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

General Information of Drug (ID: DR0177)
Drug Name
Bazedoxifene
Synonyms
Bazedoxifene; Bazedoxifene [INN]; Bazedoxifeno; Bazedoxifeno [INN-Spanish]; Conbriza; Q16TT9C5BK; TSE-424; WAY 140424; 1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol; 1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol; 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol; 198481-32-2; 1H-Indol-5-ol, 1-[[4-[2-(hexahydro-1H-azepin-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methyl-; C30H34N2O3; CHEMBL46740; UNII-Q16TT9C5BK
Indication Schizophrenia [ICD11: 6A20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 470.6 Topological Polar Surface Area 57.9
Heavy Atom Count 35 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
154257
PubChem SID
5417414 ; 10252039 ; 14907497 ; 46230413 ; 50409595 ; 103224092 ; 103996451 ; 104438324 ; 125669539 ; 129348176 ; 135129358 ; 137115372 ; 142033963 ; 160647805 ; 162810855 ; 163621139 ; 175267431 ; 178103927 ; 179150132 ; 185964861 ; 198992700 ; 204379955 ; 223780042 ; 226426848 ; 251971047 ; 252434487 ; 252477814
ChEBI ID
CHEBI:135947
CAS Number
198481-32-2
TTD Drug ID
D0JY8T
Formula
C30H34N2O3
Canonical SMILES
CC1=C(N(C2=C1C=C(C=C2)O)CC3=CC=C(C=C3)OCCN4CCCCCC4)C5=CC=C(C=C5)O
InChI
1S/C30H34N2O3/c1-22-28-20-26(34)12-15-29(28)32(30(22)24-8-10-25(33)11-9-24)21-23-6-13-27(14-7-23)35-19-18-31-16-4-2-3-5-17-31/h6-15,20,33-34H,2-5,16-19,21H2,1H3
InChIKey
UCJGJABZCDBEDK-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
Bazedoxifene-4'-glucuronide DM001618
71313640
Conjugation - Glucuronidation 1 [3]
Bazedoxifene-5-glucuronide DM001617
9895767
Conjugation - Glucuronidation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000349 Bazedoxifene Bazedoxifene-5-glucuronide Conjugation - Glucuronidation UGT1A1 ... [3]
MR000350 Bazedoxifene Bazedoxifene-4'-glucuronide Conjugation - Glucuronidation UGT1A1 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-glucuronidase (uidA) DME1025 Lactobacillus gasseri
Q9AHJ8_LACGS
3.2.1.31
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[5]
References
1 ClinicalTrials.gov (NCT04113993) Bazedoxifene -Treatment for Women With Schizophrenia.
2 Long-term administration of conjugated estrogen and bazedoxifene decreased murine fecal beta-glucuronidase activity without impacting overall microbiome community. Sci Rep. 2018 May 25;8(1):8166.
3 UGT1A1*28 polymorphism influences glucuronidation of bazedoxifene. Pharmazie. 2015 Feb;70(2):94-6.
4 In vitro metabolism, permeability, and efflux of bazedoxifene in humans. Drug Metab Dispos. 2010 Sep;38(9):1471-9.
5 UGT1A1*28 polymorphism influences glucuronidation of bazedoxifene Pharmazie. 2015 Feb;70(2):94-6.

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