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

Identification
NameBenzbromarone
Accession NumberDB12319
TypeSmall Molecule
GroupsInvestigational, Withdrawn
Description

Benzbromarone has been used in trials studying the basic science and treatment of Heart Failure, Hyperuricemia, Chronic Kidney Disease, Abnormal Renal Function, and Gout and Asymptomatic Hyperuricemia.

Structure
Thumb
Synonyms
2-ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran
3,5-dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone
External IDs L-2214 / MJ 10061
Product Ingredients Not Available
ProductsNot Available
International Brands
NameCompany
UroleapNot Available
Brand mixturesNot Available
Categories
UNII4POG0RL69O
CAS number3562-84-3
WeightAverage: 424.083
Monoisotopic: 421.915319544
Chemical FormulaC17H12Br2O3
InChI KeyWHQCHUCQKNIQEC-UHFFFAOYSA-N
InChI
InChI=1S/C17H12Br2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3
IUPAC Name
2,6-dibromo-4-(2-ethyl-1-benzofuran-3-carbonyl)phenol
SMILES
CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Cytochrome P450 2C9Proteinunknown
inhibitor
HumanP11712 details
Cytochrome P450 2C19Proteinunknown
inhibitor
HumanP33261 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesM04AB03 — Benzbromarone
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedBasic ScienceGout and Asymptomatic Hyperuricemia1
2CompletedTreatmentIdiopathic Pulmonary Arterial Hypertension1
2RecruitingTreatmentHyperuricemia1
3Active Not RecruitingTreatmentHyperuricemia With or Without Gout1
4CompletedTreatmentHeart Failure, Unspecified / Hyperuricemia1
Not AvailableNot Yet RecruitingTreatmentAbnormal Renal Function / Chronic Kidney Disease (CKD) / Hyperuricemia1
Not AvailableRecruitingTreatmentAbnormal Renal Function / Chronic Kidney Disease (CKD) / Hyperuricemia1
Properties
StateNot Available
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0131 mg/mLALOGPS
logP5.52ALOGPS
logP5.55ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)5.11ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.37 m3·mol-1ChemAxon
Polarizability35.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAryl-phenylketones
Alternative ParentsBenzofurans / O-bromophenols / Benzoyl derivatives / 3-aroylfurans / Bromobenzenes / Aryl bromides / Heteroaromatic compounds / Oxacyclic compounds / Organobromides / Organic oxides
SubstituentsAryl-phenylketone / Benzofuran / 3-aroylfuran / Benzoyl / 2-bromophenol / 2-halophenol / Phenol / Bromobenzene / Halobenzene / Aryl bromide
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors1-benzofurans, aromatic ketone (CHEBI:3023 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Uniprot Name:
Cytochrome P450 2C9
Molecular Weight:
55627.365 Da
References
  1. Locuson CW 2nd, Wahlstrom JL, Rock DA, Rock DA, Jones JP: A new class of CYP2C9 inhibitors: probing 2C9 specificity with high-affinity benzbromarone derivatives. Drug Metab Dispos. 2003 Jul;31(7):967-71. [PubMed:12814975 ]
  2. Locuson CW 2nd, Rock DA, Jones JP: Quantitative binding models for CYP2C9 based on benzbromarone analogues. Biochemistry. 2004 Jun 8;43(22):6948-58. [PubMed:15170332 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Uniprot Name:
Cytochrome P450 2C19
Molecular Weight:
55930.545 Da
References
  1. Locuson CW 2nd, Suzuki H, Rettie AE, Jones JP: Charge and substituent effects on affinity and metabolism of benzbromarone-based CYP2C19 inhibitors. J Med Chem. 2004 Dec 30;47(27):6768-76. [PubMed:15615526 ]
Drug created on October 20, 2016 15:56 / Updated on September 01, 2017 12:19