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Desonide

Synopsis, Chemistry

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CREAM;TOPICAL - 0.05%, OINTMENT;TOPICAL - 0.05%, GEL;TOPICAL - 0.05% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

CREAM;TOPICAL - 0.05%
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GEL;TOPICAL - 0.05% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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Also known as: 638-94-8, Prednacinolone, Locapred, Desowen, Desonate, Topifug

Molecular Formula

C₂₄H₃₂O₆

Molecular Weight

416.5 g/mol

InChI Key

WBGKWQHBNHJJPZ-LECWWXJVSA-N

FDA UNII

J280872D1O

A nonfluorinated corticosteroid anti-inflammatory agent used topically for DERMATOSES.

Desonide is a Corticosteroid. The mechanism of action of desonide is as a Corticosteroid Hormone Receptor Agonist.

1 2D Structure

Desonide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

2.1.2 InChI

InChI=1S/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1

2.1.3 InChI Key

WBGKWQHBNHJJPZ-LECWWXJVSA-N

2.1.4 Canonical SMILES

CC1(OC2CC3C4CCC5=CC(=O)C=CC5(C4C(CC3(C2(O1)C(=O)CO)C)O)C)C

2.1.5 Isomeric SMILES

C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)CCC5=CC(=O)C=C[C@]35C)O

2.2 Other Identifiers

2.2.1 UNII

J280872D1O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Desocort

2. Desone

3. Desowen

4. Locapred

5. Locatop

6. Prednacinolone

7. Tridsonit

8. Tridesilon

2.3.2 Depositor-Supplied Synonyms

1. 638-94-8

2. Prednacinolone

3. Locapred

4. Desowen

5. Desonate

6. Topifug

7. Desonida

8. Desonidum

9. Tridesilon

10. Apolar

11. Verdeso

12. D-2083

13. Steroderm

14. Sterax

15. Desfluorotriamcinolone Acetonide

16. 16alpha-hydroxyprednisole-16,17-acetonide

17. Tridesonit

18. D2083

19. Desilux

20. 16alpha,17alpha-isopropylidenedioxyprednisolone

21. Chebi:204734

22. 16alpha-hydroxyprednisolone-16alpha,17-acetonide

23. J280872d1o

24. Nsc-759226

25. Hamiltoderm

26. Flusemidon

27. Reticus

28. Zotinar

29. 11beta,21-dihydroxy-16alpha,17-isopropylidenedioxypregna-1,4-diene-3,20-dione

30. 11beta,21-dihydroxy-16alpha,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

31. 11beta,21-dihydroxy-16alpha,17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione

32. Dsstox_cid_26756

33. Dsstox_rid_81880

34. Dsstox_gsid_46756

35. (1s,2s,4r,8s,9s,11s,12s,13r)-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one

36. D 2083

37. Desonidum [inn-latin]

38. Desonida [inn-spanish]

39. Desonide [usan:inn:ban]

40. Cas-638-94-8

41. Desowen (tn)

42. Verdeso (tn)

43. Mfcd00866151

44. 16-alpha-hydroxyprednisole-16,17-acetonide

45. Unii-j280872d1o

46. Ncgc00167983-01

47. Ncgc00274065-01

48. Einecs 211-351-6

49. Desonide (usp/inn)

50. Desonide [usan]

51. Desonide [inn]

52. Desonide [mi]

53. Desonide [vandf]

54. Desonide [mart.]

55. Desonide [usp-rs]

56. Desonide [who-dd]

57. Schembl3631

58. 11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone

59. Desonide [orange Book]

60. Gtpl7066

61. Desonide [usp Impurity]

62. Chembl1201109

63. Desonide [usp Monograph]

64. Dtxsid7046756

65. Hms3715p20

66. 11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone

67. Bcp04201

68. Hy-b0248

69. Pregna-1,4-diene-3,20-dione, 11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11.beta.,16.alpha.)-

70. Tridesilon Component Desonide

71. Zinc4212851

72. Tox21_112603

73. 16alpha-hydroxyprednisolone Acetonide

74. S1701

75. Akos037643323

76. Tox21_112603_1

77. Ccg-221279

78. Db01260

79. Desonide Component Of Tridesilon

80. Nsc 759226

81. (4ar,4bs,5s,6as,6bs,9ar,10as,10bs)-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

82. As-13892

83. Pregna-1,4-diene-3,20-dione, 11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11beta,16alpha)-

84. Budesonide Impurity F [ep Impurity]

85. D5578

86. D03696

87. F20496

88. Ab01274712-01

89. Ab01274712_02

90. 638d948

91. Prednisolone-16,17-acetonide, 16-alpha-hydroxy-

92. Q904011

93. Q-101382

94. Brd-k21528677-001-03-6

95. 16?,17-[1-methylethylidenebis(oxy)]-11?,21-dihydroxypregna-1,4-diene-3,20-dione

96. (11beta,16alpha)-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna -1,4-diene-3,20-dione

97. (1s,2s,4r,8s,9s,11s,12s,13r)-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

98. 16alpha,17-[1-methylethylidenebis(oxy)]-11beta,21-dihydroxypregna-1,4-diene-3,20-dione (desonide)

2.4 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₂O₆
Molecular Weight	416.5 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	416.21988874 g/mol
Monoisotopic Mass	416.21988874 g/mol
Topological Polar Surface Area	93.1 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	873
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 Information

1 of 8
Drug Name	Desonate
PubMed Health	Desonide (On the skin)
Drug Classes	Corticosteroid, Strong
Drug Label	Desonate contains desonide [(pregna-1, 4-diene-3, 20-dione,11, 21-dihydroxy-16, 17-[(1-methylethylidene) bis(oxy)]-,(11,16)]- a synthetic nonfluorinated corticosteroid for topical dermatologic use. Chemically, desonide is C24H32O6. It has the fol...
Active Ingredient	Desonide
Dosage Form	Gel
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Bayer Hlthcare

2 of 8
Drug Name	Desonide
Drug Label	VERDESO Foam is a white to off-white petrolatum-based emulsion aerosol foam containing the active ingredient desonide, a low-potency topical corticosteroid.Chemically, desonide is (11,16)-11,21-dihydroxy-16,17-[(1-methylethylidene)-bis(oxy)]-pregna-1...
Active Ingredient	Desonide
Dosage Form	Lotion; Ointment; Cream
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Fougera Pharms; Perrigo New York; Taro

3 of 8
Drug Name	Desowen
Drug Label	DesOwen Cream 0.05%, Ointment 0.05%, and Lotion 0.05% contain desonide (Pregna-1,4-diene-3,20-dione,11,21-dihydroxy-16,17 [(1methylethylidene) bis(oxy)]-,(11,16)- a synthetic nonfluorinated corticosteroid for topical dermatologic use. The corti...
Active Ingredient	Desonide
Dosage Form	Lotion; Ointment; Cream
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Galderma Labs

4 of 8
Drug Name	Verdeso
PubMed Health	Desonide (On the skin)
Drug Classes	Corticosteroid, Strong
Drug Label	VERDESO Foam is a white to off-white petrolatum-based emulsion aerosol foam containing the active ingredient desonide, a low-potency topical corticosteroid.Chemically, desonide is (11,16)-11,21-dihydroxy-16,17-[(1-methylethylidene)-bis(oxy)]-pregna-1...
Active Ingredient	Desonide
Dosage Form	Aerosol, foam
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Aqua Pharms

5 of 8
Drug Name	Desonate
PubMed Health	Desonide (On the skin)
Drug Classes	Corticosteroid, Strong
Drug Label	Desonate contains desonide [(pregna-1, 4-diene-3, 20-dione,11, 21-dihydroxy-16, 17-[(1-methylethylidene) bis(oxy)]-,(11,16)]- a synthetic nonfluorinated corticosteroid for topical dermatologic use. Chemically, desonide is C24H32O6. It has the fol...
Active Ingredient	Desonide
Dosage Form	Gel
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Bayer Hlthcare

6 of 8
Drug Name	Desonide
Drug Label	VERDESO Foam is a white to off-white petrolatum-based emulsion aerosol foam containing the active ingredient desonide, a low-potency topical corticosteroid.Chemically, desonide is (11,16)-11,21-dihydroxy-16,17-[(1-methylethylidene)-bis(oxy)]-pregna-1...
Active Ingredient	Desonide
Dosage Form	Lotion; Ointment; Cream
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Fougera Pharms; Perrigo New York; Taro

7 of 8
Drug Name	Desowen
Drug Label	DesOwen Cream 0.05%, Ointment 0.05%, and Lotion 0.05% contain desonide (Pregna-1,4-diene-3,20-dione,11,21-dihydroxy-16,17 [(1methylethylidene) bis(oxy)]-,(11,16)- a synthetic nonfluorinated corticosteroid for topical dermatologic use. The corti...
Active Ingredient	Desonide
Dosage Form	Lotion; Ointment; Cream
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Galderma Labs

8 of 8
Drug Name	Verdeso
PubMed Health	Desonide (On the skin)
Drug Classes	Corticosteroid, Strong
Drug Label	VERDESO Foam is a white to off-white petrolatum-based emulsion aerosol foam containing the active ingredient desonide, a low-potency topical corticosteroid.Chemically, desonide is (11,16)-11,21-dihydroxy-16,17-[(1-methylethylidene)-bis(oxy)]-pregna-1...
Active Ingredient	Desonide
Dosage Form	Aerosol, foam
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Aqua Pharms

4.2 Drug Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatose.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Desonide is a synthetic nonfluorinated corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents.

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 Active Moiety

DESONIDE

5.3.2 FDA UNII

J280872D1O

5.3.3 Pharmacological Classes

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

5.4 ATC Code

D07AB08

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AB - Corticosteroids, moderately potent (group ii)

D07AB08 - Desonide

S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BA - Corticosteroids, plain

S01BA11 - Desonide

5.5 Absorption, Distribution and Excretion

Absorption

Topical corticosteroids can be absorbed from normal intact skin, inflammation and/or other disease processes in the skin may increase percutaneous absorption.

5.6 Mechanism of Action

Like other topical corticosteroids, desonide has anti-inflammatory, antipruritic and vasoconstrictive properties. The drug binds to cytosolic glucocorticoid receptors. This complex migrates to the nucleus and binds to genetic elements on the DNA. This activates and represses various genes. 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.

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