Details of the Metabolic Reaction (MR)

General Information of This Metabolic Reaction (MR) (ID: MR002650)
Formula
CYP3A5 ...
SVG example
4-Hydroxylation
Reactant Estradiol Product 4-hydroxyestrone
Reactant Info Product Info
Metabolic Enzyme Cytochrome P450 3A5 (CYP3A5) DME Info
Cytochrome P450 1B1 (CYP1B1) DME Info
Metabolic Type Oxidation - 4-Hydroxylation
Other MR(s) Related to The Reactant of This MR
Other MR(s) That Produce The Reactant of This MR
MR ID Reactant Product MR Type Related Drug REF
MR002644 Estradiol acetate Estradiol Hydrolysis - Esterase Hydrolysis Estradiol acetate [1]
MR002667 Estradiol cypionate Estradiol Hydrolysis - Esterase Hydrolysis Estradiol cypionate [1]
MR002690 Estradiol cypionate Estradiol Hydrolysis - Esterase Hydrolysis Estradiol valerate [1]
MR000958 Estramustine Estradiol Unclear Estramustine [2], [3]
MR004243 Estrone sulfate Estradiol-17 beta Unclear Estrone sulfate [4]
MR003145 4-androstene-3,17-dione(AD) Estradiol-17 beta Unclear Dehydroepiandrosterone [5]
MR003148 Testosterone Estradiol-17 beta Unclear Dehydroepiandrosterone [5]
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Other MR(s) That Metabolize The Reactant of This MR
MR ID Reactant Product MR Type Related Drug REF
MR002634 Estradiol 17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide) Unclear Estradiol acetate [6]
MR002658 Estradiol 17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide) Unclear Estradiol cypionate [6]
MR002681 Estradiol 17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide) Unclear Estradiol valerate [6]
MR002631 Estradiol 17-beta-Estradiol glucuronide Unclear Estradiol acetate [6], [7]
MR002655 Estradiol 17-beta-Estradiol glucuronide Unclear Estradiol cypionate [6]
MR002678 Estradiol 17-beta-Estradiol glucuronide Unclear Estradiol valerate [6]
MR002630 Estradiol 17-beta-Estradiol-3-glucuronide Unclear Estradiol acetate [6]
MR002653 Estradiol 17-beta-Estradiol-3-glucuronide Unclear Estradiol cypionate [6]
MR002676 Estradiol 17-beta-Estradiol-3-glucuronide Unclear Estradiol valerate [6]
MR002632 Estradiol 17alpha-Estradiol-3-glucuronide Unclear Estradiol acetate [6]
MR002656 Estradiol 17alpha-Estradiol-3-glucuronide Unclear Estradiol cypionate [6]
MR002679 Estradiol 17alpha-Estradiol-3-glucuronide Unclear Estradiol valerate [6]
MR002624 Estradiol 17beta-Estradiol-3,17-beta-sulfate Unclear Estradiol acetate [8]
MR002647 Estradiol 17beta-Estradiol-3,17-beta-sulfate Unclear Estradiol cypionate [8]
MR002670 Estradiol 17beta-Estradiol-3,17-beta-sulfate Unclear Estradiol valerate [8]
MR002625 Estradiol 2-hydroxyestrone Oxidation - 2-Hydroxylation Estradiol acetate [6], [9]
MR002648 Estradiol 2-hydroxyestrone Oxidation - Hydroxylation Estradiol cypionate [6], [9]
MR002671 Estradiol 2-hydroxyestrone Oxidation - Hydroxylation Estradiol valerate [6], [9]
MR002654 Estradiol 2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) Unclear Estradiol cypionate [6], [7]
MR002677 Estradiol 2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) Unclear Estradiol valerate [6], [7]
MR002635 Estradiol 2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) metabolite Unclear Estradiol acetate [6]
MR002629 Estradiol 2-Methoxyestrone 3-glucuronide Unclear Estradiol acetate [6]
MR002652 Estradiol 2-Methoxyestrone 3-glucuronide Unclear Estradiol cypionate [6]
MR002675 Estradiol 2-Methoxyestrone 3-glucuronide Unclear Estradiol valerate [6]
MR002626 Estradiol 4-hydroxyestradiol Unclear Estradiol acetate [9]
MR002649 Estradiol 4-hydroxyestradiol Oxidation - Hydroxylation Estradiol cypionate [9]
MR002672 Estradiol 4-hydroxyestradiol Oxidation - Hydroxylation Estradiol valerate [9]
MR002633 Estradiol Estradiol-17alpha 3-D-glucuronoside Unclear Estradiol acetate [6]
MR002657 Estradiol Estradiol-17alpha 3-D-glucuronoside Unclear Estradiol cypionate [6]
MR002680 Estradiol Estradiol-17alpha 3-D-glucuronoside Unclear Estradiol valerate [6]
MR002628 Estradiol Estradiol-17beta 3-sulfate Unclear Estradiol acetate [10]
MR002651 Estradiol Estradiol-17beta 3-sulfate Unclear Estradiol cypionate [10]
MR002674 Estradiol Estradiol-17beta 3-sulfate Unclear Estradiol valerate [10]
MR002636 Estradiol Estrone Unclear Estradiol acetate [11]
MR002659 Estradiol Estrone Unclear Estradiol cypionate [11]
MR002682 Estradiol Estrone Unclear Estradiol valerate [11]
MR003142 17-beta-estradiol 17-beta-estradio-3-O-sulfate metabolite Unclear Dehydroepiandrosterone [5]
MR003143 17-beta-estradiol 17-beta-estradio-3-O-sulfate-glucuronide metabolite Unclear Dehydroepiandrosterone [5]
MR003144 17-beta-estradiol Estriol Unclear Dehydroepiandrosterone [5]
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Other MR(s) Related to The Product of This MR
Other MR(s) That Produce The Product of This MR
MR ID Reactant Product MR Type Related Drug REF
MR013315 E-3A 4-hydroxyestrone Oxidation - 4-hydroxylation E-3A [11]
MR002697 Estrone 4-hydroxyestrone Oxidation - 4-Hydroxylation Estrone [12]
Other MR(s) That Metabolize The Produtc of This MR
MR ID Reactant Product MR Type Related Drug REF
MR013316 4-hydroxyestrone 4-Hydroxyestradiol Unclear E-3A [9]
MR002695 4-hydroxyestrone 4-methoxyestrone Unclear Estrone [13]
MR002643 4-hydroxyestrone 4-hydroxyestradiol Unclear Estradiol acetate [14]
MR002666 4-hydroxyestrone 4-hydroxyestradiol Unclear Estradiol cypionate [14]
MR002689 4-hydroxyestrone 4-hydroxyestradiol Unclear Estradiol valerate [14]
References
1 Pharmacokinetic and pharmacologic variation between different estrogen products J Clin Pharmacol. 1995 Sep;35(9S):18S-24S. doi: 10.1002/j.1552-4604.1995.tb04143.x.
2 Simultaneous determination of estramustine phosphate and its four metabolites in human plasma by liquid chromatography-ionspray mass spectrometry Biomed Chromatogr. 2004 Jun;18(5):293-301. doi: 10.1002/bmc.319.
3 Differential uptake of estramustine phosphate metabolites and its correlation with the levels of estramustine binding protein in prostate tumor tissue Clin Cancer Res. 1998 Sep;4(9):2079-84.
4 Metabolism of estrone sulfate by normal breast tissue: influence of menopausal status and oral contraceptives
5 Resveratrol Inhibits Key Steps of Steroid Metabolism in a Human Estrogen-Receptor Positive Breast Cancer Model: Impact on Cellular Proliferation Front Pharmacol. 2018 Jul 10;9:742. doi: 10.3389/fphar.2018.00742.
6 The metabolism of estradiol; oral compared to intravenous administration J Steroid Biochem. 1985 Dec;23(6A):1065-70. doi: 10.1016/0022-4731(85)90068-8.
7 Profiling endogenous serum estrogen and estrogen-glucuronides by liquid chromatography-tandem mass spectrometry Anal Chem. 2009 Dec 15;81(24):10143-8. doi: 10.1021/ac9019126.
8 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
9 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
10 FooDB:Estradiol acetate
11 Cytochrome P450-mediated metabolism of estrogens and its regulation in human. Cancer Lett. 2005 Sep 28;227(2):115-24.
12 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
13 Evaluation of electrospray ionization and atmospheric pressure chemical ionization for simultaneous detection of estrone and its metabolites using high-performance liquid chromatography/tandem mass spectrometry J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Dec 1;860(1):49-56. doi: 10.1016/j.jchromb.2007.10.014.
14 Cytochrome P450-mediated metabolism of estrogens and its regulation in human Cancer Lett. 2005 Sep 28;227(2):115-24. doi: 10.1016/j.canlet.2004.10.007.

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