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

General Information of Drug (ID: DR0644)
Drug Name
Estradiol valerate
Synonyms
Estradiol valerate; Delestrogen; 979-32-8; Progynova; Neofollin; Estraval; Femogex; Progynon-Depot; Estradiol valerianate; Estradiol 17-valerate; Oestradiol valerate; Pharlon; Duratrad; Deladiol; Climaval; Atladiol; Estate; Dura-estradiol; Exten strone; Repo-Estra; Depo estro med; Estraval PA; Delestrogen 4X; Estraval 2X; Estroval-10; Delahormone unimatic; Depo-Estro-Med; Femogen-L.A.; Ronfase; Pelanin; Merimono; Cyclocur; Postoval; Nuvelle; Primogyna; Gynokadin; Estradiol Depot; Primogyn-Depot; Gynogen L.A. 20; Gynogen L.A. 40; Gynogen L.A. 10
Indication Acquired prion disease [ICD11: 8E01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 356.5 Topological Polar Surface Area 46.5
Heavy Atom Count 26 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
13791
ChEBI ID
CHEBI:31561
CAS Number
979-32-8
TTD Drug ID
D07VBA
Formula
C23H32O3
Canonical SMILES
CCCCC(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)O)C
InChI
1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1
InChIKey
RSEPBGGWRJCQGY-RBRWEJTLSA-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]
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 [10]
2-hydroxyestrone DM000871
440623
Oxidation - 2-Hydroxylation 2 [11]
2-hydroxyestrone DM000871
440623
Oxidation - Hydroxylation 2 [9] , [11]
2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) DM000880
443076
Unclear 2 [9] , [12]
2-Methoxyestrone 3-glucuronide DM000878
22833612
Unclear 2 [9]
4-hydroxyestradiol DM000873
5282360
Oxidation - Hydroxylation 2 [11]
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 [15]
2-methoxyestrone DM000872
440624
Unclear 3 [11]
4-hydroxyestradiol DM000873
5282360
Unclear 3 [15]
4-methoxyestradiol DM000874
68578
Unclear 3 [11]
Estrone DM003062
5870
Unclear 3 [10]
Estrone sulfate DM003063
3001028
Unclear 3 [14]
16-alpha hydroxyestrone DM000869
115116
Unclear 4 [10]
17-Epiestriol DM000870
256737
Unclear 5 [10]
Estriol DM003060
5756
Unclear 5 [10]
⏷ 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
MR002690 Estradiol cypionate Estradiol Hydrolysis - Esterase Hydrolysis Unclear [8]
MR002670 Estradiol 17beta-Estradiol-3,17-beta-sulfate Unclear UGT [10]
MR002671 Estradiol 2-hydroxyestrone Oxidation - Hydroxylation CYP1A2 ... [9], [11]
MR002672 Estradiol 4-hydroxyestradiol Oxidation - Hydroxylation CYP1B1 [11]
MR002673 Estradiol 4-hydroxyestrone Oxidation - 4-Hydroxylation CYP3A5 ... [9]
MR002674 Estradiol Estradiol-17beta 3-sulfate Unclear UGT [13]
MR002675 Estradiol 2-Methoxyestrone 3-glucuronide Unclear UGT1A1 [9]
MR002676 Estradiol 17-beta-Estradiol-3-glucuronide Unclear UGT1A1 [9]
MR002677 Estradiol 2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) Unclear UGT1A1 [9], [12]
MR002678 Estradiol 17-beta-Estradiol glucuronide Unclear Unclear [9]
MR002679 Estradiol 17alpha-Estradiol-3-glucuronide Unclear UGT1A1 [9]
MR002680 Estradiol Estradiol-17alpha 3-D-glucuronoside Unclear UGT1A1 [9]
MR002681 Estradiol 17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide) Unclear UGT1A1 [9]
MR002682 Estradiol Estrone Unclear HSD17B1 [14]
MR002683 17beta-Estradiol-3,17-beta-sulfate Estrone Unclear CYP1A2 [10]
MR002686 2-hydroxyestrone 2-methoxyestrone Unclear Unclear [11]
MR002687 2-hydroxyestrone 2-hydroxyestradiol Unclear COMT [15]
MR002688 4-hydroxyestradiol 4-methoxyestradiol Unclear COMT [11]
MR002689 4-hydroxyestrone 4-hydroxyestradiol Unclear Unclear [15]
MR002692 Estrone Estrone sulfate Unclear STS ... [14]
MR002691 Estrone 16alpha hydroxyestrone Unclear Unclear [10]
MR002684 16alpha hydroxyestrone 17-Epiestriol Unclear Unclear [10]
MR002685 16alpha hydroxyestrone Estriol Unclear Unclear [10]
⏷ 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
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Steryl-sulfatase (STS) DMEN025 Homo sapiens
STS_HUMAN
1.14.13.39
[6]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[7]
⏷ Show the Full List of 9  DME(s)
References
1 Estradiol Valerate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals. Drug Metab Dispos. 2006 Sep;34(9):1606-14.
3 Role of cytochrome P450 in estradiol metabolism in vitro. Acta Pharmacol Sin. 2001 Feb;22(2):148-54.
4 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
5 Drug Interactions Flockhart Table
6 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes Life Sci. 2010 Aug 14;87(7-8):261-8. doi: 10.1016/j.lfs.2010.07.001.
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 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
11 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
12 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.
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.
15 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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