Bardoxolone methyl
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202530

CAS#: 218600-53-4

Description: Bardoxolone methyl (also known as “RTA 402” and “CDDO-methyl ester”) is an orally-available first-in-class synthetic triterpenoid belonging to the antioxidant inflammation modulator (AIM) class. It is the most potent known inducer of the Nrf2 pathway to enter clinical development and works to suppress both oxidative stress and inflammation. Bardoxolone methyl is currently being developed by Reata Pharmaceuticals, Inc. in partnership with Abbott Laboratories and Kyowa Hakko Kirin, for the treatment of advanced chronic kidney disease (CKD) in type 2 diabetes mellitus patients.


Price and Availability

Size
Price

50mg
USD 90
500mg
USD 450
5g
USD 2450
Size
Price

100mg
USD 150
1g
USD 850
10g
USD 3950
Size
Price

200mg
USD 250
2g
USD 1450
20g
USD 7450

Bardoxolone methyl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 202530
Name: Bardoxolone methyl
CAS#: 218600-53-4
Chemical Formula: C32H43NO4
Exact Mass: 505.31921
Molecular Weight: 505.69
Elemental Analysis: C, 76.00; H, 8.57; N, 2.77; O, 12.66


Synonym: Bardoxolone methyl; CDDO Methyl ester; CDDOMe; NSC 713200; RTA 402; RTA-402; RTA402.

IUPAC/Chemical Name: (4aS,6aR,6bS,12aS,14aR,14bR)-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

InChi Key: WPTTVJLTNAWYAO-OROHISIGSA-N

InChi Code: 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+/m1/s1

SMILES Code: O=C([C@]1(CC[C@@]2(C)[C@]3(C)CCC4C(C)(C)C(C(C#N)=C[C@]4(C)C3=C5)=O)CCC(C)(C)C[C@]1([H])[C@@]2([H])C5=O)OC


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Bardoxolone methyl, previously known as RTA 402, is the lead molecule emerging from ReataÂ’s platform of Antioxidant Inflammation Modulators (AIMs). The AIMs are the most potent known inducers of Nrf2, an important emerging biological target that controls the production of many of the bodyÂ’s antioxidant and detoxification enzymes. There is a strong biological rationale for the use of agents targeting Nrf2 to treat renal and cardiovascular disease. Chronic oxidative stress-mediated inflammation is known to play an important role in the degeneration of kidney function. Based on data from three clinical studies demonstrating improvements in patientsÂ’ markers of kidney function and potential disease-modifying activity, bardoxolone has been advanced to late-stage clinical development and is currently undergoing a pivotal Phase 2b trial in chronic kidney disease patients with type 2 diabetes mellitus.
 
 


References

1: Chen T, Mou Y, Tan J, Wei L, Qiao Y, Wei T, Xiang P, Peng S, Zhang Y, Huang Z, Ji H. The protective effect of CDDO-Me on lipopolysaccharide-induced acute lung injury in mice. Int Immunopharmacol. 2015 Jan 19;25(1):55-64. doi: 10.1016/j.intimp.2015.01.011. [Epub ahead of print] PubMed PMID: 25614226.

2: El-Ashmawy M, Delgado O, Cardentey A, Wright WE, Shay JW. CDDO-Me Protects Normal Lung and Breast Epithelial Cells but Not Cancer Cells from Radiation. PLoS One. 2014 Dec 23;9(12):e115600. doi: 10.1371/journal.pone.0115600. eCollection 2014. PubMed PMID: 25536195; PubMed Central PMCID: PMC4275221.

3: Wang YY, Yang YX, Zhe H, He ZX, Zhou SF. Bardoxolone methyl (CDDO-Me) as a therapeutic agent: an update on its pharmacokinetic and pharmacodynamic properties. Drug Des Devel Ther. 2014 Oct 23;8:2075-88. doi: 10.2147/DDDT.S68872. eCollection 2014. PubMed PMID: 25364233; PubMed Central PMCID: PMC4211867.

4: Deeb D, Brigolin C, Gao X, Liu Y, Pindolia KR, Gautam SC. Induction of Apoptosis in Pancreatic Cancer Cells by CDDO-Me Involves Repression of Telomerase through Epigenetic Pathways. J Carcinog Mutagen. 2014 May 31;5:177. PubMed PMID: 25152840; PubMed Central PMCID: PMC4139055.

5: Velez J, Enciso LJ, Suarez M, Fiegl M, Grismaldo A, López C, Barreto A, Cardozo C, Palacios P, Morales L, Duque JE, Carmona JU, Konopleva M, Andreeff M, Samudio I. Platelets promote mitochondrial uncoupling and resistance to apoptosis in leukemia cells: a novel paradigm for the bone marrow microenvironment. Cancer Microenviron. 2014 Aug;7(1-2):79-90. doi: 10.1007/s12307-014-0149-3. Epub 2014 Aug 12. PubMed PMID: 25112275; PubMed Central PMCID: PMC4150878.

6: Noel S, Zheng L, Navas-Acien A, Fuchs RJ. The effect of ex vivo CDDO-Me activation on nuclear factor erythroid 2-related factor 2 pathway in white blood cells from patients with septic shock. Shock. 2014 Nov;42(5):392-9. doi: 10.1097/SHK.0000000000000236. PubMed PMID: 25105464.

7: Kitsukawa M, Tsuchiyama H, Maeda A, Oshida K, Miyamoto Y. Immunosuppressive potential of bardoxolone methyl using a modified murine local lymph node assay (LLNA). J Toxicol Sci. 2014 Aug;39(4):545-50. PubMed PMID: 25056779.

8: Wu T, Ye Y, Min SY, Zhu J, Khobahy E, Zhou J, Yan M, Hemachandran S, Pathak S, Zhou XJ, Andreeff M, Mohan C. Prevention of murine lupus nephritis by targeting multiple signaling axes and oxidative stress using a synthetic triterpenoid. Arthritis Rheumatol. 2014 Nov;66(11):3129-39. doi: 10.1002/art.38782. PubMed PMID: 25047252.

9: Walsh J, Jenkins RE, Wong M, Olayanju A, Powell H, Copple I, O'Neill PM, Goldring CE, Kitteringham NR, Park BK. Identification and quantification of the basal and inducible Nrf2-dependent proteomes in mouse liver: biochemical, pharmacological and toxicological implications. J Proteomics. 2014 Aug 28;108:171-87. doi: 10.1016/j.jprot.2014.05.007. Epub 2014 May 21. PubMed PMID: 24859727; PubMed Central PMCID: PMC4115266.

10: Choi SH, Kim BG, Robinson J, Fink S, Yan M, Sporn MB, Markowitz SD, Letterio JJ. Synthetic triterpenoid induces 15-PGDH expression and suppresses inflammation-driven colon carcinogenesis. J Clin Invest. 2014 Jun;124(6):2472-82. doi: 10.1172/JCI69672. Epub 2014 May 16. PubMed PMID: 24837432; PubMed Central PMCID: PMC4089461.