Benzbromarone

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

Identification

Summary

Benzbromarone is a uricosuric agent which is taken daily for the prevention of gout flares.

Generic Name
Benzbromarone
DrugBank Accession Number
DB12319
Background

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.

Type
Small Molecule
Groups
Investigational, Withdrawn
Structure
Weight
Average: 424.083
Monoisotopic: 421.915319544
Chemical Formula
C17H12Br2O3
Synonyms
  • 2-ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran
  • 3,5-dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone
  • Benzbromarona
  • Benzbromarone
External IDs
  • L-2214
  • MJ 10061

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGouty arthritis••••••••••••••••••• ••••••
Used in combination to treatGouty arthritisCombination Product in combination with: Allopurinol (DB00437)••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCytochrome P450 2C9
inhibitor
Humans
UCytochrome P450 2C19
inhibitor
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
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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.
DrugInteraction
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Benzbromarone.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Benzbromarone.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Benzbromarone.
Acetylsalicylic acidThe therapeutic efficacy of Benzbromarone can be decreased when used in combination with Acetylsalicylic acid.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Benzbromarone.
Food Interactions
Not Available

Products

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International/Other Brands
Uroleap
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ลาโนโลนBenzbromarone (20 mg) + Allopurinol (100 mg)Tablet, coatedOralบริษัท เภสัชกรรมศรีประสิทธิ์ จำกัด จำกัด1997-12-10Not applicableThailand flag

Categories

ATC Codes
M04AB03 — Benzbromarone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl-phenylketones
Alternative Parents
Benzofurans / O-bromophenols / Benzoyl derivatives / 3-aroylfurans / Bromobenzenes / Aryl bromides / Heteroaromatic compounds / Oxacyclic compounds / Organobromides / Organic oxides
show 1 more
Substituents
2-bromophenol / 2-halophenol / 3-aroylfuran / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Aryl-phenylketone / Benzenoid / Benzofuran / Benzoyl
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
1-benzofurans, aromatic ketone (CHEBI:3023)
Affected organisms
Not Available

Chemical Identifiers

UNII
4POG0RL69O
CAS number
3562-84-3
InChI Key
WHQCHUCQKNIQEC-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

References

General References
  1. FDA Thailand Product Information: Benarone (benzbromarone) oral tablets [Link]
  2. FDA Thailand Product Information: Allomaron (allopurinol/benzbromarone) oral tablets [Link]
Human Metabolome Database
HMDB0041834
KEGG Drug
D01056
PubChem Compound
2333
PubChem Substance
347828582
ChemSpider
2243
BindingDB
50158460
RxNav
1385
ChEBI
3023
ChEMBL
CHEMBL388590
ZINC
ZINC000000608205
PDBe Ligand
R75
Wikipedia
Benzbromarone
PDB Entries
7acu / 7d6j / 8ii2 / 8k4h

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHeart Failure / Hyperuricemia1
4CompletedTreatmentType 2 Diabetes Mellitus1
4Unknown StatusTreatmentHyperuricemia / Left Ventricular Diastolic Dysfunction / Syndrome, Metabolic1
3CompletedTreatmentHyperuricemia With or Without Gout1
2CompletedTreatmentHyperuricemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
TabletOral50 mg
Tablet, coatedOral
Tablet, coatedOral100 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0131 mg/mLALOGPS
logP5.52ALOGPS
logP5.55Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)5.11Chemaxon
pKa (Strongest Basic)-3Chemaxon
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 Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05i1-4832900000-7ab986576555401c2682
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1000900000-fd609f1f074581b3f97a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-ca18770a6965b267fa70
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-2166dea0b6a53beee9b8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fu-4256900000-de9a61a12c52f64a466b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-0981100000-610847848e25dfc99d6b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9003000000-3bcd1e0ca220ac5f90c6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-176.1333929
predicted
DarkChem Lite v0.1.0
[M-H]-168.25583
predicted
DeepCCS 1.0 (2019)
[M+H]+176.0641929
predicted
DarkChem Lite v0.1.0
[M+H]+170.61382
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.1058929
predicted
DarkChem Lite v0.1.0
[M+Na]+177.25386
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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 un...
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Anionic analog is a more potent 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 im...
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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data supporting this enzyme inhibition is limited. Current evidence shows that it may be synthetically modified to become a very potent CYP2C19 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 im...
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. [Article]
  2. Reynald RL, Sansen S, Stout CD, Johnson EF: Structural characterization of human cytochrome P450 2C19: active site differences between P450s 2C8, 2C9, and 2C19. J Biol Chem. 2012 Dec 28;287(53):44581-91. doi: 10.1074/jbc.M112.424895. Epub 2012 Nov 1. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created at October 20, 2016 21:56 / Updated at May 27, 2021 02:57