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

General Information of Drug (ID: DR0636)
Drug Name
Estradiol acetate
Synonyms
Estradiol 3-acetate; Estradiol acetate (USAN); Estradiol acetate [USAN]; Estradiol, 3-acetate; Estradiol-3-acetate; FHXBMXJMKMWVRG-SLHNCBLASA-N; Femring; Femring (TN); Menoring; UNII-5R97F5H93P; beta-Estradiol 3-acetate; 17beta-Estradiol 3-acetate; 17beta-Hydroxy-3-acetoxyestra-1,3,5(10)-triene; 3-Acetoxyestra-1,3,5(10)-trien-17beta-ol; 3-O-Acetylestradiol; 4245-41-4; 5R97F5H93P; CAS-4245-41-4; DSSTox_CID_25867; DSSTox_GSID_45867; DSSTox_RID_81186; E 3A; E3A; Estra-1,3,5(10)-triene-3,17beta-diyl 3-acetate
Indication Acquired prion disease [ICD11: 8E01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 314.4 Topological Polar Surface Area 46.5
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
9818306
ChEBI ID
CHEBI:135981
CAS Number
4245-41-4
TTD Drug ID
D0T7ZQ
Formula
C20H26O3
Canonical SMILES
CC(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4O)C
InChI
1S/C20H26O3/c1-12(21)23-14-4-6-15-13(11-14)3-5-17-16(15)9-10-20(2)18(17)7-8-19(20)22/h4,6,11,16-19,22H,3,5,7-10H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1
InChIKey
FHXBMXJMKMWVRG-SLHNCBLASA-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
Estradiol-17 beta DM000867
5757
Hydrolysis - Esterase Hydrolysis 1 [8]
17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide) DM000884
5281895
Unclear 2 [9]
17-beta-Estradiol glucuronide DM000881
66424
Unclear 2 [9] , [10]
17-beta-Estradiol-3-glucuronide DM000879
13783824
Unclear 2 [9]
17alpha-Estradiol-3-glucuronide DM000882
66651
Unclear 2 [9]
17beta-Estradiol-3,17-beta-sulfate DM000868
66430
Unclear 2 [11]
2-hydroxyestrone DM000871
440623
Oxidation - Hydroxylation 2 [12]
2-hydroxyestrone DM000871
440623
Oxidation - 2-Hydroxylation 2 [9] , [12]
2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) metabolite DM002029 N. A. Unclear 2 [9]
2-Methoxyestrone 3-glucuronide DM000878
22833612
Unclear 2 [9]
4-hydroxyestradiol DM000873
5282360
Unclear 2 [12]
4-hydroxyestrone DM000876
53477797
Oxidation - 4-Hydroxylation 2 [9]
Estradiol-17alpha 3-D-glucuronoside DM000883
11988264
Unclear 2 [9]
Estradiol-17beta 3-sulfate DM000877
53477783
Unclear 2 [13]
Estrone DM003062
5870
Unclear 2 [14]
2-hydroxyestradiol DM000875
247304
Unclear 3 [2]
2-methoxyestrone DM000872
440624
Unclear 3 [12]
4-hydroxyestradiol DM000873
5282360
Unclear 3 [2]
4-methoxyestradiol DM000874
68578
Unclear 3 [12]
Estrone DM003062
5870
Unclear 3 [11]
Estrone sulfate DM003063
3001028
Unclear 3 [14]
16-alpha hydroxyestrone DM000869
115116
Unclear 4 [11]
17-Epiestriol DM000870
256737
Unclear 5 [11]
Estriol DM003060
5756
Unclear 5 [11]
⏷ Show the Full List of 24  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002644 Estradiol acetate Estradiol Hydrolysis - Esterase Hydrolysis Unclear [8]
MR002624 Estradiol 17beta-Estradiol-3,17-beta-sulfate Unclear Unclear [11]
MR002625 Estradiol 2-hydroxyestrone Oxidation - 2-Hydroxylation CYP3A4 ... [9], [12]
MR002626 Estradiol 4-hydroxyestradiol Unclear CYP1B1 [12]
MR002627 Estradiol 4-hydroxyestrone Oxidation - 4-Hydroxylation CYP3A5 ... [9]
MR002628 Estradiol Estradiol-17beta 3-sulfate Unclear UGT [13]
MR002629 Estradiol 2-Methoxyestrone 3-glucuronide Unclear UGT [9]
MR002630 Estradiol 17-beta-Estradiol-3-glucuronide Unclear Unclear [9]
MR002631 Estradiol 17-beta-Estradiol glucuronide Unclear Unclear [9], [10]
MR002632 Estradiol 17alpha-Estradiol-3-glucuronide Unclear UGT [9]
MR002633 Estradiol Estradiol-17alpha 3-D-glucuronoside Unclear UGT [9]
MR002634 Estradiol 17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide) Unclear UGT [9]
MR002635 Estradiol 2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) metabolite Unclear Unclear [9]
MR002636 Estradiol Estrone Unclear HSD17B1 [14]
MR002637 17beta-Estradiol-3,17-beta-sulfate Estrone Unclear Unclear [11]
MR002640 2-hydroxyestrone 2-methoxyestrone Unclear Unclear [12]
MR002641 2-hydroxyestrone 2-hydroxyestradiol Unclear COMT [2]
MR002642 4-hydroxyestradiol 4-methoxyestradiol Unclear COMT [12]
MR002643 4-hydroxyestrone 4-hydroxyestradiol Unclear Unclear [2]
MR002646 Estrone Estrone sulfate Unclear STS ... [14]
MR002645 Estrone 16alpha hydroxyestrone Unclear Unclear [11]
MR002638 16alpha hydroxyestrone 17-Epiestriol Unclear Unclear [11]
MR002639 16alpha hydroxyestrone Estriol Unclear Unclear [11]
⏷ Show the Full List of 23 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
Steryl-sulfatase (STS) DMEN025 Homo sapiens
STS_HUMAN
1.14.13.39
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[7]
⏷ Show the Full List of 12  DME(s)
References
1 Estradiol Valerate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 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.
4 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
5 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
6 Role of cytochrome P450 in estradiol metabolism in vitro. Acta Pharmacol Sin. 2001 Feb;22(2):148-54.
7 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
8 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.
9 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.
10 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.
11 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
12 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
13 FooDB:Estradiol acetate
14 Cytochrome P450-mediated metabolism of estrogens and its regulation in human. Cancer Lett. 2005 Sep 28;227(2):115-24.

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