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

General Information of Drug (ID: DR0868)
Drug Name
Indapamide
Synonyms
Indaflex; Indamol; Indapamida; Indapamida [INN-Spanish]; Indapamide (Lozol); Indapamidum; Indapamidum [INN-Latin]; Ipamix; Metindamide; Natrilix; Noranat; Pressurai; RHC 2555; S-1520; SE 1520; SE-1520; Tandix; Tertensif; USV 2555; Arifon; Bajaten; Cormil; Damide; Fludex; Veroxil; indapamide; 1-(4-Chloro-3-sulfamoylbenzamido)-2-methylindoline; 26807-65-8; 4-Chloro-N-(2-methyl-1-indolinyl)-3-sulfamoylbenzamide; BRN 1604026; Benzamide, 3-(aminosulfonyl)-4-chloro-N-(2,3-dihydro-2-methyl-1H-indol-1-yl)-; EINECS 248-012-7; Lozol; MFCD00079375
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 365.8 Topological Polar Surface Area 101
Heavy Atom Count 24 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3702
PubChem SID
855885 ; 7548663 ; 7847411 ; 7979602 ; 8149386 ; 8152339 ; 11335683 ; 11360922 ; 11363811 ; 11366373 ; 11368935 ; 11371494 ; 11373532 ; 11377097 ; 11461894 ; 11484755 ; 11488796 ; 11490283 ; 11491832 ; 11494731 ; 14828553 ; 24895952 ; 26611782 ; 26680433 ; 26747199 ; 26747200 ; 29222825 ; 46508626 ; 47216741 ; 47515281 ; 48184956 ; 48259190 ; 48259191 ; 48334450 ; 49698709 ; 49832093 ; 49876093 ; 56413189 ; 56422467 ; 57321947 ; 57654295 ; 80156605 ; 80953761 ; 85086931 ; 85148358 ; 85788440 ; 87561081 ; 92124043 ; 92307457 ; 92309252
ChEBI ID
CHEBI:5893
CAS Number
26807-65-8
TTD Drug ID
D0H8FH
Formula
C16H16ClN3O3S
Canonical SMILES
CC1CC2=CC=CC=C2N1NC(=O)C3=CC(=C(C=C3)Cl)S(=O)(=O)N
InChI
1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23)
InChIKey
NDDAHWYSQHTHNT-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
Indapamide epoxide intermediate DM000970 N. A. Oxidation - Oxidation 1 [2]
Indapamide metabolite M1 DM000965
196806
Oxidation - Oxidation 1 [2] , [4]
Indapamide metabolite M5 DM000968 N. A. Oxidation - Oxidation 1 [2]
Indapamide glutathione conjugate M7 DM000971 N. A. Conjugation - Glutathione Conjugation 2 [2]
Indapamide metabolite M3 DM000966 N. A. Oxidation - Oxidation 2 [2]
Indapamide metabolite M4 DM000969 N. A. Oxidation - Oxidation 2 [2]
Indapamide metabolite M6 DM000972 N. A. Oxidation - Dihydroxylation 2 [2]
Indapamide metabolite M2 DM000967 N. A. Oxidation - Oxidation 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001182 Indapamide Indapamide metabolite M1 Oxidation - Oxidation CYP3A4 [2], [4]
MR001183 Indapamide Indapamide metabolite M5 Oxidation - Oxidation CYP3A4 [2]
MR001184 Indapamide Indapamide epoxide intermediate Oxidation - Oxidation CYP3A4 [2]
MR001180 Indapamide epoxide intermediate Indapamide glutathione conjugate M7 Conjugation - Glutathione Conjugation Unclear [2]
MR001181 Indapamide epoxide intermediate Indapamide metabolite M6 Oxidation - Dihydroxylation Unclear [2]
MR001176 Indapamide metabolite M1 Indapamide metabolite M3 Oxidation - Oxidation CYP3A4 [2]
MR001178 Indapamide metabolite M5 Indapamide metabolite M4 Oxidation - Oxidation CYP3A4 [2]
MR001177 Indapamide metabolite M3 Indapamide metabolite M2 Oxidation - Oxidation CYP3A4 [2]
MR001179 Indapamide metabolite M4 Indapamide metabolite M2 Oxidation - Oxidation CYP3A4 [2]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
References
1 Indapamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Dehydrogenation of the indoline-containing drug 4-chloro-N-(2-methyl-1-indolinyl)-3-sulfamoylbenzamide (indapamide) by CYP3A4: correlation with in silico predictions. Drug Metab Dispos. 2009 Mar;37(3):672-84.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Vasorelaxant actions of 5-OH-indapamide, a major metabolite of indapamide: comparison with indapamide, hydrochlorothiazide and cicletanine Eur J Pharmacol. 1994 Apr 21;256(2):185-91. doi: 10.1016/0014-2999(94)90244-5.

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