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

General Information of Drug (ID: DR0778)
Drug Name
Glipizide
Synonyms
Glibenese; Glibetin; Glican; Glidiab; Glipid; Glipizida; Glipizida [INN-Spanish]; Glipizide (Glucotrol); Glipizidum; Glipizidum [INN-Latin]; Gluco-Rite; Glucolip; Glucotrol; Glucotrol XL; Glucozide; Glupitel; Glupizide; Glydiazinamide; Aldiab; Digrin; Dipazide; K 4024; K-4024; Melizide; Metaglip; Mindiab; Minidab; Minidiab; Minodiab; Napizide; Ozidia; Sucrazide; TK 1320; X7WDT95N5C; glipizide; 29094-61-9; BRN 0903495; C21H27N5O4S; CHEMBL1073; CP 28,720; CP 28720; CP-28720; EINECS 249-427-6; Glide; Glyde; MFCD00072159; UNII-X7WDT95N5C
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 445.5 Topological Polar Surface Area 139
Heavy Atom Count 31 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
3478
PubChem SID
855947 ; 3153201 ; 5043710 ; 7847401 ; 7979413 ; 8152212 ; 10321342 ; 11111214 ; 11112714 ; 11119955 ; 11120443 ; 11120931 ; 11121414 ; 11121894 ; 11147038 ; 11362483 ; 11365045 ; 11367607 ; 11370237 ; 11370238 ; 11373208 ; 11375769 ; 11466159 ; 11467279 ; 11485877 ; 14906210 ; 17405183 ; 24277839 ; 24858438 ; 25819918 ; 26751569 ; 26751570 ; 29222611 ; 46505865 ; 47290874 ; 47290875 ; 47515059 ; 47588733 ; 47662000 ; 47810481 ; 47885136 ; 49698363 ; 49836250 ; 50060598 ; 50100247 ; 50104189 ; 50104190 ; 50104191 ; 53777727 ; 53787230
ChEBI ID
CHEBI:5384
CAS Number
29094-61-9
TTD Drug ID
D0Z4SB
Formula
C21H27N5O4S
Canonical SMILES
CC1=CN=C(C=N1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
InChI
1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)
InChIKey
ZJJXGWJIGJFDTL-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
3-cis-hydroxyglipizide DM002128
131769998
Oxidation - Hydroxylation 1 [7] , [8]
3-trans-hydroxyglipizide DM002130 N. A. Oxidation - Hydroxylation 1 [8]
4-trans-hydroxyglipizide DM002129 N. A. Oxidation - Hydroxylation 1 [7] , [8]
4-trans-OH-glipizide DM002131 N. A. Oxidation - Hydroxylation 1 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001141 Glipizide 3-cis-hydroxyglipizide Oxidation - Hydroxylation CYP2C9 [7], [8]
MR001142 Glipizide 4-trans-hydroxyglipizide Oxidation - Hydroxylation CYP2C9 [7], [8]
MR001143 Glipizide 3-trans-hydroxyglipizide Oxidation - Hydroxylation CYP2C9 [8]
MR001144 Glipizide 4-trans-OH-glipizide Oxidation - Hydroxylation CYP2C9 [9]
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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
⏷ Show the Full List of 9  DME(s)
References
1 Glipizide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical consequences of cytochrome P450 2C9 polymorphisms. Clin Pharmacol Ther. 2005 Jan;77(1):1-16.
3 Repaglinide : a pharmacoeconomic review of its use in type 2 diabetes mellitus. Pharmacoeconomics. 2004;22(6):389-411.
4 Pharmacokinetics of chlorpheniramine, phenytoin, glipizide and nifedipine in an individual homozygous for the CYP2C9*3 allele. Pharmacogenetics. 1999 Feb;9(1):71-80.
5 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.
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 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.
8 Simultaneous determination of glipizide and its four hydroxylated metabolites in human urine using LC-MS/MS and its application in urinary phenotype study J Pharm Biomed Anal. 2017 May 30;139:179-186. doi: 10.1016/j.jpba.2017.03.005.
9 U. S. FDA Label -Glipizide

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