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Chemistry

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Also known as: Locorten, 2002-29-1, Locacorten, Flumetasone pivalate, Flumethasone 21-pivalate, Lorinden
Molecular Formula
C27H36F2O6
Molecular Weight
494.6  g/mol
InChI Key
JWRMHDSINXPDHB-OJAGFMMFSA-N
FDA UNII
0DV09X6F21

Flumethasone Pivalate
1 2D Structure

Flumethasone Pivalate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate
2.1.2 InChI
InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1
2.1.3 InChI Key
JWRMHDSINXPDHB-OJAGFMMFSA-N
2.1.4 Canonical SMILES
CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)COC(=O)C(C)(C)C)O)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(C)(C)C)O)C)O)F)C)F
2.2 Other Identifiers
2.2.1 UNII
0DV09X6F21
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cerson

2. Flumethasone Dimethylpropionate

3. Locacorten

4. Locorten

2.3.2 Depositor-Supplied Synonyms

1. Locorten

2. 2002-29-1

3. Locacorten

4. Flumetasone Pivalate

5. Flumethasone 21-pivalate

6. Lorinden

7. Nsc 107680

8. Nsc-107680

9. Mls000069558

10. Mls001077304

11. Chebi:31620

12. 0dv09x6f21

13. Nsc107680

14. Smr000058824

15. Flumethasone-21-pivalate

16. Locorten (tn)

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

18. Flumetasone 21-pivalate

19. Flumethasone Pivalate (usp)

20. Unii-0dv09x6f21

21. 6.alpha.,9.alpha.-difluoro-16.alpha.-methylprednisolone 21-pivalate

22. Flumetasone Pivalate (jan/ban)

23. Flumethasone Pivalate [usan:usp]

24. Ncgc00022408-03

25. Flumethsone Pivalate

26. Einecs 217-901-1

27. Flumethasone-pivalate

28. Flumethasome Pivalate

29. Ks-1138

30. Opera_id_1461

31. Schembl6968

32. [2-[(6s,8s,9r,10s,11s,13s,14s,16r,17r)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate

33. Gtpl7075

34. Chembl1200877

35. 6alpha,9alpha-difluoro-16alpha-methylprednisolone 21-pivalate

36. Flumetasone Pivalate [jan]

37. Hms2231d24

38. Hms3715l14

39. Zinc3977985

40. Flumethasone Pivalate [usan]

41. Flumetasone Pivalate [mart.]

42. Flumetasone Pivalate [who-dd]

43. Akos015964841

44. Ac-2070

45. Ccg-221256

46. Flumethasone 21-pivalate [mi]

47. 6,9-difluoro-11,17-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-yl Pivalate

48. Ncgc00022408-04

49. 6alpha,9-difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-(2,2-dimethylpropionate)

50. 6alpha,9-difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-pivalate

51. 6alpha,9-difluoro-11beta,17-dihydroxy-16alpha-methyl-3,20-dioxopregna-1,4-dien-21-yl 2,2-dimethylpropanoate

52. Flumetasone Pivalate [ep Monograph]

53. Flumethasone Pivalate [orange Book]

54. Flumethasone Pivalate [usp Impurity]

55. D01464

56. E98632

57. 002f291

58. Q-101376

59. Q20817117

60. Flumethasone Pivalate, British Pharmacopoeia (bp) Reference Standard

61. Flumethasone Pivalate, European Pharmacopoeia (ep) Reference Standard

62. Flumethasone Pivalate, United States Pharmacopeia (usp) Reference Standard

63. [2-[(6s,8s,9r,10s,11s,13s,14s,16r,17r)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] 2,2-dimethylpropanoate

64. 2-((6s,9r,10s,11s,13s,16r,17r)-6,9-difluoro-11,17-dihydroxy-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 Pivalate

65. 2-[(1r,2s,8s,10s,11s,13r,14r,15s,17s)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate

66. 6alpha,9alpha-difluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione, 21-pivalate

67. Pregna-1,4-diene-3,20-dione, 21-(2,2-dimethyl-1-oxopropoxy)-6,9-difluoro-11, 17-dihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-

68. Pregna-1,4-diene-3,20-dione, 21-(2,2-dimethyl-1-oxopropoxy)-6,9-difluoro-11,17-dihydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)

69. Pregna-1,4-diene-3,20-dione, 21-(2,2-dimethyl-1-oxopropoxy)-6,9-difluoro-11,17-dihydroxy-16-methyl-, (6alpha,11beta,16alpha)-

70. Pregna-1,4-diene-3,20-dione, 6-alpha,9-difluoro-11-beta,17,21-trihydroxy-16-alpha-methyl-, 21-pivalate

71. Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,17,21-trihydroxy-16alpha-methyl-, 21-pivalate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 494.6 g/mol
Molecular Formula C27H36F2O6
XLogP33.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass494.24799519 g/mol
Monoisotopic Mass494.24799519 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count35
Formal Charge0
Complexity1030
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

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.)


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