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Chemistry

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Also known as: 5611-51-8, Aristospan, Lederspan, Tatba, Cl 34433, Tiamcinoloni hexacetonidum [inn]
Molecular Formula
C30H41FO7
Molecular Weight
532.6  g/mol
InChI Key
TZIZWYVVGLXXFV-FLRHRWPCSA-N
FDA UNII
I7GT1U99Y9

Triamcinolone Hexacetonide
Triamcinolone Hexacetonide is the hexacetonide salt form of triamcinolone, a synthetic glucocorticosteroid with immunosuppressive and anti-inflammatory activity. Triamcinolone hexacetonide binds to specific cytosolic glucocorticoid receptors and subsequently interacts with glucocorticoid receptor response element on DNA and alters gene expression. This results in an induction of the synthesis of certain anti-inflammatory proteins while inhibiting the synthesis of certain inflammatory mediators. Consequently, an overall reduction in chronic inflammation and autoimmune reactions are accomplished.
1 2D Structure

Triamcinolone Hexacetonide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 3,3-dimethylbutanoate
2.1.2 InChI
InChI=1S/C30H41FO7/c1-25(2,3)15-24(35)36-16-22(34)30-23(37-26(4,5)38-30)13-20-19-9-8-17-12-18(32)10-11-27(17,6)29(19,31)21(33)14-28(20,30)7/h10-12,19-21,23,33H,8-9,13-16H2,1-7H3/t19-,20-,21-,23+,27-,28-,29-,30+/m0/s1
2.1.3 InChI Key
TZIZWYVVGLXXFV-FLRHRWPCSA-N
2.1.4 Canonical SMILES
CC1(OC2CC3C4CCC5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)COC(=O)CC(C)(C)C)C)O)F)C)C
2.1.5 Isomeric SMILES
C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)COC(=O)CC(C)(C)C)CCC5=CC(=O)C=C[C@@]53C)F)O
2.2 Other Identifiers
2.2.1 UNII
I7GT1U99Y9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9-fluoro-11 Beta,16 Alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone, 21-(3,3-dimethylbutyrate)

2. Aristospan

2.3.2 Depositor-Supplied Synonyms

1. 5611-51-8

2. Aristospan

3. Lederspan

4. Tatba

5. Cl 34433

6. Tiamcinoloni Hexacetonidum [inn]

7. Chebi:9670

8. I7gt1u99y9

9. [2-[(1s,2s,4r,8s,9s,11s,12r,13s)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 3,3-dimethylbutanoate

10. Aristospan (tn)

11. Pregna-1,4-diene-3,20-dione,21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11b,16a)-

12. Triamcinolone Esacetonide

13. Tiamcinoloni Hexacetonidum

14. Triamcinoloni Hexacetonidum

15. Hexacetonide De Triamcinolone

16. Hexacetonido De Triancinolona

17. Unii-i7gt1u99y9

18. Triamcinolone Esacetonide [dcit]

19. Ncgc00182544-01

20. (11?,16?)-21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

21. Einecs 227-031-4

22. Brn 1413888

23. Triamcinoloni Hexacetonidum [inn-latin]

24. Cl-34433

25. Hexacetonide De Triamcinolone [inn-french]

26. Triamcinolone-hexacetonide

27. Hexacetonido De Triancinolona [inn-spanish]

28. Triamcinolone Hexace-tonide

29. Schembl7543

30. Triamcinolone Hexacetonide [usan:usp:inn:ban]

31. Dsstox_cid_28560

32. Dsstox_rid_82832

33. Dsstox_gsid_48634

34. 5-19-06-00569 (beilstein Handbook Reference)

35. Triamcinolonehexacetonide

36. Chembl1200878

37. Dtxsid0048634

38. 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone 21-(3,3-dimethylbutyrate)

39. Pregna-1,4-diene-3,20-dione, 21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11.beta.,16.alpha.)-

40. Zinc4097475

41. Tox21_112979

42. Hy-u00103

43. Triamcinolone Hexacetonide (usp/inn)

44. Cs-7139

45. Triamcinolone Hexacetonide [mi]

46. Triamcinolone Hexacetonide [inn]

47. Triamcinolone Hexacetonide [usan]

48. 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Acetone 21-(3,3-dimethylbutyrate)

49. Pregna-1,4-diene-3,20-dione, 21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11beta,16alpha)-

50. Triamcinolone Hexacetonide [mart.]

51. Triamcinolone Hexacetonide [vandf]

52. Cas-5611-51-8

53. Triamcinolone Hexacetonide [usp-rs]

54. Triamcinolone Hexacetonide [who-dd]

55. C08185

56. D00985

57. Triamcinolone Hexacetonide [orange Book]

58. Triamcinolone Hexacetonide [ep Monograph]

59. Triamcinolone Hexacetonide [usp Impurity]

60. Triamcinolone Hexacetonide [usp Monograph]

61. Q1593246

62. (11beta,16alpha)-21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))pregna-1,4-diene-3,20-dione

63. Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,16-alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone, 21-(3,3-dimethylbutyrate)

64. Pregna-1,4-diene-3,20-dione,21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-,(11b,16a)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 532.6 g/mol
Molecular Formula C30H41FO7
XLogP34.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count6
Exact Mass532.28363180 g/mol
Monoisotopic Mass532.28363180 g/mol
Topological Polar Surface Area99.1 Ų
Heavy Atom Count38
Formal Charge0
Complexity1130
Isotope Atom Count0
Defined Atom Stereocenter Count8
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

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

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DOSAGE - INJECTABLE;INJECTION - 20MG/ML **Fed...DOSAGE - INJECTABLE;INJECTION - 20MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 16466

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DOSAGE - INJECTABLE;INJECTION - 5MG/ML **Fede...DOSAGE - INJECTABLE;INJECTION - 5MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 16466

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