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基本情報
- CAS
218600-53-4- 標準SMILES
COC(=O)[C@]12CCC(C)(C)C[C@H]1[C@H]1C(=O)C=C3[C@@]4(C)C=C(C#N)C(=O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2- InChIKey
WPTTVJLTNAWYAO-KPOXMGGZSA-N- 分子式
- C32H43NO4
- 平均分子量
- 505.7 g/mol
- 単同位体質量
- 505.31920885
名称と識別子
- 優先名称
- Bardoxolone Methyl
- IUPAC
- 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
- 現地名
- バルドキソロンメチル
- 英語名
- Bardoxolone methyl
- 分子式
- C32H43NO4
- 分子量
- 505.69
名称と別名
Bardoxolone methyl218600-53-4CDDO-MeCDDO methyl esterCDDO-Methyl esterRTA 402RTA402RTA-402NSC 713200NSC713200CEG1Q6OGU1methyl (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
名称をさらに表示
バルドキソロンメチルバルドキソロンメチル (JAN)2-シアノ-3,12-ジオキソ-28-ノルオレアナ-1,9(11)-ジエン-17-カルボン酸メチルメチル (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-シアノ-2,2,6a,6b,9,9,12a-ヘプタメチル-10,14-ジオキソ-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-オクタデカヒドロピセン-4a-カルボキシラート2-シアノ-3,12-ジオキソオレアナ-1,9(11)-ジエン-28-酸メチル3,12-ジオキソ-2-シアノオレアナ-1,9(11)-ジエン-28-酸メチルTP-155CS-322TP-155CMethylCDDOMethyl-CDDO
Bardoxolone methyl esterDTXSID5048764NSC-7132002-cyano-3,12-dioxoolean-1,9-dien-28-oic acid methyl estermethyl 2-cyano-3,12-dioxoolean-1,9-dien-28-oateDTXCID2028690(+)-methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oateMETHYL (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
物性
構造計算による物性補完中
- XLogP
- 6.7
- 極性表面積
- 84.2 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 5
- 回転可能結合数
- 2
- 重原子数
- 37
- 形式電荷
- 0
- 複雑度
- 1,210
物理化学的性質
- 融点
- 215 · 215-223°C
- 沸点
- 600.8 · 600.8±55.0 °C(Predicted)
- 比重(密度)
- 1.15 · 1.15
- 貯蔵温度
- Refrigerator
- 溶解性
- クロロホルム（微量）、メタノール（微量）
- 外見
- 個体
- 色
- 白から薄茶色
- 主な用途
- メタボロミクスビタミン、栄養補助食品、天然製品
- InChIKey
- WPTTVJLTNAWYAO-KPOXMGGZSA-N
- SMILES
- C1(=O)[C@@]([C@]2([C@](C)(C=C1C#N)C1[C@@]([C@]3([C@@](C(=O)C=1)([H])[C@]1([C@@](CC[C@](C1)(C)C)(C(OC)=O)CC3)[H])C)(C)CC2)[H])(C)C
- CAS データベース
- 218600 · 218600-53-4
化学的性質
化学的特性White to Off-White Solid
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Warning
H371 (50%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]
P260, P264, P270, P308+P316, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 1 of 2 reports by companies.；There is 1 notification provided by 1 of 2 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
安全データ
- wgk
- WGK 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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.
応用分野
説明Bardoxolone methyl is an antioxidant inflammatory modulator that reversibly interacts with critical free thiol groups of cysteine residues on KEAP-1 and other target proteins, inducing the trans-location of Nrf-2 to the nucleus and the activation of several genes, including glutathione S-transferase, haeme oxygenase, and other components of the cytoprotective response (Thomas et al., 2012). At high doses, bardoxolone methyl may also interact with other proteins, including PPAR-gamma, tubulin, and the kinase activa-tor IKK.
使用Bardoxolone methyl is an antiinflam-matory drug that activates the Nrf2-Keap1 pathway,resulting in inhibition of the proinflammatory cytokine Nf-κB.Bardoxolone methyl (BARD, CDDO-ME, RTA-402) is an orally bioavailable semi-synthetic triterpenoid compound based of the scaffold of oleanolic acid. It was developed by Reata Pharmaceuticals as an activator of the Nrf2 antioxidant pathway. It has been tested in clinical trials for kidney disease, pulmonary hypertension, and cancer.
上流・下流製品情報
上流原料
関連反応
2 件
化合物ノート
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