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Troglitazone

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ACTIVE PHARMA INGREDIENTS

2 API Suppliers, 2 USDMF

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2 USDMF

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6 FDF Dossiers, 6 FDA Orange Book

6 FDF Dossiers
6 FDA Orange Book

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6 Health Canada Patents

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6 Health Canada Patents

Synopsis

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Chemistry

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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 It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.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

Troglitazone

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 Formula	C₂₄H₂₇NO₅S
Molecular Weight	441.5 g/mol
XLogP3	5.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	441.16099414 g/mol
Monoisotopic Mass	441.16099414 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	681
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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