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

General Information of Drug (ID: DR1404)
Drug Name
Repaglinide
Synonyms
Repaglinida; Repaglinida [INN-Spanish]; Repaglinide; Repaglinidum; Repaglinidum [INN-Latin]; GlucoNorm; NovoNorm; Prandin; (S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid; (S)-2-Ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid; 135062-02-1; 668Z8C33LU; AG-EE 388 ZW; AG-EE 623 ZW; AG-EE 623ZW; AGEE-623ZW; C27H36N2O4; CHEBI:8805; CHEMBL1272; MFCD00906179; UNII-668Z8C33LU
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 452.6 Topological Polar Surface Area 78.9
Heavy Atom Count 33 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
65981
PubChem SID
9872 ; 7847660 ; 7980507 ; 8190080 ; 11112894 ; 11467074 ; 11468194 ; 11486642 ; 12014667 ; 14808699 ; 14833410 ; 24724596 ; 26719812 ; 43122707 ; 46386564 ; 46508150 ; 47425572 ; 48244693 ; 48319772 ; 48395177 ; 48416511 ; 49648522 ; 49699266 ; 49888451 ; 50100536 ; 52108264 ; 53789672 ; 57315871 ; 81092844 ; 85788088 ; 92125938 ; 92308165 ; 92308498 ; 92719265 ; 93166496 ; 99218180 ; 99431925 ; 99437146 ; 103394824 ; 103914669 ; 104041348 ; 104179029 ; 104335174 ; 117545849 ; 117873275 ; 121363609 ; 124659000 ; 124757239 ; 124799919 ; 125164043
ChEBI ID
CHEBI:8805
CAS Number
135062-02-1
TTD Drug ID
D0N5YA
Formula
C27H36N2O4
Canonical SMILES
CCOC1=C(C=CC(=C1)CC(=O)NC(CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)O
InChI
1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1
InChIKey
FAEKWTJYAYMJKF-QHCPKHFHSA-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
Hydroxyrepaglinide DM016115
46781896
Oxidation - Hydroxylation 1 [5]
Repaglinide M0-OH DM016183
57347719
Oxidation - Hydroxylation 1 [3]
Repaglinide M1 DM016059
29977666
Oxidation - Oxidation 1 [5] , [6]
Repaglinide M2 DM016060
29977672
Unclear - Unclear 1 [5] , [6]
Repaglinide M5 DM016002
22132924
Unclear - Unclear 1 [3]
Repaglinide M7 DM016335
71751995
Conjugation - Glucuronidation 1 [3]
Repaglinide M1 DM016059
29977666
Oxidation - Oxidation 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013049 Repaglinide Repaglinide M2 Unclear - Unclear CYP3A4 ... [5], [6]
MR013051 Repaglinide Hydroxyrepaglinide Oxidation - Hydroxylation CYP3A4 ... [5]
MR013052 Repaglinide Repaglinide M1 Oxidation - Oxidation CYP3A4 ... [5], [6]
MR013053 Repaglinide Repaglinide M5 Unclear - Unclear CYP3A4 ... [3]
MR013054 Repaglinide Repaglinide M7 Conjugation - Glucuronidation UGT1A1 ... [3]
MR013055 Repaglinide Repaglinide M0-OH Oxidation - Hydroxylation CYP3A4 ... [3]
MR013050 Repaglinide M2 Repaglinide M1 Oxidation - Oxidation Unclear [5]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[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) DME1256 Bacteroides sartorii 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) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
⏷ Show the Full List of 11  DME(s)
References
1 Repaglinide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Drug-drug and food-drug pharmacokinetic interactions with new insulinotropic agents repaglinide and nateglinide. Clin Pharmacokinet. 2007;46(2):93-108.
3 Repaglinide-gemfibrozil drug interaction: inhibition of repaglinide glucuronidation as a potential additional contributing mechanism. Br J Clin Pharmacol. 2010 Dec;70(6):870-80.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Different effects of SLCO1B1 polymorphism on the pharmacokinetics and pharmacodynamics of repaglinide and nateglinide
6 Bioanalytical method for in vitro metabolism study of repaglinide using 96-blade thin-film solid-phase microextraction and LC-MS/MS

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