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    Bardoxolone Methyl

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    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 218600-53-4, Cddo-me, Cddo methyl ester, Rta 402, Nsc 713200, Cddo-methyl ester
    Molecular Formula
    C32H43NO4
    Molecular Weight
    505.7  g/mol
    InChI Key
    WPTTVJLTNAWYAO-KPOXMGGZSA-N
    FDA UNII
    CEG1Q6OGU1
    Bardoxolone Methyl is the methyl ester form of bardoxolone, a synthetic triterpenoid compound with potential antineoplastic and anti-inflammatory activities. Bardoxolone blocks the synthesis of inducible nitric oxide synthase (iNOS) and inducible cyclooxygenase (COX-2), two enzymes involved in inflammation and carcinogenesis. This agent also inhibits the interleukin-1 (IL-1)-induced expression of the pro-inflammatory proteins matrix metalloproteinase-1 (MMP-1) and matrix metalloproteinase-13 (MMP-13) and the expression of Bcl-3; Bcl-3 is an IL-1-responsive gene that preferentially contributes to MMP-1 gene expression.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylate
    2.1.2 InChI
    InChI=1S/C32H43NO4/c1-27(2)11-13-32(26(36)37-8)14-12-31(7)24(20(32)17-27)21(34)15-23-29(5)16-19(18-33)25(35)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,29-,30+,31+,32-/m0/s1
    2.1.3 InChI Key
    WPTTVJLTNAWYAO-KPOXMGGZSA-N
    2.1.4 Canonical SMILES
    CC1(CCC2(CCC3(C(C2C1)C(=O)C=C4C3(CCC5C4(C=C(C(=O)C5(C)C)C#N)C)C)C)C(=O)OC)C
    2.1.5 Isomeric SMILES
    C[C@@]12CC[C@]3(CCC(C[C@H]3[C@H]1C(=O)C=C4[C@]2(CC[C@@H]5[C@@]4(C=C(C(=O)C5(C)C)C#N)C)C)(C)C)C(=O)OC
    2.2 Other Identifiers
    2.2.1 UNII
    CEG1Q6OGU1
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-cyano-3,12-dioxoolean-1,9-dien-28-oic Acid Methyl Ester

    2. Cddo Methyl Ester

    3. Cddo-me

    4. Methyl 2-cyano-3,12-dioxoolean-1,9-dien-28-oate

    5. Rta-402

    2.3.2 Depositor-Supplied Synonyms

    1. 218600-53-4

    2. Cddo-me

    3. Cddo Methyl Ester

    4. Rta 402

    5. Nsc 713200

    6. Cddo-methyl Ester

    7. Rta-402

    8. Nsc713200

    9. Rta402

    10. Methyl (4as,6ar,6bs,8ar,12as,14ar,14bs)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylate

    11. Tp-155

    12. Ceg1q6ogu1

    13. Bardoxolone Methyl [usan]

    14. Nsc-713200

    15. Methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate

    16. 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic Acid Methyl Ester

    17. Methyl (4as,6ar,6bs,12as,14ar,14br)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylate

    18. Bardoxolone-methyl

    19. (4as,6ar,6bs,8ar,12as,14ar,14bs)-methyl 11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carboxylate

    20. Mfcd11983137

    21. Ncgc00186460-01

    22. Bardoxolone (methyl)

    23. Bardoxolone Methyl Ester

    24. Unii-ceg1q6ogu1

    25. Cddo-me, 2

    26. Dsstox_cid_28690

    27. Dsstox_rid_82960

    28. Dsstox_gsid_48764

    29. Methyl 2-cyano-3,12-dioxoolean-1,9-dien-28-oate

    30. Gtpl3443

    31. Bardoxolone Methyl (jan/usan)

    32. Bardoxolone Methyl [jan]

    33. Chembl1762621

    34. Dtxsid5048764

    35. Schembl12521530

    36. Chebi:177406

    37. 2-cyano-3,12-dioxoolean-1,9-dien-28-oic Acid Methyl Ester

    38. 2-cyano-3,12-dioxooleana-1,9-dien-28-oic Acid Methyl Ester

    39. Bdbm217379

    40. Bardoxolone Methyl [who-dd]

    41. Bcp04660

    42. Zinc3982151

    43. Tox21_113229

    44. S8078

    45. Bardoxolone Methyl Ester [mi]

    46. Akos025401880

    47. Ccg-269743

    48. Cs-0598

    49. Db05983

    50. Cddo Methyl Ester, >=98% (hplc)

    51. Ac-26830

    52. Csa:218600-53-4;bardoxolone Methyl

    53. Hy-13324

    54. Cas-218600-53-4

    55. D09585

    56. Nsc 713200; Rta 402; Cddo Methyl Ester

    57. A847580

    58. Q4860208

    59. (+)-methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate

    60. (4as,6ar,6bs,8ar,12as,14bs)-methyl 11-cyano-2,2,6a,6b,9,9,12a-he

    61. Oleana-1,9(11)-dien-28-oic Acid, 2-cyano-3,12-dioxo-, Methyl Ester

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 505.7 g/mol
    Molecular Formula C32H43NO4
    XLogP36.7
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass505.31920885 g/mol
    Monoisotopic Mass505.31920885 g/mol
    Topological Polar Surface Area84.2 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity1210
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in lymphoma (unspecified), multiple myeloma, and solid tumors.

    Treatment of Alport syndrome

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    RTA 402 inhibits the activity of nuclear factor kappa-B (NF-kB) activated by tumor necrosis factor (TNF) and other inflammatory agents in a variety of cancer cells. It is a novel targeted cancer therapy with a unique mechanism of action. It exploits fundamental physiological differences between cancerous and noncancerous cells by modulating oxidative stress response pathways. As a result, the drug is toxic to cancer cells but induces protective antioxidant and anti-inflammatory responses in normal cells.