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
Topological Polar Surface Area (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]
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 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
8 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
9 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
10 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
11 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
12 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
13 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
14 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
15 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
16 Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7.
17 Nat Rev Drug Discov. 2013 Feb;12(2):87-90.
18 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 708).
19 Species-dependent transport and modulation properties of human and mouse multidrug resistance protein 2 (MRP2/Mrp2, ABCC2/Abcc2). Drug Metab Dispos. 2008 Apr;36(4):631-40.
20 Functional assay and structure-activity relationships of new third-generation P-glycoprotein inhibitors. Bioorg Med Chem. 2008 Mar 1;16(5):2448-62.
21 Topological model for the prediction of MRP1 inhibitory activity of pyrrolopyrimidines and templates derived from pyrrolopyrimidine. Bioorg Med Chem Lett. 2005 Nov 15;15(22):4967-72.