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- Investigational, Withdrawn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
Structure for Benzbromarone (DB12319)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Gouty arthritis •••••••••••• ••••••• •••••• Used in combination to treat Gouty arthritis Combination Product in combination with: Allopurinol (DB00437) •••••••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCytochrome P450 2C9 inhibitorHumans UCytochrome P450 2C19 inhibitorHumans - 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbrocitinib The metabolism of Abrocitinib can be decreased when combined with Benzbromarone. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Benzbromarone. Acetohexamide The metabolism of Acetohexamide can be decreased when combined with Benzbromarone. Acetylsalicylic acid The therapeutic efficacy of Benzbromarone can be decreased when used in combination with Acetylsalicylic acid. Albendazole The metabolism of Albendazole can be decreased when combined with Benzbromarone. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Uroleap
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ลาโนโลน Benzbromarone (20 mg) + Allopurinol (100 mg) Tablet, coated Oral บริษัท เภสัชกรรมศรีประสิทธิ์ จำกัด จำกัด 1997-12-10 Not applicable Thailand 
Categories
- ATC Codes
- M04AB03 — Benzbromarone
- Drug Categories
- Antigout Preparations
- Antirheumatic Agents
- Benzofurans
- BSEP/ABCB11 Substrates
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Musculo-Skeletal System
- OATP1B1/SLCO1B1 Inhibitors
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Preparations Increasing Uric Acid Excretion
- Uricosuric Agents
- 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
- External Links
- Human Metabolome Database
- HMDB0041834
- KEGG Drug
- D01056
- PubChem Compound
- 2333
- PubChem Substance
- 347828582
- ChemSpider
- 2243
- BindingDB
- 50158460
- 1385
- ChEBI
- 3023
- ChEMBL
- CHEMBL388590
- ZINC
- ZINC000000608205
- PDBe Ligand
- R75
- Wikipedia
- Benzbromarone
- PDB Entries
- 7acu / 7d6j / 8ii2 / 8k4h
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Heart Failure / Hyperuricemia 1 4 Completed Treatment Type 2 Diabetes Mellitus 1 4 Unknown Status Treatment Hyperuricemia / Left Ventricular Diastolic Dysfunction / Syndrome, Metabolic 1 3 Completed Treatment Hyperuricemia With or Without Gout 1 2 Completed Treatment Hyperuricemia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet Oral 50 mg Tablet, coated Oral Tablet, coated Oral 100 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0131 mg/mL ALOGPS logP 5.52 ALOGPS logP 5.55 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 5.11 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 50.44 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 92.37 m3·mol-1 Chemaxon Polarizability 35.65 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-05i1-4832900000-7ab986576555401c2682 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1000900000-fd609f1f074581b3f97a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0000900000-ca18770a6965b267fa70 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0000900000-2166dea0b6a53beee9b8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00fu-4256900000-de9a61a12c52f64a466b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-002b-0981100000-610847848e25dfc99d6b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9003000000-3bcd1e0ca220ac5f90c6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.1333929 predictedDarkChem Lite v0.1.0 [M-H]- 168.25583 predictedDeepCCS 1.0 (2019) [M+H]+ 176.0641929 predictedDarkChem Lite v0.1.0 [M+H]+ 170.61382 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.1058929 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.25386 predictedDeepCCS 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
- 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]
- 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
- 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
- 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]
- 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
- 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
- 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
- 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