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

General Information of Drug (ID: DR0926)
Drug Name
Lesinurad
Synonyms
Lesinured [USAN]; AK323774; C17H14BrN3O2S; UNII-09ERP08I3W; LESINURAD; RDEA 594; RDEA-594; RDEA594; Zurampic; 09ERP08I3W; 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid; 2-(5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid; 2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid; 2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetic acid; 878672-00-5
Indication Uncontrolled gout [ICD11: FA25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 404.3 Topological Polar Surface Area 93.3
Heavy Atom Count 24 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
53465279
PubChem SID
135267370 ; 135626658 ; 141682643 ; 160698094 ; 163620844 ; 163686172 ; 186022493 ; 198964591 ; 223366008 ; 224297829 ; 227115271 ; 243322229 ; 251963128 ; 252216185 ; 252440600 ; 252479355
ChEBI ID
CHEBI:90929
CAS Number
878672-00-5
TTD Drug ID
D0C3SW
Formula
C17H14BrN3O2S
Canonical SMILES
C1CC1C2=CC=C(C3=CC=CC=C23)N4C(=NN=C4Br)SCC(=O)O
InChI
1S/C17H14BrN3O2S/c18-16-19-20-17(24-9-15(22)23)21(16)14-8-7-11(10-5-6-10)12-3-1-2-4-13(12)14/h1-4,7-8,10H,5-6,9H2,(H,22,23)
InChIKey
FGQFOYHRJSUHMR-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
Lesinurad metabolite M3 DM000240
130381856
Oxidation - Hydroxylation 1 [2]
Lesinurad metabolite M3a DM000242 N. A. Oxidation - Hydroxylation 1 [2]
Lesinurad metabolite M3b DM000243 N. A. Oxidation - Hydroxylation 1 [2]
Lesinurad metabolite M3c DM000238 N. A. Oxidation - Oxidation 1 [2]
Lesinurad metabolite M6 DM000241
53402949
Unclear 1 [2]
Lesinurad metabolite M4 DM000239
130381854
Oxidation - N-Dealkylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003107 Lesinurad Lesinurad metabolite M3c Oxidation - Oxidation CYP2C9 [2]
MR003108 Lesinurad Lesinurad metabolite M3 Oxidation - Hydroxylation CYP2C9 ... [2]
MR003109 Lesinurad Lesinurad metabolite M6 Unclear CYP3A4 ... [2]
MR003110 Lesinurad Lesinurad metabolite M3a Oxidation - Hydroxylation CYP2C9 [2]
MR003111 Lesinurad Lesinurad metabolite M3b Oxidation - Hydroxylation CYP2C9 [2]
MR003106 Lesinurad metabolite M3c Lesinurad metabolite M4 Oxidation - N-Dealkylation Unclear [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Lesinurad was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of Stereoselective Metabolism, Inhibitory Effect on Uric Acid Uptake Transporters, and Pharmacokinetics of Lesinurad Atropisomers Drug Metab Dispos. 2019 Feb;47(2):104-113. doi: 10.1124/dmd.118.080549.

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