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

General Information of Drug (ID: DR0776)
Drug Name
Gliclazide
Synonyms
Gliclazida; Gliclazida [INN-Spanish]; Gliclazidum; Gliclazidum [INN-Latin]; Glimicron; Diamicron; Nordialex; gliclazide; 1-(3-Azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea; 1-(3-Azabicyclo[3.3.0]oct-3-yl)-3-p-tolylsulphonylurea; 1-(Hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea; 21187-98-4; C15H21N3O3S; CHEBI:31654; MFCD00409893; N-(4-Methylbenzenesulfonyl)-N'-(3-azabicyclo(3.3.0)oct-3-yl)urea; N-(hexahydrocyclopenta[c]pyrrol-2(1H)-ylcarbamoyl)-4-methylbenzenesulfonamide
Indication Diabetes mellitus [ICD11: 5A10] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 323.4 Topological Polar Surface Area 86.9
Heavy Atom Count 22 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3475
PubChem SID
3206372 ; 5035155 ; 7848662 ; 7979407 ; 8152209 ; 10321809 ; 11342141 ; 11362324 ; 11364372 ; 11366934 ; 11369496 ; 11372903 ; 11374235 ; 11377658 ; 11466586 ; 11467706 ; 11486292 ; 11487726 ; 11491677 ; 11492413 ; 11495292 ; 11533945 ; 14826273 ; 24895090 ; 26612635 ; 26612723 ; 26748918 ; 26748919 ; 26748920 ; 29222608 ; 47656599 ; 47730748 ; 48179242 ; 48179243 ; 48328563 ; 48403959 ; 48416054 ; 49646130 ; 49698833 ; 50061218 ; 50086570 ; 50107481 ; 50107482 ; 50107483 ; 50880518 ; 57321824 ; 81040947 ; 81066070 ; 81093129 ; 85280584
ChEBI ID
ChEBI:31654
CAS Number
21187-98-4
TTD Drug ID
D0M2MR
Formula
C15H21N3O3S
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2
InChI
1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)
InChIKey
BOVGTQGAOIONJV-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
6-OH-gliclazide DM006700 N. A. Oxidation - Hydrolyzationn 1 [2] , [5]
7-OH-gliclazide DM006698 N. A. Oxidation - Hydrolyzationn 1 [2] , [5]
Methylhydroxygliclazide DM006696
192219
Oxidation - Hydrolyzationn 1 [2] , [5]
6-OH-gliclazide glucuronide DM006701 N. A. Conjugation - Glucuronidation 2 [5]
7-OH-gliclazide glucuronide DM006699 N. A. Conjugation - Glucuronidation 2 [5]
Carboxygliclazide DM006697 N. A. Oxidation - Oxidationn 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007223 Gliclazide Methylhydroxygliclazide Oxidation - Hydrolyzationn CYP2C9 ... [2], [5]
MR007225 Gliclazide 7-OH-gliclazide Oxidation - Hydrolyzationn CYP2C9 [2], [5]
MR007227 Gliclazide 6-OH-gliclazide Oxidation - Hydrolyzationn CYP2C9 [2], [5]
MR007228 6-OH-gliclazide 6-OH-gliclazide glucuronide Conjugation - Glucuronidation Unclear [5]
MR007226 7-OH-gliclazide 7-OH-gliclazide glucuronide Conjugation - Glucuronidation Unclear [5]
MR007224 Methylhydroxygliclazide Carboxygliclazide Oxidation - Oxidationn Unclear [5]
⏷ 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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [4]
⏷ Show the Full List of 8  DME(s)
References
1 ClinicalTrials.gov (NCT00738088) Variation in Sulphonylurea Response in Type 2 Diabetes.
2 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.
3 The metabolism of CYP2C9 and CYP2C19 for gliclazide by homology modeling and docking study. Eur J Med Chem. 2009 Feb;44(2):854-61.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 The metabolism of gliclazide in man

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