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

General Information of Drug (ID: DR1620)
Drug Name
Torasemide
Synonyms
Torasemida; Torasemida [INN-Spanish]; Torasemide; Torasemide, Anhydrous; Torasemidum; Torasemidum [INN-Latin]; Torsemide (Demadex); Demadex; JDL 464; JDL-464; Luprac; TORSEMIDE; W31X2H97FB; 1-Isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)urea; 56211-40-6; AC 4464; AC-4464; AC4464; BM 02015; BM-02015; BRN 0498515; CCRIS 6736; CHEBI:9637; MLS001165687; N-(((1-Methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulfonamide; N-(Isopropylcarbamoyl)-4-(m-tolylamino)pyridine-3-sulfonamide; Torem; UNII-W31X2H97FB
Indication Congestive heart failure [ICD11: BD10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 348.4 Topological Polar Surface Area 109
Heavy Atom Count 24 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
41781
PubChem SID
7585786 ; 7847448 ; 8177279 ; 11112793 ; 11364670 ; 11367232 ; 11369794 ; 11373102 ; 11373959 ; 11377957 ; 11467058 ; 11468178 ; 11484799 ; 11486816 ; 11488958 ; 11491647 ; 11492105 ; 11495590 ; 11528723 ; 12012656 ; 14900728 ; 25819958 ; 26612831 ; 26680347 ; 26719820 ; 26748988 ; 26748989 ; 34707389 ; 46386585 ; 46504760 ; 47291390 ; 47515595 ; 47515596 ; 47736767 ; 48259511 ; 48334790 ; 48416649 ; 49665992 ; 49666477 ; 49681707 ; 49699258 ; 49833537 ; 50107501 ; 53789088 ; 56313713 ; 57312605 ; 80124867 ; 81040892 ; 85788916 ; 87560438
ChEBI ID
CHEBI:9637
CAS Number
56211-40-6
TTD Drug ID
D0J9XZ
Formula
C16H20N4O3S
Canonical SMILES
CC1=CC(=CC=C1)NC2=C(C=NC=C2)S(=O)(=O)NC(=O)NC(C)C
InChI
1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)
InChIKey
NGBFQHCMQULJNZ-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
Torasemide metabolite M1 (hydroxytorsemide) DM006330
14475217
Oxidation - Hydrolyzationn 1 [4]
Torasemide metabolite M2 DM006333
86141019
Reduction - Reduction 1 [4]
Torasemide metabolite M3 DM006334
23656876
Oxidation - Hydrolyzationn 1 [4]
Torasemide metabolite M4 DM006332 N. A. Oxidation - Hydrolyzationn 1 [4]
Torasemide metabolite M5 DM006331
14475218
Oxidation - Carboxylation 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006800 Torasemide Torasemide metabolite M1 (hydroxytorsemide) Oxidation - Hydrolyzationn CYP2C8 ... [4]
MR006802 Torasemide Torasemide metabolite M4 Oxidation - Hydrolyzationn CYP2C8 ... [4]
MR006803 Torasemide Torasemide metabolite M2 Reduction - Reduction CYP2C8 ... [4]
MR006804 Torasemide Torasemide metabolite M3 Oxidation - Hydrolyzationn CYP2C8 ... [4]
MR006801 Torasemide metabolite M1 (hydroxytorsemide) Torasemide metabolite M5 Oxidation - Carboxylation Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
References
1 Torasemide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. J Pharmacol Exp Ther. 2004 Dec;311(3):996-1007.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
4 Simultaneous determination of torasemide and its major metabolite M5 in human urine by high-performance liquid chromatography-electrochemical detection
5 Pharmacokinetics and metabolism of torasemide in man

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