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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

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    06-Sep-2021
    13-Jun-2024
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    DOSAGE - TABLET;ORAL - EQ 2MG BASE

    USFDA APPLICATION NUMBER - 21071

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    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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