218600-53-4 | BARDOXOLONE METHYL

Packsize	Purity	Availability	Price	Discounted Price
5mg	95%	in stock	$44.00	$31.00
25mg	95%	in stock	$93.00	$65.00
100mg	95%	in stock	$232.00	$162.00
250mg	95%	in stock	$415.00	$290.00
500mg	95%	in stock	$720.00	$504.00

Description

• Catalog Number: AD25098
• 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

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

• 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.

  The Journal of pharmacology and experimental therapeutics 20171001

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

  Archives of toxicology 20170101

• Activation of Nrf2-ARE signaling mitigates cyclophosphamide-induced myelosuppression.

  Toxicology letters 20161116

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

  Toxicology letters 20160930

• Bardoxolone methyl prevents obesity and hypothalamic dysfunction.

  Chemico-biological interactions 20160825

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

  Chemico-biological interactions 20160105

• CDDO-Me Redirects Activation of Breast Tumor Associated Macrophages.

  PloS one 20160101

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

  Chemico-biological interactions 20150305

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

  Neoplasia (New York, N.Y.) 20140901

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

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

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

  The Journal of toxicological sciences 20140801

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

  Toxicology 20140406

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

  Bioorganic & medicinal chemistry letters 20130801

• Bardoxolone methyl decreases megalin and activates nrf2 in the kidney.

  Journal of the American Society of Nephrology : JASN 20120928

• 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.

  Biochemical and biophysical research communications 20120615

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

  Journal of medicinal chemistry 20120524

• Oleanolic acid.

  Phytochemistry 20120501

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

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

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

  Future medicinal chemistry 20120301

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

  Nature reviews. Drug discovery 20120201

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

  Biochemical and biophysical research communications 20120106

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

  Cancer prevention research (Philadelphia, Pa.) 20120101

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

  Experimental eye research 20120101

• [Chronic kidney disease, new therapeutic approaches].

  La Revue du praticien 20120101

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

  Contributions to nephrology 20120101

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

  Drug design, development and therapy 20120101

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

  Journal of experimental therapeutics & oncology 20120101

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

  Anticancer research 20111101

• Bardoxolone: augmenting the Yin in chronic kidney disease.

  Diabetes & vascular disease research 20111001

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

  Toxicology and applied pharmacology 20110901

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

  Nature reviews. Nephrology 20110823

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

  The New England journal of medicine 20110728

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

  Free radical biology & medicine 20110701

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

  American journal of physiology. Renal physiology 20110501

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

  Journal of medicinal chemistry 20110324

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

  American journal of nephrology 20110101

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

  Journal of experimental therapeutics & oncology 20110101

• Bardoxolone methyl: a targeted antioxidant.

  Renal failure 20110101

• 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.

  The Journal of biological chemistry 20101224

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

  Cancer prevention research (Philadelphia, Pa.) 20101101

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

  The Journal of biological chemistry 20100903

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

  Spine 20100815

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

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

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

  Molecular cancer research : MCR 20100701

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

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

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

  Radiation research 20100701

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

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

• Fatty acid synthesis is a therapeutic target in human liposarcoma.

  International journal of oncology 20100501

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

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

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

  Anticancer research 20100301

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

  Biochemical pharmacology 20100201

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

  BMC cancer 20100101

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

  Molecular cancer 20100101

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

  Cancer prevention research (Philadelphia, Pa.) 20091201

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

  The Prostate 20090601

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

  Cancer chemotherapy and pharmacology 20090301

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

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

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

  Cancer research 20080915

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

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

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

  Leukemia 20080601

• 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.

  Molecular cancer therapeutics 20080501

• 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.

  Cancer research 20080415

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

  Journal of neuroinflammation 20080101

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

  Immunopharmacology and immunotoxicology 20080101

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

  Molecular cancer therapeutics 20071201

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

  Cancer biology & therapy 20071201

• 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.

  Antioxidants & redox signaling 20071101

• 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.

  Cancer biology & therapy 20071001

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

  Journal of neuro-oncology 20070901

• 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.

  Cancer research 20070501

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

  Cancer research 20070315

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

  Anticancer research 20070101

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

  The Journal of biological chemistry 20061124

• 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).

  Cancer biology & therapy 20060501

• 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.

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

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

  Leukemia 20050801

• 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.

  Cancer research 20041015

• 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 of medicinal chemistry 20040923

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

  Leukemia 20031101

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

  Bioorganic & medicinal chemistry letters 20020408

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

  Blood 20020101

• 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.

  Molecular cancer therapeutics 20020101

• 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.

  Molecular endocrinology (Baltimore, Md.) 20001001