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RTA 402

RTA 402

Synopsis, Chemistry

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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

RTA 402

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 Formula	C₃₂H₄₃NO₄
Molecular Weight	505.7 g/mol
XLogP3	6.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	505.31920885 g/mol
Monoisotopic Mass	505.31920885 g/mol
Topological Polar Surface Area	84.2 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	1210
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.