Page last updated: 2024-12-08

Bardoxolone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID400010
CHEMBL ID1093059
CHEBI ID177450
SCHEMBL ID954253

Synonyms (46)

Synonym
HY-14909
bardoxolone ,
CHEBI:177450
(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
gtpl2717
218600-44-3
2-cyano-3,9-dien-28-oic acid
nsc711193
nsc-711193
bdbm50096348
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid
CHEMBL1093059
rta 401
cddo
rta-401
D09584
bardoxolone (usan/inn)
7ht68l8941 ,
bardoxolone [usan:inn]
oleana-1,9(11)-dien-28-oic acid, 2-cyano-3,12-dioxo-
(+)-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid
nsc 711193
BCP9000379
BCP0726000037
CS-0728
S6647
bardoxolone [mi]
bardoxolone [inn]
bardoxolone [who-dd]
bardoxolone [usan]
SCHEMBL954253
(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-carboxylic acid
AC-29872
J-509189
C74085
EX-A1731
rta 402; ccdo;(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
cddo(bardoxolone; rta 401)
DB12651
AKOS032960362
BCP04662
TXGZJQLMVSIZEI-UQMAOPSPSA-N
Q27074871
(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)-carboxylic acid
mfcd07772296
DTXSID001025273

Research Excerpts

Overview

Bardoxolone methyl is known to be a potent activator of this Keap1-Nrf2 pathway. It has demonstrated increases in glomerular filtration rate (GFR)

ExcerptReferenceRelevance
"Bardoxolone methyl, known to be a potent activator of this Keap1-Nrf2 pathway, has demonstrated increases in glomerular filtration rate (GFR) in several clinical studies, suggesting its therapeutic potential for kidney diseases."( [Challenges in kidney disease: therapeutic potential of bardoxolone methyl].
Yamawaki, K, 2022
)
1.69
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
cyclohexenonesAny six-membered alicyclic ketone having one double bond in the ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nitric oxide synthase, inducibleMus musculus (house mouse)IC50 (µMol)0.02300.00103.39119.6000AID1226966
Nitric oxide synthase, inducibleHomo sapiens (human)IC50 (µMol)0.00020.00022.319010.0000AID241425
Ghrelin O-acyltransferaseHomo sapiens (human)IC50 (µMol)100.00006.00007.50008.0000AID1639664; AID1802486
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nuclear factor erythroid 2-related factor 2Mus musculus (house mouse)CD0.00230.00090.12580.3000AID1226965
NAD(P)H dehydrogenase [quinone] 1Mus musculus (house mouse)CD0.00270.00020.23892.6500AID589398; AID591193
Kelch-like ECH-associated protein 1Mus musculus (house mouse)CD0.00230.00090.06770.2000AID1226965
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (34)

Processvia Protein(s)Taxonomy
response to hypoxiaNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of leukocyte mediated cytotoxicityNitric oxide synthase, inducibleHomo sapiens (human)
innate immune response in mucosaNitric oxide synthase, inducibleHomo sapiens (human)
arginine catabolic processNitric oxide synthase, inducibleHomo sapiens (human)
superoxide metabolic processNitric oxide synthase, inducibleHomo sapiens (human)
nitric oxide biosynthetic processNitric oxide synthase, inducibleHomo sapiens (human)
circadian rhythmNitric oxide synthase, inducibleHomo sapiens (human)
response to bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of gene expressionNitric oxide synthase, inducibleHomo sapiens (human)
peptidyl-cysteine S-nitrosylationNitric oxide synthase, inducibleHomo sapiens (human)
prostaglandin secretionNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of interleukin-6 productionNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of interleukin-8 productionNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cell population proliferationNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of protein catabolic processNitric oxide synthase, inducibleHomo sapiens (human)
defense response to bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cellular respirationNitric oxide synthase, inducibleHomo sapiens (human)
cell redox homeostasisNitric oxide synthase, inducibleHomo sapiens (human)
regulation of insulin secretionNitric oxide synthase, inducibleHomo sapiens (human)
defense response to Gram-negative bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of killing of cells of another organismNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to lipopolysaccharideNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to type II interferonNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to xenobiotic stimulusNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cytokine production involved in inflammatory responseNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of blood pressureNitric oxide synthase, inducibleHomo sapiens (human)
response to hormoneNitric oxide synthase, inducibleHomo sapiens (human)
nitric oxide mediated signal transductionNitric oxide synthase, inducibleHomo sapiens (human)
response to lipopolysaccharideNitric oxide synthase, inducibleHomo sapiens (human)
inflammatory responseNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of guanylate cyclase activityNitric oxide synthase, inducibleHomo sapiens (human)
peptide hormone processingGhrelin O-acyltransferaseHomo sapiens (human)
peptidyl-serine octanoylationGhrelin O-acyltransferaseHomo sapiens (human)
lipid modificationGhrelin O-acyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
nitric-oxide synthase activityNitric oxide synthase, inducibleHomo sapiens (human)
protein bindingNitric oxide synthase, inducibleHomo sapiens (human)
calmodulin bindingNitric oxide synthase, inducibleHomo sapiens (human)
FMN bindingNitric oxide synthase, inducibleHomo sapiens (human)
heme bindingNitric oxide synthase, inducibleHomo sapiens (human)
tetrahydrobiopterin bindingNitric oxide synthase, inducibleHomo sapiens (human)
arginine bindingNitric oxide synthase, inducibleHomo sapiens (human)
protein homodimerization activityNitric oxide synthase, inducibleHomo sapiens (human)
metal ion bindingNitric oxide synthase, inducibleHomo sapiens (human)
flavin adenine dinucleotide bindingNitric oxide synthase, inducibleHomo sapiens (human)
NADP bindingNitric oxide synthase, inducibleHomo sapiens (human)
O-acyltransferase activityGhrelin O-acyltransferaseHomo sapiens (human)
acyltransferase activity, transferring groups other than amino-acyl groupsGhrelin O-acyltransferaseHomo sapiens (human)
serine O-acyltransferase activityGhrelin O-acyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
nucleusNitric oxide synthase, inducibleHomo sapiens (human)
nucleoplasmNitric oxide synthase, inducibleHomo sapiens (human)
cytoplasmNitric oxide synthase, inducibleHomo sapiens (human)
peroxisomeNitric oxide synthase, inducibleHomo sapiens (human)
peroxisomal matrixNitric oxide synthase, inducibleHomo sapiens (human)
cytosolNitric oxide synthase, inducibleHomo sapiens (human)
cortical cytoskeletonNitric oxide synthase, inducibleHomo sapiens (human)
perinuclear region of cytoplasmNitric oxide synthase, inducibleHomo sapiens (human)
plasma membraneNitric oxide synthase, inducibleHomo sapiens (human)
nucleusNitric oxide synthase, inducibleHomo sapiens (human)
cytosolNitric oxide synthase, inducibleHomo sapiens (human)
nucleoplasmNuclear factor erythroid 2-related factor 2Mus musculus (house mouse)
cytoplasmNuclear factor erythroid 2-related factor 2Mus musculus (house mouse)
cytosolNuclear factor erythroid 2-related factor 2Mus musculus (house mouse)
endoplasmic reticulumGhrelin O-acyltransferaseHomo sapiens (human)
endoplasmic reticulum membraneGhrelin O-acyltransferaseHomo sapiens (human)
endoplasmic reticulum membraneGhrelin O-acyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (43)

Assay IDTitleYearJournalArticle
AID1728759Anti-necroptotic activity in human HT-29 cells assessed as inhibition of TNFalpha/SM-164/Z-VAD-fmk (TSZ)-induced necroptosis by measuring cell viability at 10 uM preincubated for 30 mins followed by TSZ stimulation and measured after 16 hrs by celltiter-g2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID224261Compound was evaluated for inhibitory activity against production of nitric oxide (NO) induced by interferon-gamma (IFN-gamma) in mouse macrophages at a concentration of 0.1-1 uM1998Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19
Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages.
AID224272Inhibitory activity against nitric oxide production induced by interferon-gamma (IFN-gamma) in mouse macrophages2002Journal of medicinal chemistry, Oct-24, Volume: 45, Issue:22
Design and synthesis of tricyclic compounds with enone functionalities in rings A and C: a novel class of highly active inhibitors of nitric oxide production in mouse macrophages.
AID248346Inhibitory concentration against proliferation of MCF-7 (ER Positive) breast cancer cells2004Journal of medicinal chemistry, Sep-23, Volume: 47, Issue:20
Design, synthesis, and biological evaluation of biotin conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid for the isolation of the protein targets.
AID589412Cytotoxicity against CD-1 mouse macrophages at 10 uM2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.
AID589397Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of IFN-gamma induced NO production after 24 hrs by Griess reaction2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.
AID1728761Anti-necroptotic activity in human HT-29 cells assessed as inhibition of TNFalpha/SM-164/Z-VAD-fmk (TSZ)-induced necroptosis by measuring reduction in plasma membrane rupture at 5 uM preincubated for 30 mins followed by TSZ stimulation and measured after 2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1728762Anti-necroptotic activity in human HT-29 cells assessed as inhibition of TNFalpha/SM-164/Z-VAD-fmk (TSZ)-induced necroptosis by measuring increase in cell viability measured after 12 hrs by celltiter-glo luminescent cell viability assay2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1728767Anti-necroptotic activity in mouse L929 cells assessed as inhibition of TNFalpha/Z-VAD-fmk (TZ)-induced necroptosis by measuring increase in cell viability measured after 12 hrs by celltiter-glo luminescent cell viability assay2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID473468Drug uptake in CD1 mouse plasma at 2 umol, ip after 6 hrs by HPLC/MS2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID281330Induction of HO1 in CD1 mouse stomach at 1 umol, po after 6 hrs2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: highly potent anti-inflammatory and cytoprotective agents.
AID589396Antiinflammatory activity in CD-1 mouse Macrophage assessed as inhibition of IFN-gamma induced NO production after 48 hrs by Griess reaction2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.
AID473465Drug level in CD1 mouse liver at 2 umol, ip after 6 hrs by HPLC/MS2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID473466Drug level in CD1 mouse lung at 2 umol, ip after 6 hrs by HPLC/MS2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID132692Inhibitory activity against production of nitric oxide induced by interferon-gamma in mouse macrophages1999Bioorganic & medicinal chemistry letters, Dec-20, Volume: 9, Issue:24
Novel synthetic oleanane triterpenoids: a series of highly active inhibitors of nitric oxide production in mouse macrophages.
AID241425Inhibition of inducible nitric oxide synthase in activated macrophages2005Bioorganic & medicinal chemistry letters, May-02, Volume: 15, Issue:9
Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action.
AID591193Induction of NQO1 activity in mouse Hepa-1c1c7 cells assessed as concentration require to double the specific enzyme activity after 48 hrs2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID276830Inhibition of nitric oxide production in IFN-gamma stimulated RAW 264.7 cells2006Bioorganic & medicinal chemistry letters, Dec-15, Volume: 16, Issue:24
Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A.
AID473462Induction of HO1 in mouse RAW264.7 cells at 100 nM after 6 hrs by SDS-PAGE2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID676566Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of IFNgamma-stimulated NO production pretreated for 2 hrs before IFNgamma challenge measured after 24 hrs by Griess reaction2012Journal of medicinal chemistry, May-24, Volume: 55, Issue:10
Synthesis, chemical reactivity as Michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents.
AID1728764Cytotoxicity against human HT-29 cells assessed as reduction in cell viability at 10 uM by MTT assay2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1728760Anti-necroptotic activity in human HT-29 cells assessed as inhibition of TNFalpha/SM-164/Z-VAD-fmk (TSZ)-induced necroptosis by measuring reduction in cell swelling at 5 uM preincubated for 30 mins followed by TSZ stimulation and measured after 12 hrs by 2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1651209Induction of Nrf2 nuclear translocation in human spinal cord astrocytes relative to control2020Bioorganic & medicinal chemistry letters, 02-15, Volume: 30, Issue:4
Design, synthesis and identification of novel, orally bioavailable non-covalent Nrf2 activators.
AID281328Inhibition of interferon gamma-stimulated NO production in RAW 264.7 cells after 24 hrs2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: highly potent anti-inflammatory and cytoprotective agents.
AID1226965Activation of Keap1/Nrf2/ARE pathway in mouse Hepa-1c1c7 cells assessed as double induction of NQO1 specific activity after 48 hrs by bicinchoninic acid assay2015Journal of medicinal chemistry, Jun-11, Volume: 58, Issue:11
New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase.
AID1226966Inhibition of iNOS in LPS-stimulated mouse RAW264.7 cells assessed as inhibition of nitric oxide production after 48 hrs by Griess assay2015Journal of medicinal chemistry, Jun-11, Volume: 58, Issue:11
New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase.
AID281329Induction of HO1 in CD1 mouse liver at at 1 umol, po after 6 hrs2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: highly potent anti-inflammatory and cytoprotective agents.
AID1728766Protection against TNFalpha/cycloheximide (TC)-induced apoptosis in human HT-29 cells assessed as increase in cell viability at 0.08 to 10 uM measured after 24 hrs by celltiter-glo luminescent cell viability assay2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1728765Protection against TNFalpha/SM-164 (TS)-induced apoptosis in human HT-29 cells assessed as increase in cell viability at 0.08 to 10 uM measured after 20 hrs by celltiter-glo luminescent cell viability assay2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID589405Induction of HO-1 expression in CD-1 mouse liver at 1 umol administered via gavage measured after 6 hrs by Western blotting2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.
AID772450Antiinflammatory activity in mouse macrophages assessed as inhibition of IFN-gamma-induced nitric oxide production after 48 hrs by Griess method2013Journal of medicinal chemistry, Oct-10, Volume: 56, Issue:19
Keap calm, and carry on covalently.
AID140447Inhibitory activity against production of nitric oxide induced by interferon gamma in mouse macrophages2002Bioorganic & medicinal chemistry letters, Apr-08, Volume: 12, Issue:7
A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.
AID589406Induction of HO-1 expression in CD-1 mouse stomach at 1 umol administered via gavage measured after 6 hrs by Western blotting2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.
AID589398Induction of NQO1 activity in in mouse Hepa-1c1c7 cells after 48 hrs2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.
AID473461Antiinflammatory activity against IFN-gamma-stimulated mouse RAW264.7 cells assessed as nitrite accumulation after 24 hrs by Griess reagent method2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID1728763Anti-necroptotic activity in human HT-29 cells assessed as inhibition of TNFalpha/cycloheximide/Z-VAD-fmk (TCZ)-induced necroptosis by measuring increase in cell viability measured after 16 hrs by celltiter-glo luminescent cell viability assay2021European journal of medicinal chemistry, Feb-15, Volume: 212Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1243950Cytotoxicity against human MCF7 cells assessed as inhibition of cell proliferation after 3 days by radioactive thymidine incorporation assay2015European journal of medicinal chemistry, Aug-28, Volume: 101Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids.
AID224269Inhibition of nitric oxide (NO) production induced by interferon-gamma (IFN-gamma) in mouse macrophages2000Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22
Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages.
AID473467Drug level in CD1 mouse whole blood at 2 umol, ip after 6 hrs by HPLC/MS2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID591192Inhibition of NO production in INFgamma-stimulated mouse RAW264.7 cells measured after 24 hrs by Griess reaction method2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent.
AID1346800Human Peroxisome proliferator-activated receptor-gamma (1C. Peroxisome proliferator-activated receptors)2000Molecular endocrinology (Baltimore, Md.), Oct, Volume: 14, Issue:10
A synthetic triterpenoid, 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), is a ligand for the peroxisome proliferator-activated receptor gamma.
AID1346217Human kelch like ECH-associated protein 1 (Kelch-like proteins)2014PloS one, , Volume: 9, Issue:6
Structure of the BTB domain of Keap1 and its interaction with the triterpenoid antagonist CDDO.
AID1802486GOAT Activity Assay from Article 10.1021/acs.biochem.6b01008: \\Synthetic Triterpenoid Inhibition of Human Ghrelin O-Acyltransferase: The Involvement of a Functionally Required Cysteine Provides Mechanistic Insight into Ghrelin Acylation.\\2017Biochemistry, 02-21, Volume: 56, Issue:7
Synthetic Triterpenoid Inhibition of Human Ghrelin O-Acyltransferase: The Involvement of a Functionally Required Cysteine Provides Mechanistic Insight into Ghrelin Acylation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (64)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (3.13)18.2507
2000's8 (12.50)29.6817
2010's9 (14.06)24.3611
2020's45 (70.31)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.40

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.40 (24.57)
Research Supply Index4.19 (2.92)
Research Growth Index5.50 (4.65)
Search Engine Demand Index63.73 (26.88)
Search Engine Supply Index1.92 (0.95)

This Compound (45.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.56%)5.53%
Reviews8 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (1.56%)0.25%
Other54 (84.38%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]