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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
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

Bardoxolone Methyl

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.


Drugs in Development

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Details:

RTA 402 (bardoxolone methyl) is a small-molecule compound licensed from Reata Pharmaceuticals has been designated as a "SAKIGAKE Designation" program for the treatment of diabetic kidney disease, a Phase III clinical study for the indication in Japan.


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Nephrology Brand Name: RTA 402

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Reata Pharmaceuticals

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable May 10, 2023

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01

Kyowa Kirin

Japan
arrow
Duphat
Not Confirmed

Kyowa Kirin

Japan
arrow
Duphat
Not Confirmed

Details : RTA 402 (bardoxolone methyl) is a small-molecule compound licensed from Reata Pharmaceuticals has been designated as a "SAKIGAKE Designation" program for the treatment of diabetic kidney disease, a Phase III clinical study for the indication in Japan.

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Not Applicable

May 10, 2023

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Details:

Bardoxolone is orally administered activator of Nrf2, a transcription factor that induces molecular pathways that promote the resolution of inflammation by restoring mitochondrial function, reducing oxidative stress, and inhibiting pro-inflammatory signaling.


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Nephrology Brand Name: RTA 402

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable February 25, 2022

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02

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Bardoxolone is orally administered activator of Nrf2, a transcription factor that induces molecular pathways that promote the resolution of inflammation by restoring mitochondrial function, reducing oxidative stress, and inhibiting pro-inflammatory signa...

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Not Applicable

February 25, 2022

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Details:

USFDA revealed an unflattering opinion of the company’s experimental drug RTA 402 (Bardoxolone methyl) for the treatment of patients with chronic kidney disease (“CKD”) caused by Alport syndrome.


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Genetic Disease Brand Name: RTA 402

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable December 08, 2021

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03

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : USFDA revealed an unflattering opinion of the company’s experimental drug RTA 402 (Bardoxolone methyl) for the treatment of patients with chronic kidney disease (“CKD”) caused by Alport syndrome.

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Not Applicable

December 08, 2021

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Details:

If approved, bardoxolone would become the first therapy specifically indicated for the treatment of CKD caused by Alport syndrome.


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Genetic Disease Brand Name: RTA 402

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 01, 2021

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04

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : If approved, bardoxolone would become the first therapy specifically indicated for the treatment of CKD caused by Alport syndrome.

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 01, 2021

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Details:

Company Plans to submit NDA for bardoxolone in Alport syndrome during fourth quarter of 2020 for accelerated approval based on the one-year data from the Phase 3 portion of CARDINAL.


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Genetic Disease Brand Name: RTA 402

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable November 09, 2020

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05

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Company Plans to submit NDA for bardoxolone in Alport syndrome during fourth quarter of 2020 for accelerated approval based on the one-year data from the Phase 3 portion of CARDINAL.

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Not Applicable

November 09, 2020

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Details:

Bardoxolone achieved the year 2 primary and key secondary endpoints with statistically significant improvements in EGFR as compared to placebo at week 100 and week 104.


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Genetic Disease Brand Name: RTA 402

Study Phase: Phase II/ Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable November 09, 2020

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06

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Bardoxolone achieved the year 2 primary and key secondary endpoints with statistically significant improvements in EGFR as compared to placebo at week 100 and week 104.

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Not Applicable

November 09, 2020

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Details:

Researchers at NYU Grossman School of Medicine led by Sripal Bangalore, MD, interventional cardiologist and professor of Medicine, are initiating an Investigator-Sponsored Trial known as BARCONA, to study the effect of bardoxolone methyl in patients suffering from COVID-19.


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Infections and Infectious Diseases Brand Name: RTA 402

Study Phase: PreclinicalProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable July 28, 2020

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07

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Researchers at NYU Grossman School of Medicine led by Sripal Bangalore, MD, interventional cardiologist and professor of Medicine, are initiating an Investigator-Sponsored Trial known as BARCONA, to study the effect of bardoxolone methyl in patients suff...

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Not Applicable

July 28, 2020

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Details:

Financing from Blackstone will Advance Reata's Bardoxolone as the First Potential Therapy for Alport Syndrome, as well as Continue Development for Other Rare and Serious Forms of Chronic Kidney Disease


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Genetic Disease Brand Name: RTA 402

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Blackstone Life Sciences

Deal Size: $350.0 million Upfront Cash: Undisclosed

Deal Type: Financing June 11, 2020

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08

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Financing from Blackstone will Advance Reata's Bardoxolone as the First Potential Therapy for Alport Syndrome, as well as Continue Development for Other Rare and Serious Forms of Chronic Kidney Disease

Brand Name : RTA 402

Molecule Type : Small molecule

Upfront Cash : Undisclosed

June 11, 2020

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Details:

Company has decided to stop the Phase 3 CATALYST study of bardoxolone methyl (bardoxolone) in patients with connective tissue disease-associated pulmonary arterial hypertension (CTD-PAH).


Lead Product(s): Bardoxolone Methyl

Therapeutic Area: Cardiology/Vascular Diseases Brand Name: Undisclosed

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 30, 2020

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09

Duphat
Not Confirmed
Duphat
Not Confirmed

Details : Company has decided to stop the Phase 3 CATALYST study of bardoxolone methyl (bardoxolone) in patients with connective tissue disease-associated pulmonary arterial hypertension (CTD-PAH).

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 30, 2020

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NEWS #PharmaBuzz

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https://endpts.com/reata-culls-bardoxolone-ending-decade-of-rd-on-troubled-kidney-disease-drug/

Kyle LaHucik ENDPTS
11 May 2023
Reata, Kyowa Kirin ax bardoxolone, ending 13-year saga
Reata, Kyowa Kirin ax bardoxolone, ending 13-year saga

10 May 2023

// Max Bayer FIERCE BIOTECH

https://www.fiercebiotech.com/biotech/reata-kyowa-kirin-partnered-med-bardoxolone-faces-music-after-ph-3-flop-ending-13-year-saga

Max Bayer FIERCE BIOTECH
10 May 2023

https://www.businesswire.com/news/home/20220801005262/en

BUSINESSWIRE
01 Aug 2022
Reata slips as FDA rejects kidney disease therapy
Reata slips as FDA rejects kidney disease therapy

26 Feb 2022

// D. Lokuwithana SEEKING ALPHA

https://seekingalpha.com/news/3806235-reta-stock-slips-as-fda-rejects-kidney-disease-drug

D. Lokuwithana SEEKING ALPHA
26 Feb 2022

https://endpts.com/fda-slams-reatas-kidney-drug-as-ineffective-ahead-of-adcomm-meeting-wednesday/

Zachary Brennan ENDPTS
06 Dec 2021

https://www.globenewswire.com/fr/news-release/2021/03/01/2184047/0/en/Reata-Pharmaceuticals-Inc-Submits-NDA-for-Company-s-Lead-Program-Bardoxolone-in-Alport-Syndrome.html#:~:text=(Nasdaq%3A%20RETA)%20(%E2%80%9C,U.S.%20Food%20and%20Drug%20Administration

GLOBENEWSWIRE
01 Mar 2021

ABOUT THIS PAGE

Bardoxolone (methyl) Manufacturers

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

Bardoxolone (methyl) Suppliers

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

Bardoxolone (methyl) GMP

Bardoxolone (methyl) 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 Bardoxolone (methyl) 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 Bardoxolone (methyl) GMP manufacturer or Bardoxolone (methyl) GMP API supplier for your needs.

Bardoxolone (methyl) CoA

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

Bardoxolone (methyl) CoA mostly includes findings from lab analyses of a specific batch. For each Bardoxolone (methyl) 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.

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