Home Other Building Blocks 218600-53-4
218600-53-4,MFCD11983137
Catalog No.:AA006YXA

218600-53-4 | Bardoxolone methyl

Pack Size
Purity
Availability
Price(USD)
Quantity
  
5mg
98%
in stock  
$43.00   $30.00
- +
25mg
98%
in stock  
$94.00   $66.00
- +
100mg
98%
in stock  
$285.00   $199.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA006YXA
Chemical Name:
Bardoxolone methyl
CAS Number:
218600-53-4
Molecular Formula:
C32H43NO4
Molecular Weight:
505.6881
MDL Number:
MFCD11983137
SMILES:
N#CC1=C[C@@]2(C)[C@H](C(C1=O)(C)C)CC[C@@]1(C2=CC(=O)C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)OC)C
NSC Number:
713200
Properties
Computed Properties
 
Complexity:
1210  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Heavy Atom Count:
37  
Hydrogen Bond Acceptor Count:
5  
Rotatable Bond Count:
2  
XLogP3:
6.7  

Literature

Title: Characterization of the Potent, Selective Nrf2 Activator, 3-(Pyridin-3-Ylsulfonyl)-5-(Trifluoromethyl)-2H-Chromen-2-One, in Cellular and In Vivo Models of Pulmonary Oxidative Stress.

Journal: The Journal of pharmacology and experimental therapeutics 20171001

Title: High-content imaging-based BAC-GFP toxicity pathway reporters to assess chemical adversity liabilities.

Journal: Archives of toxicology 20170101

Title: Activation of Nrf2-ARE signaling mitigates cyclophosphamide-induced myelosuppression.

Journal: Toxicology letters 20161116

Title: Bardoxolone methyl modulates efflux transporter and detoxifying enzyme expression in cisplatin-induced kidney cell injury.

Journal: Toxicology letters 20160930

Title: Bardoxolone methyl prevents obesity and hypothalamic dysfunction.

Journal: Chemico-biological interactions 20160825

Title: Bardoxolone methyl prevents the development and progression of cardiac and renal pathophysiologies in mice fed a high-fat diet.

Journal: Chemico-biological interactions 20160105

Title: CDDO-Me Redirects Activation of Breast Tumor Associated Macrophages.

Journal: PloS one 20160101

Title: Bardoxolone methyl prevents fat deposition and inflammation in the visceral fat of mice fed a high-fat diet.

Journal: Chemico-biological interactions 20150305

Title: Glycogen synthase kinase 3 regulates cell death and survival signaling in tumor cells under redox stress.

Journal: Neoplasia (New York, N.Y.) 20140901

Title: Chemical tuning enhances both potency toward nrf2 and in vitro therapeutic index of triterpenoids.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20140801

Title: Immunosuppressive potential of bardoxolone methyl using a modified murine local lymph node assay (LLNA).

Journal: The Journal of toxicological sciences 20140801

Title: Bardoxolone methyl (BARD) ameliorates aristolochic acid (AA)-induced acute kidney injury through Nrf2 pathway.

Journal: Toxicology 20140406

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Bardoxolone methyl decreases megalin and activates nrf2 in the kidney.

Journal: Journal of the American Society of Nephrology : JASN 20120928

Title: Inhibition of cell proliferation and induction of apoptosis by oleanane triterpenoid (CDDO-Me) in pancreatic cancer cells is associated with the suppression of hTERT gene expression and its telomerase activity.

Journal: Biochemical and biophysical research communications 20120615

Title: Synthesis, chemical reactivity as Michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents.

Journal: Journal of medicinal chemistry 20120524

Title: Oleanolic acid.

Journal: Phytochemistry 20120501

Title: The triterpenoid CDDO-Me promotes hematopoietic progenitor expansion and myelopoiesis in mice.

Journal: Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation 20120301

Title: New hope or drawbacks: will chronic kidney disease be treatable with small molecules in the near future?

Journal: Future medicinal chemistry 20120301

Title: Deal watch: Abbott boosts investment in NRF2 activators for reducing oxidative stress.

Journal: Nature reviews. Drug discovery 20120201

Title: Oleanane triterpenoid CDDO-Me inhibits Akt activity without affecting PDK1 kinase or PP2A phosphatase activity in cancer cells.

Journal: Biochemical and biophysical research communications 20120106

Title: CDDO-methyl ester delays breast cancer development in BRCA1-mutated mice.

Journal: Cancer prevention research (Philadelphia, Pa.) 20120101

Title: Electrophilic PPARγ ligands inhibit corneal fibroblast to myofibroblast differentiation in vitro: a potentially novel therapy for corneal scarring.

Journal: Experimental eye research 20120101

Title: [Chronic kidney disease, new therapeutic approaches].

Journal: La Revue du praticien 20120101

Title: Prospective safety study of bardoxolone methyl in patients with type 2 diabetes mellitus, end-stage renal disease and peritoneal dialysis.

Journal: Contributions to nephrology 20120101

Title: Cardiac and renal function in patients with type 2 diabetes who have chronic kidney disease: potential effects of bardoxolone methyl.

Journal: Drug design, development and therapy 20120101

Title: Inhibition of cell proliferation and induction of apoptosis by CDDO-Me in pancreatic cancer cells is ROS-dependent.

Journal: Journal of experimental therapeutics & oncology 20120101

Title: Synthetic oleanane triterpenoid, CDDO-Me, induces apoptosis in ovarian cancer cells by inhibiting prosurvival AKT/NF-κB/mTOR signaling.

Journal: Anticancer research 20111101

Title: Bardoxolone: augmenting the Yin in chronic kidney disease.

Journal: Diabetes & vascular disease research 20111001

Title: Protection against 2-chloroethyl ethyl sulfide (CEES)-induced cytotoxicity in human keratinocytes by an inducer of the glutathione detoxification pathway.

Journal: Toxicology and applied pharmacology 20110901

Title: Diabetes: bardoxolone improves kidney function in type 2 diabetes.

Journal: Nature reviews. Nephrology 20110823

Title: Bardoxolone methyl and kidney function in CKD with type 2 diabetes.

Journal: The New England journal of medicine 20110728

Title: Nrf2 has a protective role against neuronal and capillary degeneration in retinal ischemia-reperfusion injury.

Journal: Free radical biology & medicine 20110701

Title: Bardoxolone methyl (BARD) ameliorates ischemic AKI and increases expression of protective genes Nrf2, PPARγ, and HO-1.

Journal: American journal of physiology. Renal physiology 20110501

Title: Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.

Journal: Journal of medicinal chemistry 20110324

Title: Effect of bardoxolone methyl on kidney function in patients with T2D and Stage 3b-4 CKD.

Journal: American journal of nephrology 20110101

Title: Role of reactive oxygen species (ROS) in CDDO-Me-mediated growth inhibition and apoptosis in colorectal cancer cells.

Journal: Journal of experimental therapeutics & oncology 20110101

Title: Bardoxolone methyl: a targeted antioxidant.

Journal: Renal failure 20110101

Title: The triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic-acid methyl ester has potent anti-diabetic effects in diet-induced diabetic mice and Lepr(db/db) mice.

Journal: The Journal of biological chemistry 20101224

Title: Synthetic triterpenoids prolong survival in a transgenic mouse model of pancreatic cancer.

Journal: Cancer prevention research (Philadelphia, Pa.) 20101101

Title: Synthetic triterpenoids target the Arp2/3 complex and inhibit branched actin polymerization.

Journal: The Journal of biological chemistry 20100903

Title: Blockage of Stat3 with CDDO-Me inhibits tumor cell growth in chordoma.

Journal: Spine 20100815

Title: Activation of signal transducer and activator of transcription 3 (Stat3) pathway in osteosarcoma cells and overexpression of phosphorylated-Stat3 correlates with poor prognosis.

Journal: Journal of orthopaedic research : official publication of the Orthopaedic Research Society 20100701

Title: Combining the FLT3 inhibitor PKC412 and the triterpenoid CDDO-Me synergistically induces apoptosis in acute myeloid leukemia with the internal tandem duplication mutation.

Journal: Molecular cancer research : MCR 20100701

Title: The synthetic triterpenoid, CDDO-Me, modulates the proinflammatory response to in vivo lipopolysaccharide challenge.

Journal: Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research 20100701

Title: CDDO-Me protects against space radiation-induced transformation of human colon epithelial cells.

Journal: Radiation research 20100701

Title: The triterpenoid CDDO-Me delays murine acute graft-versus-host disease with the preservation of graft-versus-tumor effects after allogeneic bone marrow transplantation.

Journal: Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation 20100601

Title: Fatty acid synthesis is a therapeutic target in human liposarcoma.

Journal: International journal of oncology 20100501

Title: Anti-inflammatory triterpenoid blocks immune suppressive function of MDSCs and improves immune response in cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100315

Title: Synthetic triterpenoids inhibit growth, induce apoptosis and suppress pro-survival Akt, mTOR and NF-{kappa}B signaling proteins in colorectal cancer cells.

Journal: Anticancer research 20100301

Title: Oleanane triterpenoid CDDO-Me inhibits growth and induces apoptosis in prostate cancer cells through a ROS-dependent mechanism.

Journal: Biochemical pharmacology 20100201

Title: Oleanane triterpenoid CDDO-Me induces apoptosis in multidrug resistant osteosarcoma cells through inhibition of Stat3 pathway.

Journal: BMC cancer 20100101

Title: Inhibition of nuclear factor-kappa B differentially affects thyroid cancer cell growth, apoptosis, and invasion.

Journal: Molecular cancer 20100101

Title: Triterpenoids CDDO-methyl ester or CDDO-ethyl amide and rexinoids LG100268 or NRX194204 for prevention and treatment of lung cancer in mice.

Journal: Cancer prevention research (Philadelphia, Pa.) 20091201

Title: Oleanane triterpenoid CDDO-Me inhibits growth and induces apoptosis in prostate cancer cells by independently targeting pro-survival Akt and mTOR.

Journal: The Prostate 20090601

Title: CDDO-Me, a synthetic triterpenoid, inhibits expression of IL-6 and Stat3 phosphorylation in multi-drug resistant ovarian cancer cells.

Journal: Cancer chemotherapy and pharmacology 20090301

Title: Coordinate regulation of enzyme markers for inflammation and for protection against oxidants and electrophiles.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20081014

Title: Coupling of endoplasmic reticulum stress to CDDO-Me-induced up-regulation of death receptor 5 via a CHOP-dependent mechanism involving JNK activation.

Journal: Cancer research 20080915

Title: Prevention and treatment of experimental estrogen receptor-negative mammary carcinogenesis by the synthetic triterpenoid CDDO-methyl Ester and the rexinoid LG100268.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080715

Title: Synthetic triterpenoids have cytotoxicity in pediatric acute lymphoblastic leukemia cell lines but cytotoxicity is independent of induced ceramide increase in MOLT-4 cells.

Journal: Leukemia 20080601

Title: Inhibition of mitochondrial metabolism by methyl-2-cyano-3,12-dioxooleana-1,9-diene-28-oate induces apoptotic or autophagic cell death in chronic myeloid leukemia cells.

Journal: Molecular cancer therapeutics 20080501

Title: Triterpenoid CDDO-methyl ester inhibits the Janus-activated kinase-1 (JAK1)-->signal transducer and activator of transcription-3 (STAT3) pathway by direct inhibition of JAK1 and STAT3.

Journal: Cancer research 20080415

Title: The synthetic triterpenoid CDDO-methyl ester modulates microglial activities, inhibits TNF production, and provides dopaminergic neuroprotection.

Journal: Journal of neuroinflammation 20080101

Title: Immunomodulatory activity of synthetic triterpenoids: inhibition of lymphocyte proliferation, cell-mediated cytotoxicity, and cytokine gene expression through suppression of NF-kappaB.

Journal: Immunopharmacology and immunotoxicology 20080101

Title: The synthetic oleanane triterpenoid, CDDO-methyl ester, is a potent antiangiogenic agent.

Journal: Molecular cancer therapeutics 20071201

Title: PPARgamma-active triterpenoid CDDO enhances ATRA-induced differentiation in APL.

Journal: Cancer biology & therapy 20071201

Title: Preclinical evaluation of targeting the Nrf2 pathway by triterpenoids (CDDO-Im and CDDO-Me) for protection from LPS-induced inflammatory response and reactive oxygen species in human peripheral blood mononuclear cells and neutrophils.

Journal: Antioxidants & redox signaling 20071101

Title: c-FLIP downregulation contributes to apoptosis induction by the novel synthetic triterpenoid methyl-2-cyano-3, 12-dioxooleana-1, 9-dien-28-oate (CDDO-Me) in human lung cancer cells.

Journal: Cancer biology & therapy 20071001

Title: Synthetic triterpenoids inhibit growth and induce apoptosis in human glioblastoma and neuroblastoma cells through inhibition of prosurvival Akt, NF-kappaB and Notch1 signaling.

Journal: Journal of neuro-oncology 20070901

Title: The novel triterpenoid C-28 methyl ester of 2-cyano-3, 12-dioxoolen-1, 9-dien-28-oic acid inhibits metastatic murine breast tumor growth through inactivation of STAT3 signaling.

Journal: Cancer research 20070501

Title: The synthetic triterpenoids CDDO-methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice.

Journal: Cancer research 20070315

Title: CDDO-me induces apoptosis and inhibits Akt, mTOR and NF-kappaB signaling proteins in prostate cancer cells.

Journal: Anticancer research 20070101

Title: Triterpenoid CDDO-Me blocks the NF-kappaB pathway by direct inhibition of IKKbeta on Cys-179.

Journal: The Journal of biological chemistry 20061124

Title: Depletion of intracellular glutathione contributes to JNK-mediated death receptor 5 upregulation and apoptosis induction by the novel synthetic triterpenoid methyl-2-cyano-3, 12-dioxooleana-1, 9-dien-28-oate (CDDO-Me).

Journal: Cancer biology & therapy 20060501

Title: A synthetic triterpenoid, CDDO-Me, inhibits IkappaBalpha kinase and enhances apoptosis induced by TNF and chemotherapeutic agents through down-regulation of expression of nuclear factor kappaB-regulated gene products in human leukemic cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060315

Title: The novel triterpenoid CDDO-Me suppresses MAPK pathways and promotes p38 activation in acute myeloid leukemia cells.

Journal: Leukemia 20050801

Title: c-Jun NH2-terminal kinase-mediated up-regulation of death receptor 5 contributes to induction of apoptosis by the novel synthetic triterpenoid methyl-2-cyano-3,12-dioxooleana-1, 9-dien-28-oate in human lung cancer cells.

Journal: Cancer research 20041015

Title: 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.

Journal: Journal of medicinal chemistry 20040923

Title: Synthetic triterpenoids activate a pathway for apoptosis in AML cells involving downregulation of FLIP and sensitization to TRAIL.

Journal: Leukemia 20031101

Title: A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.

Journal: Bioorganic & medicinal chemistry letters 20020408

Title: Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia.

Journal: Blood 20020101

Title: Identification of a novel synthetic triterpenoid, methyl-2-cyano-3,12-dioxooleana-1,9-dien-28-oate, that potently induces caspase-mediated apoptosis in human lung cancer cells.

Journal: Molecular cancer therapeutics 20020101

Title: 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.

Journal: Molecular endocrinology (Baltimore, Md.) 20001001

Title: Reisman SA, et al. Bardoxolone Methyl Decreases Megalin and Activates Nrf2 in the Kidney. J Am Soc Nephrol. 2012 Aug 2.

Title: McCullough PA, et al. Cardiac and renal function in patients with type 2 diabetes who have chronic kidney disease: potential effects of bardoxolone methyl. Drug Des Devel Ther. 2012;6:141-9.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Related Products of 218600-53-4
Tags:218600-53-4 Molecular Formula|218600-53-4 MDL|218600-53-4 SMILES|218600-53-4 Bardoxolone methyl