Compound: Bardoxolone methyl
SMILES: O=C1C(C#N)=C[C@@]2(C3=CC(=O)[C@@H]4[C@H]5[C@](C(=O)OC)(CCC(C5)(C)C)CC[C@]4([C@]3(C)CC[C@H]2C1(C)C)C)C
InChIKey: WPTTVJLTNAWYAO-KPOXMGGZSA-N
Synonyms: Bardoxolone methyl, 218600-53-4, CDDO-Me, CDDO methyl ester, CDDO-Methyl ester, RTA 402, RTA-402, RTA402, NSC 713200, NSC713200, 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, Bardoxolone methyl ester, CEG1Q6OGU1, NSC-713200, DTXSID5048764, DTXCID2028690, methyl 2-cyano-3,12-dioxoolean-1,9-dien-28-oate, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid methyl ester, METHYL (4AS,6AR,6BS,8AR,12AS,14AR,14BS)-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, (+)-methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate, RefChem:560941, Bardoxolone methyl [USAN], 2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic Acid Methyl Ester, 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, C32H43NO4, bardoxolone-methyl, (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, TP-155, MFCD11983137, NCGC00186460-01, UNII-CEG1Q6OGU1, CDDO-Me, 2, GTPL3443, Bardoxolone methyl (JAN/USAN), BARDOXOLONE METHYL [JAN], CHEMBL1762621, SCHEMBL12521530, CHEBI:177406, WPTTVJLTNAWYAO-KPOXMGGZSA-N, 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid methyl ester, BDBM217379, BARDOXOLONE METHYL [WHO-DD], Tox21_113229, s8078, BARDOXOLONE METHYL ESTER [MI], AKOS025401880, CCG-269743, CS-0598, DB05983, EBC-219094, FB15804, CDDO Methyl Ester, >=98% (HPLC), NCGC00186460-07, AC-26830, CSA:218600-53-4;Bardoxolone methyl, HY-13324, methyl (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydropicene-4a(2H)-carboxylate, SY039275, CAS-218600-53-4, NS00069711, D09585, NSC 713200; RTA 402; CDDO Methyl ester, Q4860208, Oleana-1,9(11)-dien-28-oic acid, 2-cyano-3,12-dioxo-, methyl ester, Methyl bardoxo lonate; methyl (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydropicene-4a(2H)-carboxylate
Theoretical properties:
molecular_formula: C32H43NO4
molecular_weight: 505.7 g/mol
exact_mass: 505.31920885 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 37
topological_polar_surface_area: 84.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Bardoxolone methyl is a member of cyclohexenones.
chembl: BARDOXOLONE METHYL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Bardoxolone methyl (also known as “RTA 402”, “CDDO-methyl ester”, CDDO-Me, and more formally methyl bardoxolonate) is an experimental and orally-bioavailable semi-synthetic triterpenoid, based on the scaffold of the natural product oleanolic acid. Pre-clinical studies indicate that the compound acts as an activator of the Nrf2 pathway and an inhibitor of the NF-κB pathway. A phase 3 clinical trial evaluating bardoxolone methyl for the treatment of chronic kidney disease (CKD) was terminated in October 2012 after patients treated with the drug were found to have experienced a higher rate of heart-related adverse events, including heart failure, hospitalizations, and deaths.
An advisory committee meeting of experts voted unanimously that bardoxolone methyl was not effective in slowing the progression of chronic kidney disease in Alport syndrome and that its benefits did not outweigh its risks. A Complete Response Letter from FDA stated a similar opinion.