Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-13 11:41:48 UTC |
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Update Date | 2022-03-07 02:57:12 UTC |
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HMDB ID | HMDB0041834 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Benzbromarone |
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Description | Benzbromarone (INN) is a uricosuric agent used in the treatment of gout, especially when allopurinol, a first-line treatment, fails or produces intolerable adverse effects. It is structurally related to the antiarrhythmic amiodarone. Benzbromarone is a very potent inhibitor of CYP2C9. Several analogues of the drug have been developed as CYP2C9 and CYP2C19 inhibitors for use in research. |
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Structure | CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1 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 |
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Synonyms | Value | Source |
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2-Ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran | ChEBI | 3,5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone | ChEBI | Uroleap | ChEBI | (3,5-Dibromo-4-hydroxyphenyl)(2-ethyl-1-benzofuran-3-yl)methanone | HMDB | 3, 5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone | HMDB | Benzbromaron | HMDB | Benzbromarone(usan) | HMDB | Desuric | HMDB | Exurate | HMDB | Hipurik | HMDB | Ketone, 3,5-dibromo-4-hydroxyphenyl 2-ethyl-3-benzofuranyl | HMDB | L 2214-Labaz | HMDB | Minuric | HMDB | Normurat | HMDB | Uricovac | HMDB | Urinorm | HMDB | AL, benzbromaron | HMDB | Aliud brand OF benzbromarone | HMDB | Benzbromaron al | HMDB | Besuric | HMDB | Sanfer brand OF benzbromarone | HMDB | Ratiopharm brand OF benzbromarone | HMDB | Acifugan | HMDB | Benzbromaronratiopharm | HMDB | Heumann brand OF benzbromarone | HMDB | Benzbromaron ratiopharm | HMDB | Benzbromarone aliud brand | HMDB | Benzbromarone heumann brand | HMDB | Benzbromarone sanfer brand | HMDB | Benzbromarone ratiopharm brand | HMDB | Narcaricin | HMDB | Sanofi winthrop brand OF benzbromarone | HMDB | Benzbromaron-ratiopharm | HMDB |
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Chemical Formula | C17H12Br2O3 |
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Average Molecular Weight | 424.083 |
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Monoisotopic Molecular Weight | 421.915319544 |
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IUPAC Name | 2,6-dibromo-4-(2-ethyl-1-benzofuran-3-carbonyl)phenol |
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Traditional Name | benzbromarone |
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CAS Registry Number | 3562-84-3 |
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SMILES | CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1 |
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InChI Identifier | 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 |
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InChI Key | WHQCHUCQKNIQEC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Aryl-phenylketones |
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Alternative Parents | |
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Substituents | - Aryl-phenylketone
- Benzofuran
- 3-aroylfuran
- Benzoyl
- 2-bromophenol
- 2-halophenol
- Phenol
- Bromobenzene
- Halobenzene
- Aryl bromide
- Aryl halide
- Monocyclic benzene moiety
- Benzenoid
- Heteroaromatic compound
- Furan
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Hydrocarbon derivative
- Organobromide
- Organohalogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 151 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Benzbromarone GC-MS (Non-derivatized) - 70eV, Positive | splash10-05i1-4832900000-7ab986576555401c2682 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzbromarone GC-MS (1 TMS) - 70eV, Positive | splash10-00e9-9503700000-00cd0af3f4c2c3b65960 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzbromarone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzbromarone 35V, Negative-QTOF | splash10-00di-0000900000-94d07af34f38fb48d939 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Positive-QTOF | splash10-00di-0120900000-fc249a1eb88559bbcbb1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Positive-QTOF | splash10-00b9-0591400000-e59e173f15483ef2be8f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Positive-QTOF | splash10-004j-1290000000-c6ab434e069c23434652 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Negative-QTOF | splash10-00di-0000900000-65ce336d84ac3bc1b6cf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Negative-QTOF | splash10-00di-0332900000-1e5e89c78006263a0948 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Negative-QTOF | splash10-0005-2931000000-017d942ea5bfdf5d7a10 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Negative-QTOF | splash10-00di-0000900000-dacd5da7c3b80a31dd02 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Negative-QTOF | splash10-00di-4000900000-8beeba5ecf13d3cdd46c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Negative-QTOF | splash10-004i-9000000000-abb69a363cc923ebb9e1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Positive-QTOF | splash10-00di-0000900000-2199f895a98ec54296c3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Positive-QTOF | splash10-00fr-0180900000-6045f757598f9ed9a40f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Positive-QTOF | splash10-004l-1590000000-09a3248599d038d0c11b | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB12319 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2243 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Benzbromarone |
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METLIN ID | Not Available |
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PubChem Compound | 2333 |
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PDB ID | Not Available |
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ChEBI ID | 3023 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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