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

General Information of Drug (ID: DR0777)
Drug Name
Glimepiride
Synonyms
Glimepirid; Glimepirida; Glimepirida [Spanish]; Glimepiridum; Glimepiridum [Latin]; Glimepride; Glista OD; cis-Glimepiride; glimepiride; 1-((p-(2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl)phenyl)sulfonyl)-3-(trans-4-methylcyclohexyl)urea; Amarel; Amaryl; Endial; GLIMPERIDE; 24T6XIR2MZ; 684286-46-2; 6KY687524K; 93479-97-1; BRN 5365754; CCRIS 7083; CHEBI:5383; HOE 490; Hoe-490; MFCD00878417; UNII-24T6XIR2MZ; UNII-6KY687524K
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 490.6 Topological Polar Surface Area 133
Heavy Atom Count 34 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3476
PubChem SID
9871 ; 5043708 ; 7847659 ; 7979409 ; 8145852 ; 8152210 ; 11112876 ; 11466679 ; 11467799 ; 11486338 ; 12013623 ; 14908413 ; 24895093 ; 26719876 ; 26755029 ; 26755030 ; 29222609 ; 32963623 ; 46386690 ; 46508842 ; 47589079 ; 47959862 ; 48155569 ; 48185080 ; 48334594 ; 49648856 ; 49699123 ; 49731995 ; 49835734 ; 50037704 ; 50126308 ; 56313637 ; 57321825 ; 77374551 ; 81040871 ; 81092812 ; 85787655 ; 85787837 ; 91613422 ; 92125647 ; 92308643 ; 92309214 ; 92711714 ; 99344865 ; 99437102 ; 103394534 ; 103543151 ; 103913636 ; 104171333 ; 104303626
ChEBI ID
ChEBI:5383
CAS Number
93479-97-1
TTD Drug ID
D0B2GI
Formula
C24H34N4O5S
Canonical SMILES
CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
InChI
1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19-
InChIKey
WIGIZIANZCJQQY-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
Cyclohexyl hydroxymethyl glimepiride DM002126
130939
Oxidation - Hydroxylation 1 [3] , [4]
Cyclohexyl carboxyl glimepiride DM002127
10075365
Oxidation - Oxidation 2 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001140 Glimepiride Cyclohexyl hydroxymethyl glimepiride Oxidation - Hydroxylation CYP2C9 [3], [4]
MR001139 Cyclohexyl hydroxymethyl glimepiride Cyclohexyl carboxyl glimepiride Oxidation - Oxidation Unclear [3], [4]
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]
References
1 Glimepiride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of CYP2C9 genetic polymorphisms on the efficacy and pharmacokinetics of glimepiride in subjects with type 2 diabetes. Diabetes Res Clin Pract. 2006 May;72(2):148-54.
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 glimepiride and its metabolites in human plasma by liquid chromatography coupled to a tandem mass spectrometry Arch Pharm Res. 2011 Dec;34(12):2073-8. doi: 10.1007/s12272-011-1210-0.

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