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2D Structure
Also known as: 25122-46-7, Clobetasol 17-propionate, Clobex, Dermovate, Temovate, Embeline
Molecular Formula
C25H32ClFO5
Molecular Weight
467.0  g/mol
InChI Key
CBGUOGMQLZIXBE-XGQKBEPLSA-N
FDA UNII
779619577M

A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
2.1.2 InChI
InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
2.1.3 InChI Key
CBGUOGMQLZIXBE-XGQKBEPLSA-N
2.1.4 Canonical SMILES
CCC(=O)OC1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)C(=O)CCl
2.1.5 Isomeric SMILES
CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)C(=O)CCl
2.2 Other Identifiers
2.2.1 UNII
779619577M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Clobetasol

2. Clobetasol 17 Propionate

3. Clobetasol 17-propionate

4. Clobex

5. Clofenazon

6. Cormax

7. Dermovate

8. Embeline

9. Embeline E

10. Olux

11. Temovate

2.3.2 Depositor-Supplied Synonyms

1. 25122-46-7

2. Clobetasol 17-propionate

3. Clobex

4. Dermovate

5. Temovate

6. Embeline

7. Cormax

8. Olux

9. Gr 2/925

10. Cci 4725

11. Clobestasol Propionate

12. Impoyz

13. Psorex

14. [(8s,9r,10s,11s,13s,14s,16s,17r)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] Propanoate

15. Clobetasol 17-propanoate

16. Clobetasol-17-propionate

17. Mls000028708

18. Cci-4725

19. 21-chloro-9-fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-propionate

20. Embeline E

21. Smr000058745

22. Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (11beta,16beta)-

23. Clobesol

24. Chebi:31414

25. Temovate E

26. Nsc-758634

27. Dsstox_cid_25907

28. Dsstox_rid_81219

29. Dsstox_gsid_45907

30. Olux-e

31. 779619577m

32. Dermoxinale

33. Butavate

34. Dermoval

35. Yugofin

36. 21-chloro-9-fluoro-11beta-hydroxy-16beta-methyl-3,20-dioxopregna-1,4-dien-17-yl Propanoate

37. Olux E

38. Cgp 9555

39. Clobetasol Propionate Gel

40. Einecs 246-634-3

41. Clobetasol Propionate (emollient)

42. Clarelux

43. Ncgc00095078-01

44. Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (11.beta.,16.beta.)-

45. Clobetasol-propionate

46. Cas-25122-46-7

47. Clobex (tn)

48. Cormax (tn)

49. Mfcd00058499

50. Unii-779619577m

51. Impeklo

52. Clobetasol Propionate [usan:usp:jan]

53. Olux (tn)

54. Clobetasol Propionate E

55. Propionic Acid Clobetasol

56. Opera_id_1470

57. Schembl3997

58. 21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione (11beta,16beta)-

59. Cid_32798

60. Mls001076345

61. Amot0927

62. Gtpl7062

63. Ccl 4725

64. Chembl1159650

65. Dtxsid6045907

66. Bdbm39347

67. Cgp9555

68. Clobetasol Propionate [mi]

69. Hms2090a04

70. Hms2230h08

71. Hms3259a10

72. Hms3714m04

73. Clobetasol Propionate (jp17/usp)

74. Clobetasol Propionate [jan]

75. Bcp04125

76. Zinc3977767

77. Clobetasol Propionate [usan]

78. Tox21_111414

79. Am9637

80. Clobetasol Propionate [vandf]

81. S2584

82. Clobetasol Propionate [mart.]

83. Akos015951278

84. Clobetasol Propionate [usp-rs]

85. Clobetasol Propionate [who-dd]

86. Tox21_111414_1

87. Bcp9000539

88. Ccg-220781

89. Clobetasol 17-propionate [mi]

90. Db01013

91. Nc00551

92. Nsc 758634

93. 21-chloro-9-fluoro-11beta-hydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-propionate

94. Ncgc00023373-03

95. Ncgc00023373-04

96. Ac-17990

97. As-12555

98. Clobetasol Propionate, Analytical Standard

99. Cpd000058745

100. Gr-2/925

101. Hy-13600

102. Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11-beta,17-dihydroxy-16-beta-methyl-, 17-propionate

103. Bcp0726000094

104. Clobetasol Propionate [orange Book]

105. Clobetasol Propionate [usp Impurity]

106. Clobetasol Propionate [usp Monograph]

107. D01272

108. D94623

109. Ab00383081-10

110. Ab00383081_11

111. 122c467

112. Clobetasol Propionate 1000 Microg/ml In Methanol

113. Q421637

114. Sr-01000000280

115. Clobetasol Propionate 100 Microg/ml In Acetonitrile

116. Sr-01000000280-4

117. Brd-k10799896-001-10-6

118. Brd-k10799896-001-26-2

119. Clobetasol Propionate 100 Microg/ml In Methanol/water

120. Clobetasol Propionate, European Pharmacopoeia (ep) Reference Standard

121. Clobetasol Propionate, United States Pharmacopeia (usp) Reference Standard

122. Clobetasol For Peak Identification, European Pharmacopoeia (ep) Reference Standard

123. Clobetasol Propionate, Pharmaceutical Secondary Standard; Certified Reference Material

124. (8alpha,11beta,14beta,16alpha,17alpha)-21-chloro-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl Propanoate

125. 21-chloro-9-fluoro-11.beta.,17-dihydroxy-16.beta.-methylpregna-1,4-diene-3,20-dione 17-propionate

126. 21-chloro-9alpha-fluoro-11beta,17alpha-dihydroxy-16beta-methyl-1,4-pregnadiene-3,20-dione 17-propionate

127. Cgp9555 Pound>> Ccl 4725 Pound>>cgp 9555 Pound>> Ccl4725 Pound>>cgp-9555 Pound>> Ccl-4725

128. Xrd

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 467.0 g/mol
Molecular Formula C25H32ClFO5
XLogP33.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass466.1922300 g/mol
Monoisotopic Mass466.1922300 g/mol
Topological Polar Surface Area80.7 Ų
Heavy Atom Count32
Formal Charge0
Complexity929
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 20  
Drug NameClobetasol propionate
Active IngredientClobetasol propionate
Dosage FormLotion; Gel; Shampoo; Ointment; Cream; Spray; Aerosol, foam; Solution
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyWockhardt; Fougera Pharms; Teva Pharms; Paddock; Actavis Mid Atlantic; Perrigo; Taro; Fougera; Tolmar; Perrigo Israel

2 of 20  
Drug NameClobetasol propionate
PubMed HealthClobetasol Propionate (On the skin)
Drug ClassesCorticosteroid, Very Strong
Drug LabelClobetasol propionate cream USP, 0.05% (emollient) contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degre...
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyFougera Pharms; Taro

3 of 20  
Drug NameClobex
Drug LabelCLOBEX (clobetasol propionate) Lotion, 0.05% contains clobetasol propionate, a synthetic fluorinated corticosteroid, for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflamm...
Active IngredientClobetasol propionate
Dosage FormLotion; Shampoo; Spray
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyGalderma Labs

4 of 20  
Drug NameCormax
PubMed HealthClobetasol Propionate (On the skin)
Drug ClassesCorticosteroid, Very Strong
Drug LabelCormax Ointment contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical dermatologic use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree of mineralocorticoid...
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyHi Tech Pharma

5 of 20  
Drug NameEmbeline
Drug LabelClobetasol propionate foam, 0.05% contains clobetasol propionate, USP, a synthetic corticosteroid, for topical dermatologic use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree of mineralocortic...
Active IngredientClobetasol propionate
Dosage FormGel; Ointment; Solution
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyHi Tech Pharma

6 of 20  
Drug NameEmbeline e
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyHi Tech Pharma

7 of 20  
Drug NameOlux
PubMed HealthClobetasol
Drug ClassesCorticosteroid, Very Strong, Corticosteroid, Weak
Drug LabelOLUX-E (clobetasol propionate) Foam, 0.05% is a white to off-white petrolatum-based emulsion aerosol foam containing the active ingredient clobetasol propionate USP, a synthetic corticosteroid for topical dermatologic use. Clobetasol, an analog of pr...
Active IngredientClobetasol propionate
Dosage FormAerosol, foam
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyDelcor Asset

8 of 20  
Drug NameOlux e
PubMed HealthClobetasol
Drug ClassesCorticosteroid, Very Strong, Corticosteroid, Weak
Active IngredientClobetasol propionate
Dosage FormAerosol, foam
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyDelcor Asset

9 of 20  
Drug NameTemovate
PubMed HealthClobetasol
Drug ClassesCorticosteroid, Very Strong, Corticosteroid, Weak
Drug LabelTemovate E (clobetasol propionate) Cream, 0.05% contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree...
Active IngredientClobetasol propionate
Dosage FormOintment; Cream; Gel
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyFougera Pharms

10 of 20  
Drug NameTemovate e
PubMed HealthClobetasol Propionate (On the skin)
Drug ClassesCorticosteroid, Very Strong
Drug LabelTemovate E (clobetasol propionate) Cream, 0.05% contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree...
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyFougera Pharms

11 of 20  
Drug NameClobetasol propionate
Active IngredientClobetasol propionate
Dosage FormLotion; Gel; Shampoo; Ointment; Cream; Spray; Aerosol, foam; Solution
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyWockhardt; Fougera Pharms; Teva Pharms; Paddock; Actavis Mid Atlantic; Perrigo; Taro; Fougera; Tolmar; Perrigo Israel

12 of 20  
Drug NameClobetasol propionate
PubMed HealthClobetasol Propionate (On the skin)
Drug ClassesCorticosteroid, Very Strong
Drug LabelClobetasol propionate cream USP, 0.05% (emollient) contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degre...
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyFougera Pharms; Taro

13 of 20  
Drug NameClobex
Drug LabelCLOBEX (clobetasol propionate) Lotion, 0.05% contains clobetasol propionate, a synthetic fluorinated corticosteroid, for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflamm...
Active IngredientClobetasol propionate
Dosage FormLotion; Shampoo; Spray
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyGalderma Labs

14 of 20  
Drug NameCormax
PubMed HealthClobetasol Propionate (On the skin)
Drug ClassesCorticosteroid, Very Strong
Drug LabelCormax Ointment contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical dermatologic use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree of mineralocorticoid...
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyHi Tech Pharma

15 of 20  
Drug NameEmbeline
Drug LabelClobetasol propionate foam, 0.05% contains clobetasol propionate, USP, a synthetic corticosteroid, for topical dermatologic use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree of mineralocortic...
Active IngredientClobetasol propionate
Dosage FormGel; Ointment; Solution
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyHi Tech Pharma

16 of 20  
Drug NameEmbeline e
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyHi Tech Pharma

17 of 20  
Drug NameOlux
PubMed HealthClobetasol
Drug ClassesCorticosteroid, Very Strong, Corticosteroid, Weak
Drug LabelOLUX-E (clobetasol propionate) Foam, 0.05% is a white to off-white petrolatum-based emulsion aerosol foam containing the active ingredient clobetasol propionate USP, a synthetic corticosteroid for topical dermatologic use. Clobetasol, an analog of pr...
Active IngredientClobetasol propionate
Dosage FormAerosol, foam
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyDelcor Asset

18 of 20  
Drug NameOlux e
PubMed HealthClobetasol
Drug ClassesCorticosteroid, Very Strong, Corticosteroid, Weak
Active IngredientClobetasol propionate
Dosage FormAerosol, foam
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyDelcor Asset

19 of 20  
Drug NameTemovate
PubMed HealthClobetasol
Drug ClassesCorticosteroid, Very Strong, Corticosteroid, Weak
Drug LabelTemovate E (clobetasol propionate) Cream, 0.05% contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree...
Active IngredientClobetasol propionate
Dosage FormOintment; Cream; Gel
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyFougera Pharms

20 of 20  
Drug NameTemovate e
PubMed HealthClobetasol Propionate (On the skin)
Drug ClassesCorticosteroid, Very Strong
Drug LabelTemovate E (clobetasol propionate) Cream, 0.05% contains the active compound clobetasol propionate, a synthetic corticosteroid, for topical use. Clobetasol, an analog of prednisolone, has a high degree of glucocorticoid activity and a slight degree...
Active IngredientClobetasol propionate
Dosage FormCream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyFougera Pharms

4.2 Drug Indication

Clobetasol propionate is indicated to treat moderate to severe plaque psoriasis as well as inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Clobetasol propionate is generally applied twice daily so the duration of action is long. 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.)


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 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 Absorption, Distribution and Excretion

Absorption

Twice daily application of clobetasol foam leads to a Cmax of 5936pg/mL with a Tmax of 5 hours. Clobetasol cream showed an increase in clobetasol concentrations from 50.796.0pg/mL to 56.3104.7pg/mL.


Route of Elimination

Corticosteroids are eliminated predominantly in the urine.


Volume of Distribution

Data regarding the volume of distribution of clobetasole propionate are not readily available.


Clearance

Data regarding the clearance of clobetasol propionate are not readily available.


5.5 Metabolism/Metabolites

The metabolism of clobetasol propionate is not well studied but it does induce metabolic enzymes, even when delivered topically. The metabolism of clobetasol propionate is predicted to follow similar metabolic pathways to other corticosteroids including the addition of oxygen, hydrogen, glucuronides, and sulfates to form water soluble metabolites.


5.6 Biological Half-Life

Data regarding the half life of clobetasol propionate are not readily available.


5.7 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.