Bardoxolone methyl

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Bardoxolone methyl
Accession Number
DB05983
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-713200 / RTA 402 / RTA-402
Categories
UNII
CEG1Q6OGU1
CAS number
218600-53-4
Weight
Average: 505.699
Monoisotopic: 505.319208869
Chemical Formula
C32H43NO4
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

Pharmacology

Indication

Investigated for use/treatment in lymphoma (unspecified), multiple myeloma, and solid tumors.

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.

TargetActionsOrganism
UNF-kappa-B inhibitor alphaNot AvailableHumans
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
355161
BindingDB
217379
ChEMBL
CHEMBL1762621
Wikipedia
Bardoxolone_methyl

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers2
1CompletedTreatmentAdvanced Solid Tumors / Lymphoid Malignancies1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers / Hepatic Impairment1
1CompletedTreatmentLymphoid Malignancies / Tumors, Solid1
1TerminatedTreatmentChronic Kidney Disease (CKD) / Type 2 Diabetes Mellitus1
1TerminatedTreatmentRenal Insufficiency,Chronic / Type 2 Diabetes Mellitus1
1WithdrawnTreatmentRenal Insufficiency,Chronic / Type 2 Diabetes Mellitus1
1, 2TerminatedTreatmentLiver Diseases1
1, 2TerminatedTreatmentMalignant Neoplasm of Pancreas / Neoplasms, Pancreatic1
2Active Not RecruitingTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD) / CKD Associated With Type 1 Diabetes / Glomerulosclerosis, Focal Segmental / IgA Nephropathy1
2CompletedTreatmentAcute interstitial pneumonitis / Cryptogenic Organizing Pneumonia / Desquamative Interstitial Pneumonia / Idiopathic Interstitial Pneumonias / Idiopathic Lymphoid Interstitial Pneumonia / Idiopathic Pleuroparenchymal Fibroelastosis / Idiopathic Pulmonary Fibrosis (IPF) / Interstitial Lung Disease (ILD) / Pulmonary Arterial Hypertension (PAH) / Pulmonary Hypertension (PH) / Respiratory Bronchiolitis Associated Interstitial Lung Disease / Sarcoidosis1
2CompletedTreatmentChronic Kidney Disease (CKD) / Diabetic Nephropathies / Type 2 Diabetes Mellitus1
2CompletedTreatmentChronic Kidney Disease (CKD) / Type 2 Diabetes Mellitus1
2CompletedTreatmentDiabetic Nephropathies1
2CompletedTreatmentRenal Insufficiency,Chronic / Type 2 Diabetes Mellitus1
2TerminatedTreatmentChronic Kidney Disease (CKD) / Type 2 Diabetes Mellitus2
2WithdrawnTreatmentEnd-Stage Renal Disease (ESRD) / Type 2 Diabetes Mellitus1
2WithdrawnTreatmentRenal Insufficiency,Chronic / Type 2 Diabetes Mellitus1
2, 3Active Not RecruitingTreatmentAlport Syndrome1
3RecruitingTreatmentAlport Syndrome / Autosomal Dominant Polycystic Kidney Disease (ADPKD) / Chronic Kidney Disease (CKD) / CKD Associated With Type 1 Diabetes / Glomerulosclerosis, Focal Segmental / IgA Nephropathy1
3RecruitingTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD)1
3RecruitingTreatmentConnective Tissue Disease-Associated Pulmonary Arterial Hypertension1
3RecruitingTreatmentDiabetic Kidney Disease1
3RecruitingTreatmentPulmonary Hypertension (PH)1
3TerminatedTreatmentRenal Insufficiency,Chronic / Type 2 Diabetes Mellitus1

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
PropertyValueSource
Water Solubility0.00294 mg/mLALOGPS
logP5.29ALOGPS
logP6.55ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area84.23 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity144.36 m3·mol-1ChemAxon
Polarizability58.23 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Classification
Not classified

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 on November 18, 2007 11:29 / Updated on June 04, 2019 06:20