetasone cream USP) 0.25%, and Topicort (desoximetasone gel USP) 0.05% contain the active synthetic corticosteroid desoximetasone. The topical corticosteroids constitute a class of prim...
Active IngredientDesoximetasone
Dosage FormOintment; Cream; Spray; Gel
RouteTopical
Strength0.05%; 0.25%
Market StatusPrescription
CompanyTaro; Taro Pharms North

3 of 4  
Drug NameDesoximetasone
Drug LabelTopicort (desoximetasone cream USP) 0.05%, Topicort (desoximetasone cream USP) 0.25%, and Topicort (desoximetasone gel USP) 0.05% contain the active synthetic corticosteroid desoximetasone. The topical corticosteroids constitute a class of prim...
Active IngredientDesoximetasone
Dosage FormGel; Ointment; Cream
RouteTopical
Strength0.05%; 0.25%
Market StatusPrescription
CompanyGlenmark Generics; Fougera Pharms; Versapharm; Perrigo New York

4 of 4  
Drug NameTopicort
PubMed HealthDesoximetasone (On the skin)
Drug ClassesAnti-Inflammatory, Corticosteroid, Strong, Dermatological Agent
Drug LabelTopicort (desoximetasone cream USP) 0.05%, Topicort (desoximetasone cream USP) 0.25%, and Topicort (desoximetasone gel USP) 0.05% contain the active synthetic corticosteroid desoximetasone. The topical corticosteroids constitute a class of prim...
Active IngredientDesoximetasone
Dosage FormOintment; Cream; Spray; Gel
RouteTopical
Strength0.05%; 0.25%
Market StatusPrescription
CompanyTaro; Taro Pharms North

4.2 Drug Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Like other topical corticosteroids, desoximetasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Desoximetasone is a potent topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


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
DESOXIMETASONE
5.3.2 FDA UNII
4E07GXB7AU
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC03 - Desoximetasone


D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07X - Corticosteroids, other combinations

D07XC - Corticosteroids, potent, other combinations

D07XC02 - Desoximetasone


5.5 Absorption, Distribution and Excretion

Absorption

Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.


Route of Elimination

Corticosteroids are bound to plasma proteins in varying degrees, are metabolized primarily in the liver and excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.Pharmacokinetic studies in men with Desoximetasone Cream USP, 0.25% with tagged desoximetasone showed a total of 5.2% 2.9% excretion in urine (4.1% 2.3%) and feces (1.1% 0.6%)


5.6 Metabolism/Metabolites

Metabolized, primarily in the liver, and then excreted by the kidneys.


5.7 Biological Half-Life

The half-life of the material was 15 ± 2 hours (for urine) and 17 ± 2 hours (for feces) between the third and fifth trial day.


5.8 Mechanism of Action

The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. This is achieved first by the drug binding to the glucocorticoid receptors which then translocates into the nucleus and binds to DNA causing various activations and repressions of genes. 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.


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09-Mar-2021
23-Oct-2024
KGS
overview

Average Price (USD/KGS)

6.6k

Number of Transactions

11 - 50

Total Quantity (KGS)

148.5

Total Value (USD)

9,86,079.2

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions
INDONESIA42.974,650.111 - 50
KOREA,REPUBLIC OF95.007,371.2<10
INDIA1.5012,594.5<10
GERMANY4.0010,355.5<10
THAILAND5.005,138.6<10

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