Details of the Drug

General Information of Drug (ID: DMC3YUA)

Drug Name
Benzbromarone
Synonyms
Acifugan; Azubromaron; Benzbromaron; Benzbromaronratiopharm; Benzbromaronum; Benzobromarona; Besuric; Desuric; Exurate; Harolan; Hipurik; Minuric; Narcaricin; Normurat; Uricovac; Urinorm; Uroleap; Aliud Brand of Benzbromarone; Benzbromaron AL; Benzbromaron ratiopharm; Benzbromarone Aliud Brand; Benzbromarone Heumann Brand; Benzbromarone Sanfer Brand; Benzbromarone ratiopharm Brand; Heumann Brand of Benzbromarone; Ratiopharm Brand of Benzbromarone; Sanfer Brand of Benzbromarone; Sanofi Winthrop Brand of Benzbromarone; L 2214; L2214; MJ 10061; NCI85433; AL, Benzbromaron; Benzbromaron-ratiopharm; Benzbromaronum [INN-Latin]; Benzobromarona [INN-Spanish]; L 2214-Labaz; L-2214; Uroleap (TN); Benzbromarone [USAN:INN:BAN]; Methanone, (3; Benzbromarone (JP15/USAN/INN); KETONE, 3,5-DIBROMO-4-HYDROXYPHENYL 2-ETHYL-3-BENZOFURANYL; Ketone, 3,5-dibromo-4-hydroxyphenyl 2-ethyl-3-benzofuranyl; (2-Ethyl-3-benzofuranyl)-(3,5-dibrom-4-hydroxyphenyl)keton; (3,5-Dibromo-4-hydroxyphenyl)(2-ethyl-1-benzofuran-3-yl)methanone; (3,5-dibromo-4-hydroxyphenyl)-(2-ethyl-1-benzofuran-3-yl)methanone; 2-Ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran; 3, 5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone; 3,5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone; 3-(3,5-Dibromo-4-hydroxybenzoyl)-2-ethylbenzofuran; 3-[3,5-DIBROMO-4-HYDROXYBENZOYL]-2-ETHYLBENZOFURAN
Indication
Disease Entry ICD 11 Status REF
Gout FA25 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 424.1
Logarithm of the Partition Coefficient (xlogp) 5.7
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Chemical Identifiers
Formula
C17H12Br2O3
IUPAC Name
(3,5-dibromo-4-hydroxyphenyl)-(2-ethyl-1-benzofuran-3-yl)methanone
Canonical SMILES
CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br
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
InChIKey
WHQCHUCQKNIQEC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2333
ChEBI ID
CHEBI:3023
CAS Number
3562-84-3
DrugBank ID
DB12319
TTD ID
D0Z3DY
VARIDT ID
DR00327
INTEDE ID
DR0193

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Calcium-dependent chloride channel anoctamin (ANO) TTOJI4S ANO1_HUMAN Antagonist [3]
Multidrug resistance-associated protein 1 (ABCC1) TTOI92F MRP1_HUMAN Stimulator [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 6 (ABCC6) DT582KR MRP6_HUMAN Substrate [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Adiponectin (ADIPOQ) OTNX23LE ADIPO_HUMAN Gene/Protein Processing [7]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [8]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [8]
Aldo-keto reductase family 1 member C4 (AKR1C4) OTW2MMOF AK1C4_HUMAN Gene/Protein Processing [8]
Angiotensin-converting enzyme 2 (ACE2) OTTRZGU7 ACE2_HUMAN Gene/Protein Processing [9]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [10]
ATP-binding cassette sub-family C member 6 (ABCC6) OTZT0LKT MRP6_HUMAN Gene/Protein Processing [11]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [12]
C-reactive protein (CRP) OT0RFT8F CRP_HUMAN Gene/Protein Processing [13]
Carnitine O-palmitoyltransferase 1, liver isoform (CPT1A) OTI862QH CPT1A_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Gout
ICD Disease Classification FA25
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Multidrug resistance-associated protein 1 (ABCC1) DTT ABCC1 1.01E-02 0.89 1.34
Multidrug resistance-associated protein 6 (ABCC6) DTP MRP6 4.46E-02 8.66E-02 5.02E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.69E-01 6.97E-02 1.48E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Anoctamin Channels in Human Myometrium: A Novel Target for Tocolysis.Reprod Sci. 2018 Nov;25(11):1589-1600.
4 Transport of diclofenac by breast cancer resistance protein (ABCG2) and stimulation of multidrug resistance protein 2 (ABCC2)-mediated drug transpo... Drug Metab Dispos. 2009 Jan;37(1):129-36.
5 The Transporter Classification Database (TCDB): recent advances. Nucleic Acids Res. 2016 Jan 4;44(D1):D372-9. (ID: 3.A.1.208.10)
6 Quantitative binding models for CYP2C9 based on benzbromarone analogues. Biochemistry. 2004 Jun 8;43(22):6948-58.
7 Effects of benzbromarone and allopurinol on adiponectin in vivo and in vitro. Horm Metab Res. 2009 Apr;41(4):327-32. doi: 10.1055/s-0028-1102947. Epub 2008 Dec 1.
8 Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. Chem Biol Interact. 2003 Feb 1;143-144:503-13.
9 Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
10 In vitro approach to assess the potential for risk of idiosyncratic adverse reactions caused by candidate drugs. Chem Res Toxicol. 2012 Aug 20;25(8):1616-32. doi: 10.1021/tx300091x. Epub 2012 May 31.
11 Multidrug resistance protein-6 (MRP6) in human dermal fibroblasts. Comparison between cells from normal subjects and from Pseudoxanthoma elasticum patients. Matrix Biol. 2003 Nov;22(6):491-500. doi: 10.1016/j.matbio.2003.09.001.
12 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
13 Serum CRP in patients with gout and effects of benzbromarone. Int J Clin Pharmacol Ther. 2011 Mar;49(3):191-7. doi: 10.5414/cp201425.
14 Hepatocellular toxicity of benzbromarone: effects on mitochondrial function and structure. Toxicology. 2014 Oct 3;324:136-46. doi: 10.1016/j.tox.2014.08.002. Epub 2014 Aug 7.