Fluorometholone Acetate

Synopsis, Chemistry

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Also known as: 3801-06-7, Eflone, Oxylone acetate, Flarex, Fluorometholone 17-acetate, Nsc 47438

Molecular Formula

C₂₄H₃₁FO₅

Molecular Weight

418.5 g/mol

InChI Key

YRFXGQHBPBMFHW-SBTZIJSASA-N

FDA UNII

9I50C3I3OK

Fluorometholone Acetate is the acetate salt form of fluorometholone, a synthetic glucocorticoid with anti-inflammatory and anti-allergic properties. Fluorometholone acetate exerts its effect by interacting with cytoplasmic glucocorticoid receptors and subsequently activates glucocorticoid receptor mediated gene expression. The synthesis of certain anti-inflammatory proteins is induced while the synthesis of certain inflammatory mediators is inhibited. As a result, there is an overall reduction in chronic inflammation and autoimmune reactions.

1 2D Structure

Fluorometholone Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C24H31FO5/c1-13-10-19-17-7-9-23(14(2)26,30-15(3)27)22(17,5)12-20(29)24(19,25)21(4)8-6-16(28)11-18(13)21/h6,8,11,13,17,19-20,29H,7,9-10,12H2,1-5H3/t13-,17-,19-,20-,21-,22-,23-,24-/m0/s1

2.1.3 InChI Key

YRFXGQHBPBMFHW-SBTZIJSASA-N

2.1.4 Canonical SMILES

CC1CC2C3CCC(C3(CC(C2(C4(C1=CC(=O)C=C4)C)F)O)C)(C(=O)C)OC(=O)C

2.1.5 Isomeric SMILES

C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@]2([C@@]4(C1=CC(=O)C=C4)C)F)O)C)(C(=O)C)OC(=O)C

2.2 Other Identifiers

2.2.1 UNII

9I50C3I3OK

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 3801-06-7

2. Eflone

3. Oxylone Acetate

4. Flarex

5. Fluorometholone 17-acetate

6. Nsc 47438

7. Nsc-47438

8. 9-fluoro-11beta,17-dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione 17-acetate

9. 9i50c3i3ok

10. Chebi:78354

11. U-17323

12. Fluorometholone Acetate [usan:usp]

13. U-17,323

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

15. 6alpha-methyl-9alpha-fluoro-17-acetoxy-21-deoxyprednisolone

16. Ai3-52814

17. Nsc47438

18. Flarex (tn)

19. Fluorometholone-acetate

20. Unii-9i50c3i3ok

21. Schembl43184

22. U 17323

23. Fluorometholone Acetate (usp)

24. Fluorometholone Acetate [usan]

25. Chembl1201064

26. Dtxsid20191424

27. Hy-b1471

28. Zinc4213357

29. Einecs 223-270-3

30. Mfcd00866062

31. S4228

32. Akos025401542

33. Ac-2172

34. Ccg-268873

35. Fluorometholone Acetate [mart.]

36. Fluorometholone Acetate [vandf]

37. Fluorometholone Acetate [usp-rs]

38. Fluorometholone Acetate [who-dd]

39. Fluorometholone 17-acetate [mi]

40. Ncgc00373228-02

41. Bs-16978

42. Nci60_004118

43. Cs-0013170

44. Fluorometholone Acetate [orange Book]

45. Sw219098-1

46. D04221

47. D81740

48. Fluorometholone Acetate [usp Monograph]

49. Ab00641960_02

50. 801f067

51. Fluorometholone Acetate 100 Microg/ml In Methanol

52. Tobrasone Component Fluorometholone Acetate

53. U 17,323

54. Fluorometholone Acetate 100 Microg/ml In Acetonitrile

55. Fluorometholone Acetate Component Of Tobrasone

56. Q27105082

57. Progesterone,17-dihydroxy-6.alpha.-methyl-,17-acetate

58. (6alpha,11beta)-17-(acetyloxy)-9-fluoro-11-hydroxy-6-methylpregna-1,4-diene-3,20-dione

59. (6alpha,11beta)-9-fluoro-11-hydroxy-6-methyl-3,20-dioxopregna-1,4-dien-17-yl Acetate

60. 17-(acetyloxy)-9-fluoro-11beta-hydroxy-6alpha-methylpregna-1,4-diene-3,20-dione

61. 9-fluoro-11beta-hydroxy-6alpha-methyl-3,20-dioxopregna-1,4-dien-17-yl Acetate

62. Pregna-1,20-dione, 17-(acetyloxy)-9-fluoro-11-hydroxy-6-methyl-, (6.alpha.,11.beta.)-

63. Pregna-1,20-dione, 9-fluoro-11.beta.,17-dihydroxy-6.alpha.-methyl-, 17-acetate

64. (1r,2s,8s,10s,11s,14r,15s,17s)-14-acetyl-1-fluoro-17-hydroxy-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl Acetate

65. 9-fluoro-11.beta.,17-dihydroxy-6.alpha.-methylpregna-1,4-diene-3,20-dione 17-acetate

66. Pregna-1,4-diene-3,20-dione, 17-(acetyloxy)-9-fluoro-11-hydroxy-6-methyl-, (6.alpha.,11.beta.)-

67. Pregna-1,4-diene-3,20-dione, 17-(acetyloxy)-9-fluoro-11-hydroxy-6-methyl-, (6alpha,11beta)-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₁FO₅
Molecular Weight	418.5 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	418.21555225 g/mol
Monoisotopic Mass	418.21555225 g/mol
Topological Polar Surface Area	80.7 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	892
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