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Prestwick3_000619

Prestwick3_000619

Synopsis, Chemistry

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Also known as: 33564-31-7, Psorcon, Florone e, Maxiflor, Apexicon e, Diflorasone di(acetate)

Molecular Formula

C₂₆H₃₂F₂O₇

Molecular Weight

494.5 g/mol

InChI Key

BOBLHFUVNSFZPJ-JOYXJVLSSA-N

FDA UNII

7W2J09SCWX

Diflorasone Diacetate is the acetate salt form of diflorasone, a synthetic glucocorticoid with anti-inflammatory and immunosuppressive properties. Like other glucocorticoids, diflorasone enters the cell by diffusion across the cell membrane and binds to the glucocorticoid receptor (GR) in the cytoplasm. The receptor complex subsequently translocates to the nucleus and activates or represses genes by interacting with short, palindromic DNA sequences called glucocorticoid response element (GRE). Gene activation leads to the exertion of anti-inflammatory effects, e.g. upregulation of IkappaB, while gene repression inhibits production of pro-inflammatory cytokines such as interleukin-1 (IL-1), IL-2 and IL-6, thereby preventing activation of cytotoxic T-lymphocytes.

1 2D Structure

Prestwick3_000619

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-[(6S,8S,9R,10S,11S,13S,14S,16S,17R)-17-acetyloxy-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate

2.1.2 InChI

InChI=1S/C26H32F2O7/c1-13-8-17-18-10-20(27)19-9-16(31)6-7-23(19,4)25(18,28)21(32)11-24(17,5)26(13,35-15(3)30)22(33)12-34-14(2)29/h6-7,9,13,17-18,20-21,32H,8,10-12H2,1-5H3/t13-,17-,18-,20-,21-,23-,24-,25-,26-/m0/s1

2.1.3 InChI Key

BOBLHFUVNSFZPJ-JOYXJVLSSA-N

2.1.4 Canonical SMILES

CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)COC(=O)C)OC(=O)C)C)O)F)C)F

2.1.5 Isomeric SMILES

C[C@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)COC(=O)C)OC(=O)C)C)O)F)C)F

2.2 Other Identifiers

2.2.1 UNII

7W2J09SCWX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Diflorasone

2. Florone

3. Flutone

4. Maxiflor

5. Psorcon

6. Psorcon E

2.3.2 Depositor-Supplied Synonyms

1. 33564-31-7

2. Psorcon

3. Florone E

4. Maxiflor

5. Apexicon E

6. Diflorasone Di(acetate)

7. 7w2j09scwx

8. Mls000069559

9. Mls001076548

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

11. 6alpha,9-difluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-diacetate

12. Chebi:31483

13. U-34865

14. U-34,865

15. Ncgc00022003-03

16. Smr000058814

17. Psorcon E

18. Dsstox_cid_25646

19. Dsstox_rid_81024

20. Dsstox_gsid_45646

21. Apexicon

22. 2-((6s,8s,9r,10s,11s,13s,14s,16s,17r)-17-acetoxy-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl Acetate

23. 6alpha-fluorobetamethasone-17,21 Diacetate

24. Einecs 251-575-1

25. Unii-7w2j09scwx

26. Brn 2318163

27. Pregna-1,4-diene-3,20-dione, 17,21-bis(acetyloxy)-6,9-difluoro-11-hydroxy-16-methyl-, (6.alpha.,11.beta.,16.beta.)-

28. Florone (tn)

29. Psorcon (tn)

30. Cas-33564-31-7

31. Diflorasone Diacetate [usan:usp:jan]

32. Acetic Acid Diflorasone

33. Opera_id_1660

34. Prestwick0_000619

35. Prestwick1_000619

36. Prestwick2_000619

37. Prestwick3_000619

38. Schembl4556

39. Bspbio_000558

40. Diflorasone 17,21-diacetate

41. Regid_for_cid_71414

42. Spbio_002777

43. Bpbio1_000614

44. Gtpl7068

45. Chembl1200545

46. Dtxsid8045646

47. Diflorasone Diacetate [mi]

48. Hms1569l20

49. Hms2096l20

50. Hms2231d10

51. Hms3713l20

52. Diflorasone Diacetate (jp17/usp)

53. Diflorasone Diacetate [jan]

54. 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-16.beta.-methylpregna-1,4-diene-3,20-dione 17,21-diacetate

55. Zinc4212938

56. Diflorasone Diacetate [usan]

57. Tox21_110875

58. Diflorasone Diacetate [vandf]

59. Diflorasone Diacetate [mart.]

60. Akos025402039

61. Diflorasone Diacetate [usp-rs]

62. Diflorasone Diacetate [who-dd]

63. Tox21_110875_1

64. Ac-3515

65. Bcp9000608

66. Ccg-220619

67. Nsc 759267

68. Ncgc00022003-04

69. Ncgc00022003-06

70. (6alpha,11beta,16beta)-6,9-difluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-diene-17,21-diyl Diacetate

71. Pregna-1,4-diene-3,20-dione, 17,21-bis(acetyloxy)-6,9-difluoro-11-hydroxy-16-methyl-, (6alpha,11beta,16beta)-

72. Diflorasone Diacetate [orange Book]

73. Diflorasone Diacetate [usp Impurity]

74. Hy-107961

75. Ab00489907

76. Cs-0031025

77. Diflorasone Diacetate [usp Monograph]

78. D01327

79. E98631

80. Diflorasone Diacetate 100 Microg/ml In Methanol

81. 564d317

82. A821840

83. Sr-01000000122

84. Q-101374

85. Sr-01000000122-3

86. Brd-k17674993-001-03-1

87. Q27881705

88. Diflorasone Diacetate, United States Pharmacopeia (usp) Reference Standard

89. [2-[(6s,8s,9r,10s,11s,13s,14s,16s,17r)-17-acetyloxy-6,9-bis(fluoranyl)-10,13,16-trimethyl-11-oxidanyl-3-oxidanylidene-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxidanylidene-ethyl] Ethanoate

90. 6alpha,9-difluoro-11beta-hydroxy-16beta-methyl-3,20-dioxopregna-1,4-diene-17,21-diyl Diacetate

91. Acetic Acid [2-[(6s,8s,9r,10s,11s,13s,14s,16s,17r)-17-acetyloxy-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Ester

92. Pregna-1,4-diene-3,20-dione, 17,21-bis(acetyloxy)-6,9-difluoro-11-hydroxy-16-methyl-, (6,alpha.,11.beta.,16.beta.)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₂F₂O₇
Molecular Weight	494.5 g/mol
XLogP3	3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	494.21160968 g/mol
Monoisotopic Mass	494.21160968 g/mol
Topological Polar Surface Area	107 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	1050
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
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	Diflorasone diacetate
Drug Label	Each gram of psorcon Ointment contains 0.5 mg diflorasone diacetate in an ointment base. Chemically, diflorasone diacetate is 6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione 17,21-diacetate. The structural formula is repre...
Active Ingredient	Diflorasone diacetate
Dosage Form	Ointment; Cream
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Fougera Pharms; Taro

2 of 2
Drug Name	Diflorasone diacetate
Drug Label	Each gram of psorcon Ointment contains 0.5 mg diflorasone diacetate in an ointment base. Chemically, diflorasone diacetate is 6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione 17,21-diacetate. The structural formula is repre...
Active Ingredient	Diflorasone diacetate
Dosage Form	Ointment; Cream
Route	Topical
Strength	0.05%
Market Status	Prescription
Company	Fougera Pharms; Taro

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

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