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Estrogen receptor Cytochrome P450 3A4 Cytochrome P450 2D6 Cytochrome P450 2B6 UDP- glucuronosyltransferase 1-4 Dimethylaniline monooxygenase [N-oxide- forming] 3 Dimethylaniline monooxygenase [N-oxide- forming] 1 Cytochrome P450 3A4 Cytochrome P450 2D6 UDP- glucuronosyltransferase 1-4 UDP- glucuronosyltransferase 1-4 Sulfotransferase 1A1 Cytochrome P450 3A4 Cytochrome P450 3A5 Cytochrome P450 3A4 Cytochrome P450 3A5 Cytochrome P450 2D6 UDP- glucuronosyltransferase 1-10 Cytochrome P450 3A4 Cytochrome P450 3A4 Sulfotransferase 1A1 Endoxifen 4-Hydroxytamoxifen α-Hydroxytamoxifen α-Hydroxy-tamoxifen-O- glucuronide Endoxifen Norendoxifen Tamoxifen NADPH H+ O2 H2O NADP NADPH H+ O2 4'-Hydroxytamoxifen H2O NADP Uridine diphosphate glucuronic acid Tamoxifen-N-glucuronide Uridine 5'-diphosphate NADPH H+ O2 Tamoxifen N-oxide NADP H2O H2O NADP O2 NADPH H+ NADPH H+ O2 4-Hydroxytamoxifen NADP H2O Uridine diphosphate glucuronic acid 4-Hydroxytamoxifen-O- glucuronide Uridine 5'-diphosphate Uridine diphosphate glucuronic acid 4-Hydroxytamoxifen-N- glucuronide Uridine 5'-diphosphate Phosphoadenosine phosphosulfate 4-Hydroxytamoxifen sulfate Adenosine 3',5'- diphosphate O2 NADPH H+ N-Desmethyltamoxifen H2O Formaldehyde NADP O2 NADPH H+ H2O Formaldehyde NADP NADPH H+ O2 H2O NADP Uridine diphosphate glucuronic acid Endoxifen O-glucuronide Uridine 5'-diphosphate O2 NADPH H+ α-Hydroxy-N-desmethyl- tamoxifen H2O NADP O2 NADPH H+ N,N-Didesmethyltamoxifen H2O NADP Formaldehyde Phosphoadenosine phosphosulfate Endoxifen sulfate Adenosine 3',5'- diphosphate Heme Heme Heme FAD FAD Heme Heme Heme Heme Heme Heme Heme Heme Heme Hepatocyte Breast Cancer Cell Endoplasmic Reticulum Membrane
Endoplasmic Reticulum ESR1 CYP3A4 CYP2D6 CYP2B6 UGT1A4 FMO3 FMO1 CYP3A4 CYP2D6 UGT1A4 UGT1A4 SULT1A1 CYP3A4 CYP3A5 CYP3A4 CYP3A5 CYP2D6 UGT1A10 CYP3A4 CYP3A4 SULT1A1 Endoxifen 4- Hydroxytamoxifen α- Hydroxytamoxifen α-Hydroxy- tamoxifen-O- glucuronide Endoxifen Norendoxifen Tamoxifen NADPH Hydrogen Ion Oxygen Water NADP NADPH Hydrogen Ion Oxygen 4'- Hydroxytamoxifen Water NADP Uridine diphosphate glucuronic acid Tamoxifen-N- glucuronide Uridine 5'-diphosphate NADPH Hydrogen Ion Oxygen Tamoxifen N-oxide NADP Water Water NADP Oxygen NADPH Hydrogen Ion NADPH Hydrogen Ion Oxygen 4- Hydroxytamoxifen NADP Water Uridine diphosphate glucuronic acid 4- Hydroxytamoxifen- O-glucuronide Uridine 5'-diphosphate Uridine diphosphate glucuronic acid 4- Hydroxytamoxifen- N-glucuronide Uridine 5'-diphosphate Phosphoadenosine phosphosulfate 4- Hydroxytamoxifen sulfate Adenosine 3',5'- diphosphate Oxygen NADPH Hydrogen Ion N- Desmethyltamoxifen Water Formaldehyde NADP Oxygen NADPH Hydrogen Ion Water Formaldehyde NADP NADPH Hydrogen Ion Oxygen Water NADP Uridine diphosphate glucuronic acid Endoxifen O-glucuronide Uridine 5'-diphosphate Oxygen NADPH Hydrogen Ion α-Hydroxy-N- desmethyl- tamoxifen Water NADP Oxygen NADPH Hydrogen Ion N,N- Didesmethyltamoxifen Water NADP Formaldehyde Phosphoadenosine phosphosulfate Endoxifen sulfate Adenosine 3',5'- diphosphate
ESR1 CYP3A4 CYP2D6 CYP2B6 UGT1A4 FMO3 FMO1 CYP3A4 CYP2D6 UGT1A4 UGT1A4 SULT1A1 CYP3A4 CYP3A5 CYP3A4 CYP3A5 CYP2D6 UGT1A10 CYP3A4 CYP3A4 SULT1A1 Endoxfn 4-Htmfn aHtfen αHTOG Endoxfn Norendo Tamoxif NADPH H+ O2 H2O NADP NADPH H+ O2 4'-Htmf H2O NADP UDPGlcA TamfNGl UDP NADPH H+ O2 TamfNOx NADP H2O H2O NADP O2 NADPH H+ NADPH H+ O2 4-Htmfn NADP H2O UDPGlcA 4HafOGl UDP UDPGlcA 4HafNGl UDP Paps 4HafSO A3'5'PP O2 NADPH H+ NDesmf H2O Formol NADP O2 NADPH H+ H2O Formol NADP NADPH H+ O2 H2O NADP UDPGlcA EndoFoG UDP O2 NADPH H+ αHNDT H2O NADP O2 NADPH H+ NNDidt H2O NADP Formol Paps EndfSO A3'5'PP Heme Heme Heme FAD FAD Heme Heme Heme Heme Heme Heme Heme Heme Heme Hepatocyte Breast Cancer Cell Endoplasmic Reticulum Membrane
Endoplasmic Reticulum ESR1 CYP3A4 CYP2D6 CYP2B6 UGT1A4 FMO3 FMO1 CYP3A4 CYP2D6 UGT1A4 UGT1A4 SULT1A1 CYP3A4 CYP3A5 CYP3A4 CYP3A5 CYP2D6 UGT1A10 CYP3A4 CYP3A4 SULT1A1 Endoxfn 4-Htmfn aHtfen αHTOG Endoxfn Norendo Tamoxif NADPH H+ O2 H2O NADP NADPH H+ O2 4'-Htmf H2O NADP UDPGlcA TamfNGl UDP NADPH H+ O2 TamfNOx NADP H2O H2O NADP O2 NADPH H+ NADPH H+ O2 4-Htmfn NADP H2O UDPGlcA 4HafOGl UDP UDPGlcA 4HafNGl UDP Paps 4HafSO A3'5'PP O2 NADPH H+ NDesmf H2O Formol NADP O2 NADPH H+ H2O Formol NADP NADPH H+ O2 H2O NADP UDPGlcA EndoFoG UDP O2 NADPH H+ αHNDT H2O NADP O2 NADPH H+ NNDidt H2O NADP Formol Paps EndfSO A3'5'PP