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

General Information of Drug (ID: DR1388)
Drug Name
Raloxifene
Synonyms
Raloxifene [INN:BAN]; Raloxifeno; Raloxifeno [Spanish]; Raloxifenum; Raloxifenum [Latin]; YX9162EO3I; raloxifene; Keoxifene; LY 139481; LY-139481; Optruma; (2-(4-Hydroxyphenyl)-6-hydroxybenzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)methanone; (6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone; 84449-90-1; C28H27NO4S; CCRIS 7129; CHEBI:8772; CHEMBL81; GZUITABIAKMVPG-UHFFFAOYSA-N; HSDB 7460; RAL; UNII-YX9162EO3I
Indication Osteoporosis [ICD11: FB83] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 473.6 Topological Polar Surface Area 98.2
Heavy Atom Count 34 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5035
PubChem SID
9437 ; 831017 ; 5392969 ; 7890214 ; 7980482 ; 8153100 ; 11111733 ; 11111734 ; 11364773 ; 11367335 ; 11369897 ; 11372937 ; 11375497 ; 11378062 ; 11466890 ; 11468010 ; 11486560 ; 14834427 ; 24277274 ; 26705265 ; 29224106 ; 46506514 ; 46519463 ; 47213213 ; 47365304 ; 47662399 ; 47810849 ; 47810850 ; 48035235 ; 48185088 ; 48259344 ; 48416509 ; 49698670 ; 50065297 ; 50105675 ; 50139488 ; 50898374 ; 53788657 ; 56310724 ; 56312953 ; 56313701 ; 56352882 ; 56427219 ; 57322575 ; 90341181 ; 91148450 ; 92308782 ; 93165668 ; 93166953 ; 96025151
ChEBI ID
CHEBI:8772
CAS Number
84449-90-1
TTD Drug ID
D01XBA
Formula
C28H27NO4S
Canonical SMILES
C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O)C5=CC=C(C=C5)O
InChI
1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2
InChIKey
GZUITABIAKMVPG-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
Raloxifen-4-glucoronide(M2) DM015664
10372066
Conjugation - Glucuronidation 1 [5] , [6] , [7]
Raloxifene-6, 4-diglucuronide(M3) DM018117 N. A. Conjugation - Glucuronidation 1 [5] , [6]
Raloxifene-6-bate-glucuronide(M1) DM015617
10100752
Conjugation - Glucuronidation 1 [5] , [6]
Raloxifene-6-sulfate DM018118 N. A. Unclear - Unclear 1 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010029 Raloxifene Raloxifen-4-glucoronide(M2) Conjugation - Glucuronidation UGT1A1 ... [5], [6], [7]
MR010030 Raloxifene Raloxifene-6-bate-glucuronide(M1) Conjugation - Glucuronidation UGT1A1 ... [5], [6]
MR010031 Raloxifene Raloxifene-6, 4-diglucuronide(M3) Conjugation - Glucuronidation UGT1A1 ... [5], [6]
MR010032 Raloxifene Raloxifene-6-sulfate Unclear - Unclear Unclear [8]
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
[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]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[5]
References
1 Raloxifene was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The role of P-glycoprotein in the bioactivation of raloxifene. Drug Metab Dispos. 2006 Dec;34(12):2073-8.
3 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.
4 Characterization of raloxifene glucuronidation: potential role of UGT1A8 genotype on raloxifene metabolism in vivo. Cancer Prev Res (Phila). 2013 Jul;6(7):719-30.
5 Raloxifene glucuronidation in liver and intestinal microsomes of humans and monkeys: contribution of UGT1A1, UGT1A8 and UGT1A9
6 Determination of raloxifene and its glucuronides in human urine by liquid chromatography-tandem mass spectrometry assay
7 Pharmacokinetics of raloxifene and its clinical application
8 Development and validation of ultra-high-performance liquid chromatography-mass spectrometry method for the determination of raloxifene and its phase II metabolites in plasma: Application to pharmacokinetic studies in rats

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