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Bardoxolone

HCID 400010
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
218600-44-3
Standard SMILES
CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](C(=O)C=C4[C@@]5(C)C=C(C#N)C(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1
InChIKey
TXGZJQLMVSIZEI-UQMAOPSPSA-N
Molecular formula
C31H41NO4
Average molar mass
491.7 g/mol
Monoisotopic mass
491.30355879

Names & identifiers

Preferred name
Bardoxolone
IUPAC
(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-carboxylic acid
English name
Bardoxolone
Molecular formula
C31H41NO4
Molecular weight
491.66

Names & synonyms

Bardoxolone218600-44-3CDDORTA-401RTA 4012-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid(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-carboxylic acidBardoxolonaRTA401NSC7111937HT68L8941DTXSID001025273
Show more names
CCDOCS-321RTA 401|||CDDOCDDO(Bardoxolone)Bardoxolone (CDDO)bardoxolone RTA 401
(+)-2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acidOleana-1,9(11)-dien-28-oic acid, 2-cyano-3,12-dioxo-CDDO acidbardoxolonumDTXSID50870250RefChem:5609402-cyano-3,12-dioxoolean-1,9-dien-28-oic acidDTXCID60818022

Database identifiers

CAS
218600-44-3
PubChem CID
400010
DTXSID
DTXSID001025273
ChEMBL
CHEMBL1093059
ChEBI

Properties

Computed structural propertiesFilling in

XLogP
6.4
Topological polar surface area
95.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
1
Heavy atoms
36
Formal charge
0
Complexity
1,200

Physicochemical properties

Melting point
180 · 180-182 °C
Boiling point
632.9 · 632.9±55.0 °C(Predicted)
Density
1.18 · 1.18
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
49.2 mg/mL · ≥49.2 mg/mL in DMSO; insoluble in H2O; ≥2.682 mg/mL in EtOH with gentle warming and ultrasonic
form
solid
pka
4.52 · 4.52±0.70(Predicted)
color
White to yellow
InChIKey
TXGZJQLMVSIZEI-UQMAOPSPSA-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(O)=O)CC3)[H])C)(C)CC2)[H])(C)C
NCI Dictionary of Cancer Terms
CDDO
FDA UNII
7 HT68L8941 · 7HT68L8941
Symbol(GHS)
7 · GHS07
Signal word
Warning

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P264-P270-P271-P280-P301+P312-P330-P302+P352-P321-P304+P340-P305+P351+P338-P332+P313-P362+P364-P337+P313-P403+P233-P405-P501

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Bardoxolone, a synthetic triterpenoid, is a highly potent activator of redox-sensitive signaling pathways that induce programmed cell death (apoptosis) in cancer cells that are under high levels of intrinsic oxidative stress. In contrast, Bardoxolone in normal cells induces protective antioxidant/anti-inflammatory responses. Intensive research in animal models of human cancer has demonstrated that Bardoxolone is a potent anticancer agent with a well-characterized ability to inhibit growth and cause regression of tumors as a single agent and in combination with radiation and chemotherapy. Bardoxolone also suppresses radiation- and chemotherapy-induced damage (e.g., oral mucositis) in normal tissues at dose levels that also produce an anti-cancer effect. Bardoxolone induces apoptosis through both caspase-independent and -dependent mechanisms, the latter involving caspase-8 activation, Bid cleavage, cytochrome c release, and caspase-3 activation. Furthermore, JNK, p38, and ERK pathways are involved in Bardoxolone-induced apoptosis of tumor cell lines mediated by disrupted intracellular redox balance and involving decreased glutathione and increased reactive oxygen species. Study shows that Bardoxolone enhances p42 CEBPA protein at the level of translation.

Applications · 1 item

UsesBardoxolone is a synthetic oleanane triterpenoid that exerts multifunctional activities in the control of cellular growth and differentiation. Bardoxolone is capable of activating the transcription fa ctor peroxisome proliferator activator receptor-γ (PPARγ), its apoptotic effects in malignant cells have been shown to occur independently of PPARγ. Bardoxolone was developed as an potential drug for the improvement of hyperglycemia, proteinuria, glomerulus structure, serum creatine, which may in turn be beneficial to treat diabetic kidney diseases, cancer and thromboembolic events.

Upstream & downstream products

Upstream raw materials

(4aS,6aR,6bS,12aS,14aR,14bR,Z)-Methyl 11-(hydroxyMethylene)-2,2,6a,6b,9,9,12a-heptaMethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate

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Related reactions

2 records
New reaction record
HRID 1713727 reaction equation
HRID 1713727As reactantuspto-grants-2010_09
HRID 2115162 reaction equation
HRID 2115162As reactantuspto-grants-2008_10

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEBI:177450
UNII
7HT68L8941
Nikkaji
J1.078.865J
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P264-P270-P271-P280-P301+P312-P330-P302+P352-P321-P304+P340-P305+P351+P338-P332+P313-P362+P364-P337+P313-P403+P233-P405-P501
(4aS,6aR,6bS,12aS,14aR,14bR)-Methyl 11-cyano-10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,14,14a,14b-octadecahydropicene-4a-carboxylate
218600-51-2
Bardoxolone methyl
(4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate
Oleanolic acid
(4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate
(4aS,6aR,6bS,13aS,15aR,15bR)-Methyl 2,2,6a,6b,9,9,13a-heptaMethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate
Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester (9CI)

Additional notes

DefinitionChEBI: Bardoxolone is a member of cyclohexenones.