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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

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 It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.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


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ABOUT THIS PAGE

Troglitazone Manufacturers

A Troglitazone manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Troglitazone, including repackagers and relabelers. The FDA regulates Troglitazone manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Troglitazone API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Troglitazone Suppliers

A Troglitazone supplier is an individual or a company that provides Troglitazone active pharmaceutical ingredient (API) or Troglitazone finished formulations upon request. The Troglitazone suppliers may include Troglitazone API manufacturers, exporters, distributors and traders.

click here to find a list of Troglitazone suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Troglitazone USDMF

A Troglitazone DMF (Drug Master File) is a document detailing the whole manufacturing process of Troglitazone active pharmaceutical ingredient (API) in detail. Different forms of Troglitazone DMFs exist exist since differing nations have different regulations, such as Troglitazone USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Troglitazone DMF submitted to regulatory agencies in the US is known as a USDMF. Troglitazone USDMF includes data on Troglitazone's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Troglitazone USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Troglitazone suppliers with USDMF on PharmaCompass.

Troglitazone GMP

Troglitazone Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Troglitazone GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Troglitazone GMP manufacturer or Troglitazone GMP API supplier for your needs.

Troglitazone CoA

A Troglitazone CoA (Certificate of Analysis) is a formal document that attests to Troglitazone's compliance with Troglitazone specifications and serves as a tool for batch-level quality control.

Troglitazone CoA mostly includes findings from lab analyses of a specific batch. For each Troglitazone CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Troglitazone may be tested according to a variety of international standards, such as European Pharmacopoeia (Troglitazone EP), Troglitazone JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Troglitazone USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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