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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
+
O
2
H
2
O
NADP
NADPH
H
+
O
2
4'-Hydroxytamoxifen
H
2
O
NADP
Uridine
diphosphate
glucuronic acid
Tamoxifen-N-glucuronide
Uridine
5'-diphosphate
NADPH
H
+
O
2
Tamoxifen N-oxide
NADP
H
2
O
H
2
O
NADP
O
2
NADPH
H
+
NADPH
H
+
O
2
4-Hydroxytamoxifen
NADP
H
2
O
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
O
2
NADPH
H
+
N-Desmethyltamoxifen
H
2
O
Formaldehyde
NADP
O
2
NADPH
H
+
H
2
O
Formaldehyde
NADP
NADPH
H
+
O
2
H
2
O
NADP
Uridine
diphosphate
glucuronic acid
Endoxifen O-glucuronide
Uridine
5'-diphosphate
O
2
NADPH
H
+
α-Hydroxy-N-desmethyl-
tamoxifen
H
2
O
NADP
O
2
NADPH
H
+
N,N-Didesmethyltamoxifen
H
2
O
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