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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]

    DRUG PRODUCT COMPOSITIONS

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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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