ChemicalBook--->CAS DataBase List--->932730-51-3

932730-51-3

932730-51-3 Structure

932730-51-3 Structure
IdentificationBack Directory
[Name]

CDDO-EA
[CAS]

932730-51-3
[Synonyms]

TP319
TP 319
RTA405
RTA-405
RTA 405
CDDO-EA
TP-319)
CS-1305
CDDO ethyl amide
Bardoxolone ethyl amide
CDDO EA, RTA 405, tP 319
CDDO-EA (CDDO ethyl amide
Oleana-1,9(11)-dien-28-amide, 2-cyano-N-ethyl-3,12-dioxo-
CDDO ETHYL AMIDE;RTA405;TP319;RTA 405;TP 319;RTA-405;TP-319
[Molecular Formula]

C33H46N2O3
[MDL Number]

MFCD11983136
[MOL File]

932730-51-3.mol
[Molecular Weight]

518.73
Chemical PropertiesBack Directory
[Boiling point ]

670.7±55.0 °C(Predicted)
[density ]

1.13±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO: ≥ 34 mg/mL (65.54 mM)
[form ]

Powder
[pka]

16.21±0.70(Predicted)
[color ]

White to off-white
Hazard InformationBack Directory
[Uses]

CDDO-EA is an NF-E2 related factor 2/antioxidant response element (Nrf2/ARE) activator.
[Biological Activity]

CDDO-EA is a NF-E2-related factor 2/antioxidant response element (Nrf2/ARE) activator.
[in vitro]

CDDO-EA potently activates Nrf2/ARE in a cell culture model of ALS and in the G93A SOD1 mouse model of ALS. CDDO-EA is a potent inducer of apoptosis in A549 lung cancer cells, as shown both by PARP cleavage and Annexin staining. It is more potent than CDDO itself as inducers of heme oxygenase-1 (HO-1). In RAW264.7 macrophage-like cells, CDDO-EA is 7-fold more potent than CDDO as suppressors of the ability of IFN-γ to induce iNOS.

[in vivo]

The survival analysis shows that G93A mice treated with CDDO-EA, compared to G93A littermate controls, lives significantly longer. CDDO-EA treatment increases the life-span by 20.6 days from 124.05±3.7 days to 144.72±8.1 days (16.6%) (p<0.001). In CDDO-EA-treated G93A mice, the age of death is 141.4±5.2 days and the duration from the age of onset to the age of death is 57.6±7.6 days, which means that the age of death from onset is prolonged by 17.5 days (43%).

[target]

Nrf2/ARE

[References]

[1] Neymotin A, et al. Neuroprotective effect of Nrf2/ARE activators, CDDO ethylamide and CDDO trifluoroethylamide, in a mouse model of amyotrophic lateral sclerosis. Free Radic Biol Med. 2011 Jul 1;51(1):88-96. DOI:10.1016/j.freeradbiomed.2011.03.027
[2] Liby K, et al. The synthetic triterpenoids CDDO-methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice. Cancer Res. 2007 Mar 15;67(6):2414-9. DOI:10.1158/0008-5472.CAN-06-4534
Spectrum DetailBack Directory
[Spectrum Detail]

CDDO-EA(932730-51-3)1HNMR
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