Bardoxolone Methyl
Grundinformationen
- CAS
218600-53-4- Standard-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- Summenformel
- C32H43NO4
- Durchschnittliche Molmasse
- 505,7 g/mol
- Monoisotopische Masse
- 505,31920885
Namen und Bezeichner
- Bevorzugter Name
- 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
- Englischer Name
- Bardoxolone methyl
- Summenformel
- C32H43NO4
- Molmasse
- 505.69
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
218600-53-4- PubChem CID
- 400769
- DTXSID
DTXSID5048764
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,7
- Polarare Oberfläche (TPSA)
- 84,2 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 37
- Formalladung
- 0
- Komplexität
- 1.210
Physikochemische Eigenschaften
- Schmelzpunkt
- 215 · 215-223°C
- Siedepunkt
- 600.8 · 600.8±55.0 °C(Predicted)
- Dichte
- 1.15 · 1.15
- storage temp.
- Refrigerator
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- Farbe
- White to Light Brown
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- 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 Datenbank
- 218600 · 218600-53-4
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
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.
Anwendungen
BeschreibungBardoxolone 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.
VerwendenBardoxolone 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.
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