Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0193)
Drug Name
Benzbromarone
Synonyms
Benzbromaron; Benzbromarone [USAN:INN:BAN]; Benzbromaronum [INN-Latin]; Benzobromarona [INN-Spanish]; Besuric; Desuric; Exurate; Harolan; Azubromaron; Hipurik; L 2214; L 2214-Labaz; L-2214; L2214-Labaz; MJ 10061; Minuric; Narcaricin; Normurat; Uricovac; Urinorm; Uroleap (TN); benzbromarone; 2-Ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran; 3,5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone; 3562-84-3; Methanone, (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-3-benzofuranyl)-; NSC 85433
Indication Hyperuricaemia [ICD11: 5C55] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 424.1 Topological Polar Surface Area 50.4
Heavy Atom Count 22 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2333
PubChem SID
122758 ; 221763 ; 855676 ; 4253342 ; 4572619 ; 7848119 ; 8139271 ; 8151561 ; 10320943 ; 10321664 ; 11110651 ; 11446236 ; 11458917 ; 11461081 ; 11466398 ; 11467518 ; 11486156 ; 11533498 ; 15329540 ; 24424558 ; 24891861 ; 26653345 ; 26664708 ; 29221503 ; 46386951 ; 47291274 ; 47810917 ; 47959937 ; 48185143 ; 48259414 ; 48415612 ; 49681786 ; 49698460 ; 49988150 ; 50100155 ; 50103990 ; 50804618 ; 56422114 ; 57321259 ; 57653945 ; 76715662 ; 85787503 ; 89471954 ; 92125465 ; 92308014 ; 92308634 ; 92722452 ; 99450936 ; 103513016 ; 103914152
ChEBI ID
ChEBI:3023
CAS Number
3562-84-3
TTD Drug ID
D0Z3DY
Formula
C17H12Br2O3
Canonical SMILES
CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Benzbromarone metabolite M5 DM001641 N. A. Oxidation - Hydroxylation 1 [4]
Benzbromarone metabolite M6 DM001639 N. A. Oxidation - Hydroxylation 1 [4]
Benzbromarone metabolite M6 DM001639 N. A. Unclear 1 [4]
Benzbromarone metabolite M7 DM001635 N. A. Unclear 1 [4]
Benzbromarone metabolite M14 DM001643 N. A. Unclear 2 [4]
Benzbromarone metabolite M15 DM001642 N. A. Unclear 2 [4]
Benzbromarone metabolite M4 DM001636 N. A. Unclear 2 [4]
Benzbromarone metabolite M2 DM001637 N. A. Unclear 3 [4]
Benzbromarone metabolite M3 DM001640 N. A. Unclear 3 [4]
Benzbromarone metabolite M1 DM001638 N. A. Unclear 4 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003476 Benzbromarone Benzbromarone metabolite M7 Unclear CYP3A4 ... [4]
MR003477 Benzbromarone Benzbromarone metabolite M6 Unclear Unclear [4]
MR003478 Benzbromarone Benzbromarone metabolite M5 Oxidation - Hydroxylation Unclear [4]
MR003475 Benzbromarone metabolite M5 Benzbromarone metabolite M15 Unclear Unclear [4]
MR003472 Benzbromarone metabolite M6 Benzbromarone metabolite M4 Unclear Unclear [4]
MR003473 Benzbromarone metabolite M6 Benzbromarone metabolite M15 Unclear Unclear [4]
MR003474 Benzbromarone metabolite M6 Benzbromarone metabolite M14 Unclear Unclear [4]
MR003468 Benzbromarone metabolite M7 Benzbromarone metabolite M4 Unclear Unclear [4]
MR003469 Benzbromarone metabolite M4 Benzbromarone metabolite M2 Unclear Unclear [4]
MR003470 Benzbromarone metabolite M4 Benzbromarone metabolite M3 Unclear Unclear [4]
MR003471 Benzbromarone metabolite M2 Benzbromarone metabolite M1 Unclear Unclear [4]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [3]
References
1 ClinicalTrials.gov (NCT00422318) Treatment of Hyperuricemia in Patients With Heart Failure.
2 Quantitative binding models for CYP2C9 based on benzbromarone analogues. Biochemistry. 2004 Jun 8;43(22):6948-58.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Identification of Epoxide-Derived Metabolite(s) of Benzbromarone

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