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

General Information of Drug (ID: DR0677)
Drug Name
Ezetimibe
Synonyms
Ezetimibe; Ezetimibe (Zetia); Ezetrol; SCH-58235; Sch 58235; (-)-Sch 58235; (3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one; EOR26LQQ24; Ezedoc; (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one; 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone; 163222-33-1; CHEBI:49040; DSSTox_CID_24223; DSSTox_GSID_44223; DSSTox_RID_80127; UNII-EOR26LQQ24; Zetia
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 409.4 Topological Polar Surface Area 60.8
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
150311
PubChem SID
7849028 ; 10250673 ; 11528896 ; 12014979 ; 14879623 ; 14928749 ; 26719841 ; 46226990 ; 46386640 ; 46507625 ; 49681809 ; 49693660 ; 50539938 ; 53787196 ; 57347010 ; 71821424 ; 81146074 ; 92308446 ; 92718207 ; 103326446 ; 104179182 ; 104253290 ; 104428106 ; 117884262 ; 124658886 ; 124757411 ; 124801398 ; 125164215 ; 126592989 ; 126621626 ; 126653456 ; 126667079 ; 127315811 ; 127315812 ; 127315813 ; 127315814 ; 127315815 ; 127315816 ; 127315817 ; 127315818 ; 127315819 ; 127315820 ; 127315821 ; 127315822 ; 127315823 ; 127315824 ; 128826430 ; 131854738 ; 134338005 ; 135107180
ChEBI ID
ChEBI:49040
CAS Number
163222-33-1
TTD Drug ID
D09LWS
Formula
C24H21F2NO3
Canonical SMILES
C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)O
InChI
1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1
InChIKey
OLNTVTPDXPETLC-XPWALMASSA-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
Benzylic glucuronide SCH 488128 DM000137 N. A. Oxidation - Oxidation 1 [2]
Ezetimibe-glucuronide DM000136 N. A. Conjugation - Glucuronidation 1 [2] , [5] , [6] , [7]
SCH 57871 DM000135
9801494
Conjugation - Glucuronidation 1 [2]
ACP-5461 DM000053 N. A. Oxidation - Oxidation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001007 Ezetimibe SCH 57871 Conjugation - Glucuronidation Unclear [2]
MR001008 Ezetimibe Ezetimibe-glucuronide Conjugation - Glucuronidation UGT1A1 ... [2], [5], [6], [7]
MR001009 Ezetimibe Benzylic glucuronide SCH 488128 Oxidation - Oxidation Unclear [2]
MR001006 SCH 57871 ACP-5461 Oxidation - Oxidation Unclear [2]
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]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
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) DME1379 Bacteroides stercoris Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
⏷ Show the Full List of 13  DME(s)
References
1 Ezetimibe was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94.
3 Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Bioequivalence Study of Ezetimibe Tablets After a Single Oral Dose of 10?mg in Healthy Japanese Subjects Under Fasting Conditions. Clin Pharmacol Drug Dev. 2023 Apr 6. doi: 10.1002/cpdd.1245.
6 Pharmacokinetics and bioequivalence of Ezetimibe tablet versus Ezetrol?:an open-label, randomized, two-sequence crossover study in healthy Chinese subjects. BMC Pharmacol Toxicol. 2023 Feb 3;24(1):7. doi: 10.1186/s40360-023-00649-y.
7 Investigation of the discriminatory ability of analytes for the bioequivalence assessment of ezetimibe: Parent drug, metabolite, total form, and combination of parent drug and total form. Eur J Pharm Sci. 2022 Jul 1;174:106192. doi: 10.1016/j.ejps.2022.106192.

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