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Also known as: Hydrocortisone 17-butyrate, Cortisol 17-butyrate, Hydrocortisone-17-butyrate, 13609-67-1, Locoid, Hydrocortisone-17alpha-butyrate
Molecular Formula
C25H36O6
Molecular Weight
432.5  g/mol
InChI Key
BMCQMVFGOVHVNG-TUFAYURCSA-N
FDA UNII
05RMF7YPWN

Hydrocortisone Butyrate
Hydrocortisone Butyrate is the butyrate salt form of hydrocortisone, a synthetic glucocorticoid receptor agonist with antiinflammatory, antipruritic and vasoconstrictive effects. Binding and activation of the glucocorticoid receptor results in the activation of lipocortin that in turn inhibits cytosolic phospholipase A2. Lack of phospholipase A2 prevents the release of arachidonic acid, precursor for inflammatory mediator prostaglandins and leukotrienes, from the cell membrane. Secondly, mitogen-activated protein kinase (MAPK) phosphatase 1 is induced, thereby leading to dephosphorylation and inactivation of Jun N-terminal kinase directly inhibiting c-Jun mediated transcription. Finally, transcriptional activity of nuclear factor (NF)-kappa-B is blocked, thereby inhibits the transcription of cyclooxygenase 2, which is essential for prostaglandin production.
1 2D Structure

Hydrocortisone Butyrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] butanoate
2.1.2 InChI
InChI=1S/C25H36O6/c1-4-5-21(30)31-25(20(29)14-26)11-9-18-17-7-6-15-12-16(27)8-10-23(15,2)22(17)19(28)13-24(18,25)3/h12,17-19,22,26,28H,4-11,13-14H2,1-3H3/t17-,18-,19-,22+,23-,24-,25-/m0/s1
2.1.3 InChI Key
BMCQMVFGOVHVNG-TUFAYURCSA-N
2.1.4 Canonical SMILES
CCCC(=O)OC1(CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C)C(=O)CO
2.1.5 Isomeric SMILES
CCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C)C(=O)CO
2.2 Other Identifiers
2.2.1 UNII
05RMF7YPWN
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cortisol 17-butyrate

2. Hydrocortisone 17-butyrate

3. Hydrocortisone-17-butyrate

4. Locoid

2.3.2 Depositor-Supplied Synonyms

1. Hydrocortisone 17-butyrate

2. Cortisol 17-butyrate

3. Hydrocortisone-17-butyrate

4. 13609-67-1

5. Locoid

6. Hydrocortisone-17alpha-butyrate

7. 17-o-butyrylcortisol

8. 11beta,17,21-trihydroxypregn-4-ene-3,20-dione 17-butyrate

9. H-17-b

10. Chebi:31674

11. 05rmf7ypwn

12. Mls000028716

13. Mls001076086

14. Laticort

15. Nsc-758433

16. Alfason

17. Hycortate

18. Lacoidon

19. Smr000058859

20. Bucort

21. Lacoid

22. Dsstox_cid_25896

23. Dsstox_rid_81208

24. Dsstox_gsid_45896

25. 11beta,21-dihydroxy-3,20-dioxopregn-4-en-17-yl Butanoate

26. 11beta,21-dihydroxy-17alpha-butyryloxy-4-pregnene-3,20-dione

27. Hb(sub 17)

28. Cas-13609-67-1

29. Cortisol, 17-butyrate

30. H.17b

31. [(8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Butanoate

32. Einecs 237-093-4

33. Unii-05rmf7ypwn

34. Ncgc00095037-01

35. Locoid (tn)

36. Hydrocortisone-butyrate

37. Opera_id_188

38. Hydrocortisone Butyrate [usan:usp:ban:jan]

39. Butyric Acid Hydrocortisone

40. Epitope Id:119710

41. 11-beta,17-alpha,21-trihydroxy-4-pregnene-3,20-dione 17-alpha-butyrate

42. Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11-beta)-

43. Schembl4695

44. Chembl1683

45. Mls002207122

46. Dtxsid4045896

47. Bdbm323672

48. Hms2231b16

49. Bcp11925

50. Hy-b0983

51. Zinc3977794

52. Tox21_111397

53. Ac-492

54. Hydrocortisone Butyrate (jp17/usp)

55. Hydrocortisone Butyrate [jan]

56. S6590

57. Hydrocortisone Butyrate [usan]

58. Akos015895443

59. Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11.beta.)-

60. Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11beta)-

61. Tox21_111397_1

62. Cs-4474

63. Db14540

64. Hydrocortisone Butyrate [mart.]

65. Hydrocortisone Butyrate [vandf]

66. Nsc 758433

67. Hydrocortisone Butyrate [usp-rs]

68. Hydrocortisone Butyrate [who-dd]

69. Hydrocortisone 17-butyrate [mi]

70. Ncgc00274077-01

71. Us10188667, Example 00013

72. Us10188667, Example 00024

73. (1s,10s,11s,15s,17s,2r,14r)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-ox Otetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-6-en-14-yl Butanoate

74. H1506

75. Hydrocortisone Butyrate [orange Book]

76. D01619

77. Hydrocortisone Butyrate [usp Monograph]

78. 609h671

79. A807026

80. Q5954743

81. W-108252

82. Hydrocortisone 17-butyrate 100 Microg/ml In Methanol

83. Hydrocortisone Butyrate (hydrocortisone 17-butyrate)

84. 11.beta.,17,21-trihydroxypregn-4-ene-3,20-dione 17-butyrate

85. Hydrocortisone Butyrate, United States Pharmacopeia (usp) Reference Standard

86. (8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl Butanoate

87. [(8s,9s,10r,11s,13s,14s,17r)-10,13-dimethyl-11-oxidanyl-17-(2-oxidanylethanoyl)-3-oxidanylidene-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Butanoate

88. Butanoic Acid [(8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-17-(2-hydroxy-1-oxoethyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Ester

2.3.3 Other Synonyms

1. Hydrocortisone Butyrate Propionate

2. Hydrocortisone Buteprate

3.  Hydrocortisone Probutate

4. Pandel

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 432.5 g/mol
Molecular Formula C25H36O6
XLogP33.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass432.25118886 g/mol
Monoisotopic Mass432.25118886 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count31
Formal Charge0
Complexity817
Isotope Atom Count0
Defined Atom Stereocenter Count7
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 3  
Drug NameLOCOID
Active IngredientHYDROCORTISONE BUTYRATE
CompanyPRECISION DERMAT (Application Number: N018514); PRECISION DERMAT (Application Number: N018652); PRECISION DERMAT (Application Number: N019116); PRECISION DERMAT (Application Number: N022076. Patents: 7378405, 7981877)

2 of 3  
Drug NameHYDROCORTISONE BUTYRATE
Active IngredientHYDROCORTISONE BUTYRATE
CompanyACTAVIS MID ATLANTIC (Application Number: A205134); GLENMARK GENERICS (Application Number: A202145); TARO PHARM INDS (Application Number: A076364); TARO PHARM INDS (Application Number: A076654); TARO (Application Number: A076842); TELIGENT PHARMA INC (Application Number: A209556)

3 of 3  
Drug NameLOCOID LIPOCREAM
Active IngredientHYDROCORTISONE BUTYRATE
CompanyPRECISION DERMAT (Application Number: N020769)

4.2 Drug Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). It is also used to treat many immune and allergic disorders, such as arthritis, lupus, severe psoriasis, severe asthma, ulcerative colitis, and Crohn's disease.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Hydrocortisone is the most important human glucocorticoid. It is essential for life and regulates or supports a variety of important cardiovascular, metabolic, immunologic and homeostatic functions. Topical hydrocortisone is used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger a variety of important cardiovascular, metabolic, immunologic and homeostatic effects. Glucocorticoids are distinguished from mineralocorticoids and sex steroids by having different receptors, target cells, and effects. Technically, the term corticosteroid refers to both glucocorticoids and mineralocorticoids, but is often used as a synonym for glucocorticoid. Glucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.


5.2 MeSH Pharmacological Classification

Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AB - Corticosteroids, moderately potent (group ii)

D07AB02 - Hydrocortisone butyrate


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 increase percutaneous absorption.


Route of Elimination

Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.


5.6 Metabolism/Metabolites

Primarily hepatic via CYP3A4


5.7 Biological Half-Life

6-8 hours


5.8 Mechanism of Action

Hydrocortisone binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. The cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In other words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding.


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13-Apr-2021
17-Oct-2022
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