Bardoxolone
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MedKoo CAT#: 329647

CAS#: 218600-44-3

Description: Bardoxolone, also known as RTA-401 and CDDO, 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.

Chemical Structure

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Bardoxolone
CAS# 218600-44-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329647
Name: Bardoxolone
CAS#: 218600-44-3
Chemical Formula: C31H41NO4
Exact Mass: 491.30
Molecular Weight: 491.670
Elemental Analysis: C, 75.73; H, 8.41; N, 2.85; O, 13.02

Price and Availability

Size Price Availability Quantity
10mg USD 110 Ready to ship
25mg USD 220 Ready to ship
50mg USD 350 Ready to ship
100mg USD 600 Ready to ship
200mg USD 950 Ready to ship
500mg USD 1650 Ready to ship
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Synonym: CDDO; RTA 401; RTA-401; RTA401; Bardoxolone

IUPAC/Chemical Name: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydropicene-4a(2H)-carboxylic acid

InChi Key: TXGZJQLMVSIZEI-UQMAOPSPSA-N

InChi Code: InChI=1S/C31H41NO4/c1-26(2)10-12-31(25(35)36)13-11-30(7)23(19(31)16-26)20(33)14-22-28(5)15-18(17-32)24(34)27(3,4)21(28)8-9-29(22,30)6/h14-15,19,21,23H,8-13,16H2,1-7H3,(H,35,36)/t19-,21-,23-,28-,29+,30+,31-/m0/s1

SMILES Code: CC(C)([C@](CC[C@@]([C@@]1(CC[C@]2(CCC(C)(C[C@]2([C@]13[H])[H])C)C(O)=O)C)4C)5[H])C(C(C#N)=C[C@]5(C)C4=CC3=O)=O

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

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).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Bardoxolone is a nuclear regulator factor (Nrf-2) activator.
In vitro activity: Bardoxolone (BARD; CDDO-methyl), a pharmacological activator of Nrf2, increased Smad7 levels and attenuated TGF-β/Smad/ECM expression in MES-13. Reference: Free Radic Biol Med. 2019 Jul;138:33-42. https://www.sciencedirect.com/science/article/abs/pii/S0891584919300589?via%3Dihub
In vivo activity: In an aristolochic acid (AA)-mediated nephropathy mouse model, the renal expression of Nrf2 and Smad7 was elevated by BARD treatment, and AA-induced tubular necrosis and interstitial fibrosis were substantially ameliorated by BARD. Reference: Free Radic Biol Med. 2019 Jul;138:33-42. https://www.sciencedirect.com/science/article/abs/pii/S0891584919300589?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.0 10.20

Preparing Stock Solutions

The following data is based on the product molecular weight 491.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Song MK, Lee JH, Ryoo IG, Lee SH, Ku SK, Kwak MK. Bardoxolone ameliorates TGF-β1-associated renal fibrosis through Nrf2/Smad7 elevation. Free Radic Biol Med. 2019 Jul;138:33-42. doi: 10.1016/j.freeradbiomed.2019.04.033. Epub 2019 May 3. PMID: 31059771.
In vitro protocol: 1. Song MK, Lee JH, Ryoo IG, Lee SH, Ku SK, Kwak MK. Bardoxolone ameliorates TGF-β1-associated renal fibrosis through Nrf2/Smad7 elevation. Free Radic Biol Med. 2019 Jul;138:33-42. doi: 10.1016/j.freeradbiomed.2019.04.033. Epub 2019 May 3. PMID: 31059771.
In vivo protocol: 1. Song MK, Lee JH, Ryoo IG, Lee SH, Ku SK, Kwak MK. Bardoxolone ameliorates TGF-β1-associated renal fibrosis through Nrf2/Smad7 elevation. Free Radic Biol Med. 2019 Jul;138:33-42. doi: 10.1016/j.freeradbiomed.2019.04.033. Epub 2019 May 3. PMID: 31059771.

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1: Hermann C, Lang S, Popp T, Hafner S, Steinritz D, Rump A, Port M, Eder S. Bardoxolone-Methyl (CDDO-Me) Impairs Tumor Growth and Induces Radiosensitization of Oral Squamous Cell Carcinoma Cells. Front Pharmacol. 2021 Jan 29;11:607580. doi: 10.3389/fphar.2020.607580. PMID: 33584286; PMCID: PMC7878525.


2: Yamazaki T, Mimura I, Tanaka T, Nangaku M. Treatment of Diabetic Kidney Disease: Current and Future. Diabetes Metab J. 2021 Jan;45(1):11-26. doi: 10.4093/dmj.2020.0217. Epub 2021 Jan 22. PMID: 33508907; PMCID: PMC7850867.


3: Pedrosa AL, Bitencourt L, Paranhos RM, Leitão CA, Ferreira GC, Simões E Silva AC. Alport Syndrome: a comprehensive review on genetics, pathophysiology, histology, clinical, and therapeutic perspectives. Curr Med Chem. 2021 Jan 7. doi: 10.2174/0929867328666210108113500. Epub ahead of print. PMID: 33423643.


4: Sakuma H, Hagiwara S, Kantharidis P, Gohda T, Suzuki Y. Potential Targeting of Renal Fibrosis in Diabetic Kidney Disease Using MicroRNAs. Front Pharmacol. 2020 Nov 13;11:587689. doi: 10.3389/fphar.2020.587689. PMID: 33364960; PMCID: PMC7751689.


5: Wang Y, Ma H, Huang J, Yao Z, Yu J, Zhang W, Zhang L, Wang Z, Zhuang C. Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors. Eur J Med Chem. 2021 Feb 15;212:113030. doi: 10.1016/j.ejmech.2020.113030. Epub 2020 Nov 21. PMID: 33248849.


6: Baran SW, Gupta AD, Lim MA, Mathur A, Rowlands DJ, Schaevitz LR, Shanmukhappa SK, Walker DB. Continuous, Automated Breathing Rate and Body Motion Monitoring of Rats With Paraquat-Induced Progressive Lung Injury. Front Physiol. 2020 Oct 16;11:569001. doi: 10.3389/fphys.2020.569001. PMID: 33178039; PMCID: PMC7596732.


7: Szczesny-Malysiak E, Stojak M, Campagna R, Grosicki M, Jamrozik M, Kaczara P, Chlopicki S. Bardoxolone Methyl Displays Detrimental Effects on Endothelial Bioenergetics, Suppresses Endothelial ET-1 Release, and Increases Endothelial Permeability in Human Microvascular Endothelium. Oxid Med Cell Longev. 2020 Oct 14;2020:4678252. doi: 10.1155/2020/4678252. PMID: 33123312; PMCID: PMC7584962.


8: Rice CA, Colon BL, Chen E, Hull MV, Kyle DE. Discovery of repurposing drug candidates for the treatment of diseases caused by pathogenic free-living amoebae. PLoS Negl Trop Dis. 2020 Sep 24;14(9):e0008353. doi: 10.1371/journal.pntd.0008353. PMID: 32970675; PMCID: PMC7546510.


9: Tong B, Luo M, Xie Y, Spradlin JN, Tallarico JA, McKenna JM, Schirle M, Maimone TJ, Nomura DK. Bardoxolone conjugation enables targeted protein degradation of BRD4. Sci Rep. 2020 Sep 23;10(1):15543. doi: 10.1038/s41598-020-72491-9. PMID: 32968148; PMCID: PMC7511954.


10: Tian TT, Li QR, Gan SQ, Chang CR, Shen XC. Protective Effect of Simplicillium sp. Ethyl Acetate Extract against High Glucose-Induced Oxidative Stress in HUVECs. Evid Based Complement Alternat Med. 2020 Aug 15;2020:5172765. doi: 10.1155/2020/5172765. PMID: 32879632; PMCID: PMC7448235.


11: Lewis JH, Jadoul M, Block GA, Chin MP, Ferguson DA, Goldsberry A, Meyer CJ, O'Grady M, Pergola PE, Reisman SA, Wigley WC, Chertow GM. Effects of Bardoxolone Methyl on Hepatic Enzymes in Patients with Type 2 Diabetes Mellitus and Stage 4 CKD. Clin Transl Sci. 2021 Jan;14(1):299-309. doi: 10.1111/cts.12868. Epub 2020 Sep 3. PMID: 32860734; PMCID: PMC7877861.


12: Rush BM, Bondi CD, Stocker SD, Barry KM, Small SA, Ong J, Jobbagy S, Stolz DB, Bastacky SI, Chartoumpekis DV, Kensler TW, Tan RJ. Genetic or pharmacologic Nrf2 activation increases proteinuria in chronic kidney disease in mice. Kidney Int. 2021 Jan;99(1):102-116. doi: 10.1016/j.kint.2020.07.036. Epub 2020 Aug 18. PMID: 32818518; PMCID: PMC7785672.


13: Meng X, Waddington JC, Tailor A, Lister A, Hamlett J, Berry N, Park BK, Sporn MB. CDDO-imidazolide Targets Multiple Amino Acid Residues on the Nrf2 Adaptor, Keap1. J Med Chem. 2020 Sep 10;63(17):9965-9976. doi: 10.1021/acs.jmedchem.0c01088. Epub 2020 Aug 19. PMID: 32787104.


14: Yagishita Y, Gatbonton-Schwager TN, McCallum ML, Kensler TW. Current Landscape of NRF2 Biomarkers in Clinical Trials. Antioxidants (Basel). 2020 Aug 7;9(8):716. doi: 10.3390/antiox9080716. PMID: 32784785; PMCID: PMC7464243.


15: Kim J, Hagen CE, Kumar SN, Park JI, Zimmerman MA, Hong JC. Anticholestatic Effect of Bardoxolone Methyl on Hepatic Ischemia-reperfusion Injury in Rats. Transplant Direct. 2020 Jul 17;6(8):e584. doi: 10.1097/TXD.0000000000001017. PMID: 32766432; PMCID: PMC7371100.


16: Cuadrado A, Pajares M, Benito C, Jiménez-Villegas J, Escoll M, Fernández- Ginés R, Garcia Yagüe AJ, Lastra D, Manda G, Rojo AI, Dinkova-Kostova AT. Can Activation of NRF2 Be a Strategy against COVID-19? Trends Pharmacol Sci. 2020 Sep;41(9):598-610. doi: 10.1016/j.tips.2020.07.003. Epub 2020 Jul 14. PMID: 32711925; PMCID: PMC7359808.


17: Kanda H, Yamawaki K. Bardoxolone methyl: drug development for diabetic kidney disease. Clin Exp Nephrol. 2020 Oct;24(10):857-864. doi: 10.1007/s10157-020-01917-5. Epub 2020 Jun 27. PMID: 32594372; PMCID: PMC7497696.


18: Harrington BS, Ozaki MK, Caminear MW, Hernandez LF, Jordan E, Kalinowski NJ, Goldlust IS, Guha R, Ferrer M, Thomas C, Shetty J, Tran B, Wong N, House CD, Annunziata CM. Drugs Targeting Tumor-Initiating Cells Prolong Survival in a Post-Surgery, Post-Chemotherapy Ovarian Cancer Relapse Model. Cancers (Basel). 2020 Jun 21;12(6):1645. doi: 10.3390/cancers12061645. PMID: 32575908; PMCID: PMC7352549.


19: Kalvala AK, Kumar R, Sherkhane B, Gundu C, Arruri VK, Kumar A. Bardoxolone Methyl Ameliorates Hyperglycemia Induced Mitochondrial Dysfunction by Activating the keap1-Nrf2-ARE Pathway in Experimental Diabetic Neuropathy. Mol Neurobiol. 2020 Aug;57(8):3616-3631. doi: 10.1007/s12035-020-01989-0. Epub 2020 Jun 19. PMID: 32556916.


20: Nangaku M, Kanda H, Takama H, Ichikawa T, Hase H, Akizawa T. Randomized Clinical Trial on the Effect of Bardoxolone Methyl on GFR in Diabetic Kidney Disease Patients (TSUBAKI Study). Kidney Int Rep. 2020 Apr 14;5(6):879-890. doi: 10.1016/j.ekir.2020.03.030. PMID: 32518870; PMCID: PMC7271944.