Bardoxolone methyl
Identification
- Generic Name
- Bardoxolone methyl
- DrugBank Accession Number
- DB05983
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 505.699
Monoisotopic: 505.319208869 - Chemical Formula
- C32H43NO4
- Synonyms
- Bardoxolone methyl
- External IDs
- NSC-713200
- RTA 402
- RTA-402
Pharmacology
- Indication
Investigated for use/treatment in lymphoma (unspecified), multiple myeloma, and solid tumors.
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- Pharmacodynamics
Not Available
- Mechanism of action
RTA 402 inhibits the activity of nuclear factor kappa-B (NF-kB) activated by tumor necrosis factor (TNF) and other inflammatory agents in a variety of cancer cells. It is a novel targeted cancer therapy with a unique mechanism of action. It exploits fundamental physiological differences between cancerous and noncancerous cells by modulating oxidative stress response pathways. As a result, the drug is toxic to cancer cells but induces protective antioxidant and anti-inflammatory responses in normal cells.
Target Actions Organism UNF-kappa-B inhibitor alpha Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Cyclohexenones
- Alternative Parents
- Methyl esters / Nitriles / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic homopolycyclic compound / Carbonitrile / Carboxylic acid derivative / Carboxylic acid ester / Cyclohexenone / Hydrocarbon derivative / Methyl ester / Monocarboxylic acid or derivatives / Nitrile / Organic nitrogen compound
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- CEG1Q6OGU1
- CAS number
- 218600-53-4
- InChI Key
- WPTTVJLTNAWYAO-KPOXMGGZSA-N
- InChI
- InChI=1S/C32H43NO4/c1-27(2)11-13-32(26(36)37-8)14-12-31(7)24(20(32)17-27)21(34)15-23-29(5)16-19(18-33)25(35)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,29-,30+,31+,32-/m0/s1
- IUPAC Name
- methyl (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-carboxylate
- SMILES
- COC(=O)[C@]12CCC(C)(C)C[C@H]1[C@H]1C(=O)C=C3[C@@]4(C)C=C(C#N)C(=O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2
References
- General References
- Not Available
- External Links
- ChemSpider
- 355161
- BindingDB
- 217379
- ChEMBL
- CHEMBL1762621
- ZINC
- ZINC000003982151
- Wikipedia
- Bardoxolone_methyl
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Alport Syndrome / Autosomal Dominant Polycystic Kidney Disease (ADPKD) / Chronic Kidney Disease (CKD) 1 3 Terminated Treatment Autosomal Dominant Polycystic Kidney Disease (ADPKD) 1 3 Terminated Treatment Connective Tissue Disease-Associated Pulmonary Arterial Hypertension 1 3 Terminated Treatment Diabetic Kidney Disease (DKD) 1 3 Terminated Treatment Pulmonary Hypertension (PH) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00294 mg/mL ALOGPS logP 5.29 ALOGPS logP 6.55 Chemaxon logS -5.2 ALOGPS pKa (Strongest Basic) -5.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 84.23 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 144.36 m3·mol-1 Chemaxon Polarizability 58.23 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 227.3474571 predictedDarkChem Lite v0.1.0 [M-H]- 230.59073 predictedDeepCCS 1.0 (2019) [M+H]+ 227.8101571 predictedDarkChem Lite v0.1.0 [M+H]+ 232.24393 predictedDeepCCS 1.0 (2019) [M+Na]+ 227.8247571 predictedDarkChem Lite v0.1.0 [M+Na]+ 238.40077 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Inhibits the activity of dimeric NF-kappa-B/REL complexes by trapping REL dimers in the cytoplasm through masking of their nuclear localization signals. On cellular stimulation by immune and proinf...
- Gene Name
- NFKBIA
- Uniprot ID
- P25963
- Uniprot Name
- NF-kappa-B inhibitor alpha
- Molecular Weight
- 35608.65 Da
Drug created at November 18, 2007 18:29 / Updated at April 12, 2023 21:54