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Chemistry

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Also known as: 155141-29-0, Avandia, Rosiglitazone (maleate), Rosiglitazone maleate [usan], Brl-49653c, Brl 49653c
Molecular Formula
C22H23N3O7S
Molecular Weight
473.5  g/mol
InChI Key
SUFUKZSWUHZXAV-BTJKTKAUSA-N
FDA UNII
KX2339DP44

Rosiglitazone Maleate
A thiazolidinedione that functions as a selective agonist for PPAR GAMMA. It improves INSULIN SENSITIVITY in adipose tissue, skeletal muscle, and the liver of patients with TYPE 2 DIABETES MELLITUS.
1 2D Structure

Rosiglitazone Maleate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(Z)-but-2-enedioic acid;5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
2.1.2 InChI
InChI=1S/C18H19N3O3S.C4H4O4/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15;5-3(6)1-2-4(7)8/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1-
2.1.3 InChI Key
SUFUKZSWUHZXAV-BTJKTKAUSA-N
2.1.4 Canonical SMILES
CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3.C(=CC(=O)O)C(=O)O
2.1.5 Isomeric SMILES
CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3.C(=C\C(=O)O)\C(=O)O
2.2 Other Identifiers
2.2.1 UNII
KX2339DP44
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5-((4-(2-methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate

2. Avandia

3. Brl 49653

4. Brl-49653

5. Brl49653

6. Rosiglitazone

2.3.2 Depositor-Supplied Synonyms

1. 155141-29-0

2. Avandia

3. Rosiglitazone (maleate)

4. Rosiglitazone Maleate [usan]

5. Brl-49653c

6. Brl 49653c

7. Rosiglitzazone Maleate

8. 5-(4-(2-(methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione Maleate

9. Brl-49653-c

10. Nsc-717764

11. Kx2339dp44

12. Avandamet

13. 2,4-thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-, (2z)-2-butenedioate (1:1)

14. Nyracta

15. Rosiglitazone Xr

16. Venvia

17. Chebi:8892

18. Brl 49653-c

19. (2z)-but-2-enedioic Acid; 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

20. (z)-but-2-enedioic Acid;5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

21. 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Maleate

22. Smr000471612

23. Avandia (tn)

24. Unii-kx2339dp44

25. 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione Maleate

26. 5-[4-[2-[n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione Maleate

27. Rosiglitazonemaleate

28. 2,4-thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-, (2z)-2-butenedioate (1:1)

29. (+-)-5-(p-(2-(methyl-2-pyridylamino)ethoxy)benzyl)-2,4-thiazolidinedione Maleate (1:1)

30. 1217260-35-9

31. 5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione; But-2-enedioic Acid

32. Dsstox_cid_3569

33. Chembl843

34. Dsstox_rid_77086

35. Dsstox_gsid_23569

36. Schembl19023

37. Rosiglitazone Maleate- Bio-x

38. Mls001306472

39. Mls001401426

40. Dtxsid2023569

41. Rosiglitazone Maleate (jan/usp)

42. Hms2051b11

43. Hms2233i10

44. Hms3884h04

45. Rosiglitazone Maleate [mi]

46. Rosiglitazone Maleate [jan]

47. Tox21_302367

48. Ac-737

49. Mfcd03427306

50. Nsc717764

51. Rosiglitazone Maleate [vandf]

52. S2505

53. Rosiglitazone Maleate [mart.]

54. Akos015961534

55. Rosiglitazone Maleate [usp-rs]

56. Rosiglitazone Maleate [who-dd]

57. Ccg-100943

58. Ccg-208126

59. Cs-1692

60. Ks-5027

61. Nc00193

62. Nsc 717764

63. Ncgc00255233-01

64. 5-{[4-({2-[methyl(pyridin-2-yl)amino]ethyl}oxy)phenyl]methyl}-1,3-thiazolidine-2,4-dione (2z)-but-2-enedioate

65. Br164376

66. Hy-14600

67. Rosiglitazone Maleate [orange Book]

68. Cas-155141-29-0

69. Rosiglitazone Maleate [usp Monograph]

70. Sw197573-4

71. D00596

72. Rosiglitazone Maleate 100 Microg/ml In Methanol

73. 141r290

74. A809615

75. Q27888042

76. 2, 5-[[4-[2-(methyl-2-pyridinylamino) Ethoxy]phenyl]methyl]-, (2z)-2-butenedioate (1:1)

77. 5-[4-[2-[n-methyl-n-(2-pyridyl)amino]ethoxy]phenyl Methyl]thiazolidine-2,4-dione Maleate

78. 5-{4-[2-(methylpyridin-2-ylamino)ethoxy]benzyl}thiazolidine-2,4-dione Maleate

79. (+/-)-5-(p-(2-(methyl-2-pyridylamino)ethoxy)benzyl)-2,4-thiazolidinedione Maleate (1:1)

80. (z)-but-2-enedioate;2-[4-[(2,4-dioxo-1,3-thiazolidin-3-ium-5-yl)methyl]phenoxy]ethyl-methyl-pyridin-2-ylazanium

81. 5-((4-(2-(n-methyl-n-2-pyridylamino)ethoxy)phenyl)methyl)thiazolidine-2,4-dione Maleate

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 473.5 g/mol
Molecular Formula C22H23N3O7S
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count9
Exact Mass473.12567125 g/mol
Monoisotopic Mass473.12567125 g/mol
Topological Polar Surface Area171 Ų
Heavy Atom Count33
Formal Charge0
Complexity588
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAvandaryl
PubMed HealthRosiglitazone (By mouth)
Drug ClassesAntidiabetic
Active Ingredientrosiglitazone maleate; Glimepiride
Dosage FormTablet
RouteOral
Strength4mg; 2mg; 1mg; 8mg
Market StatusPrescription
CompanySb Pharmco

2 of 6  
Drug NameAvandia
Drug LabelAVANDIA (rosiglitazone maleate) is an oral antidiabetic agent which acts primarily by increasing insulin sensitivity. AVANDIA improves glycemic control while reducing circulating insulin levels. Rosiglitazone maleate is not chemically or functionally...
Active IngredientRosiglitazone maleate
Dosage FormTablet
RouteOral
Strengtheq 4mg base; eq 2mg base; eq 8mg base
Market StatusPrescription
CompanySb Pharmco

3 of 6  
Drug NameRosiglitazone maleate
PubMed HealthRosiglitazone/Glimepiride (By mouth)
Drug ClassesAntidiabetic
Drug LabelAVANDIA (rosiglitazone maleate) is an oral antidiabetic agent which acts primarily by increasing insulin sensitivity. AVANDIA improves glycemic control while reducing circulating insulin levels. Rosiglitazone maleate is not chemically or functionally...
Active IngredientRosiglitazone maleate
Dosage FormTablet
Routeoral; Oral
Strengtheq 4mg base; eq 2mg base; 8mg; 4mg; 2mg; eq 8mg base
Market StatusTentative Approval; Prescription
CompanyMylan Pharma; Teva; Sandoz; Hikma Pharms; Roxane

4 of 6  
Drug NameAvandaryl
PubMed HealthRosiglitazone (By mouth)
Drug ClassesAntidiabetic
Active Ingredientrosiglitazone maleate; Glimepiride
Dosage FormTablet
RouteOral
Strength4mg; 2mg; 1mg; 8mg
Market StatusPrescription
CompanySb Pharmco

5 of 6  
Drug NameAvandia
Drug LabelAVANDIA (rosiglitazone maleate) is an oral antidiabetic agent which acts primarily by increasing insulin sensitivity. AVANDIA improves glycemic control while reducing circulating insulin levels. Rosiglitazone maleate is not chemically or functionally...
Active IngredientRosiglitazone maleate
Dosage FormTablet
RouteOral
Strengtheq 4mg base; eq 2mg base; eq 8mg base
Market StatusPrescription
CompanySb Pharmco

6 of 6  
Drug NameRosiglitazone maleate
PubMed HealthRosiglitazone/Glimepiride (By mouth)
Drug ClassesAntidiabetic
Drug LabelAVANDIA (rosiglitazone maleate) is an oral antidiabetic agent which acts primarily by increasing insulin sensitivity. AVANDIA improves glycemic control while reducing circulating insulin levels. Rosiglitazone maleate is not chemically or functionally...
Active IngredientRosiglitazone maleate
Dosage FormTablet
Routeoral; Oral
Strengtheq 4mg base; eq 2mg base; 8mg; 4mg; 2mg; eq 8mg base
Market StatusTentative Approval; Prescription
CompanyMylan Pharma; Teva; Sandoz; Hikma Pharms; Roxane

4.2 Drug Indication

AVANDAMET is indicated in the treatment of type 2 diabetes mellitus patients, particularly overweight patients:

- who are unable to achieve sufficient glycaemic control at their maximally tolerated dose of oral metformin alone.

- in triple oral therapy with sulphonylurea in patients with insufficient glycaemic control despite dual oral therapy with their maximally tolerated dose of metformin and a sulphonylurea (see section 4. 4).


Rosiglitazone is indicated in the treatment of type 2 diabetes mellitus:

as monotherapy

-in patients (particularly overweight patients) inadequately controlled by diet and exercise for whom metformin is inappropriate because of contraindications or intolerance

as dual oral therapy in combination with

-metformin, in patients (particularly overweight patients) with insufficient glycaemic control despite maximal tolerated dose of monotherapy with metformin

-a sulphonylurea, only in patients who show intolerance to metformin or for whom metformin is contraindicated, with insufficient glycaemic control despite monotherapy with a sulphonylurea

as triple oral therapy in combination with

-metformin and a sulphonylurea, in patients (particularly overweight patients) with insufficient glycaemic control despite dual oral therapy (see section 4. 4).


Rosiglitazone is indicated as oral monotherapy in type 2 diabetes mellitus patients, particularly overweight patients, inadequately controlled by diet and exercise for whom metformin is inappropriate because of contraindications or intolerance.

Rosiglitazone is also indicated for oral combination treatment in type 2 diabetes mellitus patients with insufficient glycaemic control despite maximal tolerated dose of oral monotherapy with either metformin or a sulphonylurea:

- in combination with metformin particularly in overweight patients.

- in combination with a sulphonylurea only in patients who show intolerance to metformin or for whom metformin is contraindicated.


Rosiglitazone is indicated as oral monotherapy in type 2 diabetes mellitus patients, particularly overweight patients, inadequately controlled by diet and exercise for whom metformin is inappropriate because of contraindications or intolerance.

Rosiglitazone is also indicated for oral combination treatment in type 2 diabetes mellitus patients with insufficient glycaemic control despite maximal tolerated dose of oral monotherapy with either metformin or a sulphonylurea:

- in combination with metformin particularly in overweight patients.

- in combination with a sulphonylurea only in patients who show intolerance to metformin or for whom metformin is contraindicated.


Alzheimer's Disease


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Hypoglycemic Agents

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


5.2 ATC Code

A10BD03


A10BG02


A10BG02


A10BG02


API Reference Price

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22-Oct-2022
13-Jun-2024
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DOSAGE - TABLET;ORAL - EQ 2MG BASE

USFDA APPLICATION NUMBER - 21071

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DOSAGE - TABLET;ORAL - EQ 4MG BASE

USFDA APPLICATION NUMBER - 21071

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DOSAGE - TABLET;ORAL - EQ 8MG BASE **Federal ...DOSAGE - TABLET;ORAL - EQ 8MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21071

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