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    Troglitazone

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PATENTS & EXCLUSIVITIES

    PharmaCompass
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    2D Structure
    Also known as: 97322-87-7, Rezulin, Romglizone, Prelay, Cs-045, Romozin
    Molecular Formula
    C24H27NO5S
    Molecular Weight
    441.5  g/mol
    InChI Key
    GXPHKUHSUJUWKP-UHFFFAOYSA-N
    A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
    2.1.3 InChI Key
    GXPHKUHSUJUWKP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(C2=C(CCC(O2)(C)COC3=CC=C(C=C3)CC4C(=O)NC(=O)S4)C(=C1O)C)C
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 5-(4-((6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)benzyl)-2,4-thiazolidinedione) - T

    2. Cs 045

    3. Cs-045

    4. Cs045

    5. Prelay

    6. Rezulin

    2.2.2 Depositor-Supplied Synonyms

    1. 97322-87-7

    2. Rezulin

    3. Romglizone

    4. Prelay

    5. Cs-045

    6. Romozin

    7. Noscal

    8. Rezulin (tn)

    9. Cs 045

    10. Gr 92132x

    11. Ccris 8969

    12. Gr92132x

    13. Ci 991

    14. Ci-991

    15. Gr-92132x

    16. Chebi:9753

    17. (+-)-all-rac-5-(p-((6-hydroxy-2,5,7,8-tetramethyl-2-chromanyl)methoxy)benzyl)-2,4-thiazolidinedione

    18. 5-(4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl)thiazolidine-2,4-dione

    19. Troglitazone (cs-045)

    20. (+/-)-5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione

    21. 5-(4-((6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy)benzyl)thiazolidine-2,4-dione

    22. 5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

    23. Ncgc00164445-01

    24. Dsstox_cid_3719

    25. Dsstox_rid_77162

    26. Dsstox_gsid_23719

    27. 2,4-thiazolidinedione, 5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-benzopyran-2-yl)methoxy)phenyl)methyl)-

    28. 5-{4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2h-chromen-2-yl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione

    29. Troglitazona

    30. Troglitazonum

    31. Bdbm50101974

    32. 5-[(4-{[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2h-chromen-2-yl)methyl]oxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

    33. Cas-97322-87-7

    34. Sr-05000000454

    35. 5-[[4-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-benzopyran-2-yl)methoxy]phenyl]methyl]-2,4-thiazolidinedione

    36. Unii-i66zz0zn0e

    37. Brn 4338399

    38. Troglitazone (jan/usan/inn)

    39. Troglitazone [usan:inn:ban]

    40. 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

    41. Cs045

    42. 2,4-thiazolidinedione, 5-[[4-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-benzopyran-2-yl)methoxy]phenyl]methyl]-

    43. Spectrum5_001973

    44. Upcmld-dp017

    45. Schembl4959

    46. I66zz0zn0e

    47. Mls006010817

    48. Gtpl2693

    49. Chembl3542292

    50. Dtxsid8023719

    51. Upcmld-dp017:001

    52. Upcmld-dp017:002

    53. Troglitazone, >=98% (hplc)

    54. Hms2089d22

    55. Hms2093d04

    56. Hms3649g12

    57. Hms3713d08

    58. Bcp06753

    59. Ex-a3782

    60. Tox21_112119

    61. Tox21_300470

    62. Bdbm50088494

    63. Hsci1_000037

    64. S8432

    65. Akos000281116

    66. Akos024457434

    67. Tox21_112119_1

    68. Troglitazone - Cas 97322-87-7

    69. Ccg-208125

    70. Cs-1634

    71. Db00197

    72. Smp2_000224

    73. Ncgc00161599-01

    74. Ncgc00161599-02

    75. Ncgc00161599-03

    76. Ncgc00161599-04

    77. Ncgc00161599-05

    78. Ncgc00161599-06

    79. Ncgc00161599-07

    80. Ncgc00161599-08

    81. Ncgc00161599-09

    82. Ncgc00161599-11

    83. Ncgc00254440-01

    84. Ac-31453

    85. As-56378

    86. Hy-50935

    87. Smr001550129

    88. Db-057670

    89. Ft-0630994

    90. T3920

    91. D00395

    92. H12073

    93. Ab00643330-02

    94. 322t877

    95. A845704

    96. Q7844989

    97. Sr-05000000454-2

    98. Sr-05000000454-3

    99. Sr-05000000454-5

    100. Brd-a13084692-001-02-5

    101. 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidine

    102. 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine -2,4-dione

    103. (5r)-5-[[4-[[(2s)-6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl]methoxy]phenyl]methyl]thiazolidine-2,4-dione

    104. 2,4-thiazolidinedione, 5-[[4-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-benzopyran-2-yl)methoxy]phenyl]methyl]- (9ci)

    105. 5-[[4-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1- Benzopyran-2-yl)methoxy]phenyl]methyl]-2,4-thiazlidinedione

    106. 5-[[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

    107. 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2h-1-benzopyran-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

    108. 5-{4-(6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-yl-methoxy) Benzyl) Thiazolidine-2,4-dione

    2.3 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 441.5 g/mol
    Molecular Formula C24H27NO5S
    XLogP35.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count5
    Exact Mass441.16099414 g/mol
    Monoisotopic Mass441.16099414 g/mol
    Topological Polar Surface Area110 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity681
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of Type II diabetes mellitus. It is used alone or in combination with a sulfonylurea, metformin, or insulin as an adjunct to diet and exercise.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Troglitazone is an oral antihyperglycemic agent which acts primarily by decreasing insulin resistance. Troglitazone is used in the management of type II diabetes (noninsulin-dependent diabetes mellitus (NIDDM) also known as adult-onset diabetes). It improves sensitivity to insulin in muscle and adipose tissue and inhibits hepatic gluconeogenesis. Troglitazone is not chemically or functionally related to either the sulfonylureas, the biguanides, or the g-glucosidase inhibitors. Troglitazone may be used concomitantly with a sulfonylurea or insulin to improve glycemic control.

    5.2 MeSH Pharmacological Classification

    Hypoglycemic Agents

    Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

    5.3 ATC Code

    A - Alimentary tract and metabolism

    A10 - Drugs used in diabetes

    A10B - Blood glucose lowering drugs, excl. insulins

    A10BG - Thiazolidinediones

    A10BG01 - Troglitazone

    5.4 Absorption, Distribution and Excretion

    Absorption

    Absorbed rapidly. Food increases the extent of absorption by 30% to 85%.

    5.5 Metabolism/Metabolites

    A sulfate conjugate metabolite (Metabolite 1) and a quinone metabolite (Metabolite 3) have been detected in the plasma of healthy males. A glucuronide conjugate (Metabolite 2) has been detected in the urine and also in negligible amounts in the plasma. In healthy volunteers and in patients with type 2 diabetes, the steady-state concentration of Metabolite 1 is six to seven times that of troglitazone and Metabolite 3. In in vivo drug interaction studies, troglitazone has been shown to induce cytochrome P450 CYP3A4 at clinically relevant doses.

    Troglitazone has known human metabolites that include (2S,3S,4S,5R)-6-[[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.6 Biological Half-Life

    16-34 hours

    5.7 Mechanism of Action

    Troglitazone is a thiazolidinedione antidiabetic agent that lowers blood glucose by improving target cell response to insulin. It has a unique mechanism of action that is dependent on the presence of insulin for activity. Troglitazone decreases hepatic glucose output and increases insulin dependent glucose disposal in skeletal muscle. Its mechanism of action is thought to involve binding to nuclear receptors (PPAR) that regulate the transcription of a number of insulin responsive genes critical for the control of glucose and lipid metabolism. Troglitazone is a ligand to both PPAR and PPAR, with a highter affinity for PPAR. The drug also contains an -tocopheroyl moiety, potentially giving it vitamin E-like activity. Troglitazone has been shown to reduce inflammation, and is associated with a decrase in nuclear factor kappa-B (NF-B) and a concomitant increase in its inhibitor (IB). Unlike sulfonylureas, troglitazone is not an insulin secretagogue.