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

General Information of Drug (ID: DR1940)
Drug Name
Cis-4-hydroxytamoxifen
Synonyms
Afimoxifene, E-isomer; E-4-Hydroxytamoxifen; AKE3PH0IML; SCHEMBL2132301; SCHEMBL640496; ZINC1530090; cis-4-Hydroxytamoxifen; cis/trans-4-Hydroxytamoxifen; (E)-4-Hydroxytamoxifen; (Z)-4-(1-(4-(2-(Dimethylamino)ethoxy)-phenyl)-2-phenylbut-1-en-1-yl)phenol; 174592-47-3; 4-((1E)-1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol; AC1NS1S8; ACM174592473; AKOS015894466; API0000886; BCP9000165; BCP9000243; CHEBI:92076; CHEMBL279301; CP-0071; DTXSID10169854; HY-16950B; UNII-AKE3PH0IML
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 387.5 Topological Polar Surface Area 32.7
Heavy Atom Count 29 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5352135
ChEBI ID
CHEBI:92076
CAS Number
174592-47-3
Formula
C26H29NO2
Canonical SMILES
CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
InChI
1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25+
InChIKey
TXUZVZSFRXZGTL-OCEACIFDSA-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
Cis-4-hydroxytamoxifen-O-glucuronide DM000015
131770036
Conjugation - Glucuronidation 1 [3]
Endoxifen DM000007
10090750
Oxidation - N-demethylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005294 Cis-4-hydroxytamoxifen Cis-4-hydroxytamoxifen-O-glucuronide Conjugation - Glucuronidation UGT1A7 ... [3]
MR005295 Cis-4-hydroxytamoxifen Endoxifen Oxidation - N-demethylation CYP3A5 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[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
[3]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Homo sapiens
UD17_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Km = 0.0074 microM
UD11_HUMAN
[3]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Km = 0.0074 microM
UD18_HUMAN
[3]
References
1 Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants. Breast Cancer Res. 2006;8(4):R50.
2 Tamoxifen dose and serum concentrations of tamoxifen and six of its metabolites in routine clinical outpatient care
3 Glucuronidation of active tamoxifen metabolites by the human UDP glucuronosyltransferases. Drug Metab Dispos. 2007 Nov;35(11):2006-14.

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