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.
- Molecular Weight: 505.70
- Molecular Formula: C32H43NO4
Purity: ≥ 98.0%
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
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
InChIKey: WPTTVJLTNAWYAO-FUARBKCBSA-N
- Boiling Point: 600.8°C at 760 mmHg
- Solubility: Soluble in DMSO, not in water
- Appearance: Off-white to yellow powder
- Application: Bardoxolone methyl, also known as RTA 402, is a semisynthetic derivative of oleanolic acid that has attracted much attention in the medical community for its potential to treat a variety of chronic diseases, especially chronic kidney disease (CKD). As a member of the antioxidant inflammatory modulator (AIM) class of drugs, bardoxolone methyl exerts its therapeutic effects by targeting inflammation and oxidative stress, two key pathological processes in many chronic diseases. Bardoxolone methyl primarily acts by activating the Nrf2 pathway. Nrf2, or nuclear factor erythroid 2-related factor 2, is a transcription factor that regulates the expression of antioxidant proteins, thereby protecting against oxidative damage triggered by injury and inflammation. Under normal conditions, Nrf2 binds to Keap1 (Kelch-like ECH-associated protein 1) in the cytoplasm, thereby promoting its degradation. Bardoxolone methyl disrupts this interaction, allowing Nrf2 to translocate to the nucleus, where it activates the antioxidant response element (ARE) and induces the expression of multiple cytoprotective genes. These genes play a crucial role in reducing oxidative stress and inflammation, and enhancing cellular protection and repair mechanisms.Applications in Chronic Kidney DiseaseCKD is characterized by a progressive loss of kidney function, often leading to end-stage renal disease (ESRD). Inflammation and oxidative stress are key to the pathogenesis of CKD, making bardoxolone methyl a promising therapeutic candidate. Clinical trials, such as the BEACON study, have investigated the efficacy of bardoxolone methyl in patients with CKD. The drug has shown the potential to improve estimated glomerular filtration rate (eGFR), a key measure of kidney function. By alleviating oxidative stress and reducing inflammation, bardoxolone methyl helps slow the progression of kidney damage, offering hope to patients with CKD.Applications Beyond CKDWhile the primary focus of bardoxolone methyl is on CKD, its potential therapeutic benefits extend to other diseases characterized by inflammation and oxidative stress. These include: 1. Pulmonary Arterial Hypertension (PAH): PAH is a serious, progressive disease characterized by elevated blood pressure in the pulmonary arteries. Inflammation and oxidative stress are important factors in the pathogenesis of PAH. Bardoxolone methyl has shown promise in preclinical studies and early clinical trials by modulating these pathogenic processes, potentially improving quality of life and outcomes for patients with PAH.2. Liver disease: Nonalcoholic steatohepatitis (NASH) is another disease characterized by severe inflammation and oxidative stress. The anti-inflammatory and antioxidant properties of bardoxolone methyl have been explored in this context, with studies suggesting that it may help reduce liver damage and improve metabolic health in patients with NASH.3. Neurological disease: Neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease are severely affected by oxidative stress and chronic inflammation. While research in this area is still in its early stages, bardoxolone methyl has the potential to provide therapeutic benefits by protecting neuronal cells from oxidative damage and reducing neuroinflammation.
- Storage: Store in dry, dark and ventilated place.
Synonyms:
CDDO Methyl ester; CDDOMe; RTA 402; RTA-402; RTA402; TP-155; TP155; TP 155; 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid methyl ester; bardoxolone methyl; CDDO-Me; methyl 2-cyano-3,12-dioxoolean-1,9-dien-28-oate; (4aS,6aR,6bS,8aR,12aS,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
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