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

General Information of Drug (ID: DR0757)
Drug Name
Furosemide
Synonyms
Frusemid; Frusemide; Frusemin; Frusenex; Frusetic; Frusid; Fulsix; Fuluvamide; Furanthril; Furanthryl; Furantril; Furanturil; Furesis; Furosedon; Furosemid; Fursemid; Fursemide; Hydro-rapid; Impugan; Katlex; Lasilix; Lowpstron; Aisemide; Aluzine; Apo-Frusemide; Beronald; Desdemin; Diural; Dryptal; Errolon; Eutensin; Macasirool; Prefemin; Profemin; Promedes; Radonna; Rosemide; Rusyde; Seguril; Selectofur; Spirofur; Synephron; Transit; Trofurit; Uremide; Uresix; Urosemide; Yidoli; furosemide; 54-31-9; Disal; Fusid; Lasex; Lasix; Laxur; Lazix; Salix; Urex; Urian
Indication Congestive heart failure [ICD11: BD10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 330.74 Topological Polar Surface Area 131
Heavy Atom Count 21 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
3440
PubChem SID
9229 ; 140841 ; 597353 ; 5651429 ; 7847397 ; 8149353 ; 8152188 ; 10321703 ; 11112125 ; 11335750 ; 11360989 ; 11363994 ; 11366556 ; 11369118 ; 11371374 ; 11374398 ; 11377280 ; 11461961 ; 11466369 ; 11467489 ; 11484865 ; 11486058 ; 11488821 ; 11490253 ; 11492375 ; 11494914 ; 11531975 ; 11534249 ; 12014152 ; 14875224 ; 17389872 ; 22391430 ; 24277714 ; 26611753 ; 26680261 ; 26747275 ; 26747276 ; 26752834 ; 26752835 ; 29214787 ; 29222574 ; 46487913 ; 46506779 ; 47193739 ; 47216755 ; 47440227 ; 47515298 ; 47810733 ; 47885389 ; 48035085
ChEBI ID
ChEBI:47426
CAS Number
54-31-9
TTD Drug ID
D0PQ3G
Formula
C12H11ClN2O5S
Canonical SMILES
C1=COC(=C1)CNC2=CC(=C(C=C2C(=O)O)S(=O)(=O)N)Cl
InChI
1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)
InChIKey
ZZUFCTLCJUWOSV-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
4-chloro-5-sulfamoylanthranilic acid DM002083
76523
Oxidation - N-Dealkylation 1 [4]
Furosemide glucuronide DM002084
21123459
Conjugation - Glucuronidation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001098 Furosemide 4-chloro-5-sulfamoylanthranilic acid Oxidation - N-Dealkylation CYP2E1 [4]
MR001099 Furosemide Furosemide glucuronide Conjugation - Glucuronidation UGT1A1 [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
References
1 Furosemide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effects of cytochrome P450 inducers and inhibitors on the pharmacokinetics of intravenous furosemide in rats: involvement of CYP2C11, 2E1, 3A1 and 3A2 in furosemide metabolism. J Pharm Pharmacol. 2009 Jan;61(1):47-54.
3 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
4 Chemical and enzymatic oxidation of furosemide: formation of pyridinium salts Chem Res Toxicol. 2007 Dec;20(12):1741-4. doi: 10.1021/tx700262z.
5 High-performance liquid chromatographic determination and identification of acyl migration and photodegradation products of furosemide 1-O-acyl glucuronide J Chromatogr B Biomed Sci Appl. 1998 Oct 23;718(1):153-62. doi: 10.1016/s0378-4347(98)00357-0.

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