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

General Information of Drug (ID: DR0656)
Drug Name
Ethinyl estradiol
Synonyms
Ertonyl; Esteed; Estigyn; Estinyl; Eston-E; Estoral; Estorals; Ethidol; Ethinoral; Ethinyloestradiol; Ethynyl estradiol; Ethynylestradiol; Eticyclin; Eticyclol; Etinestrol; Etinestryl; Etinoestryl; Etistradiol; Feminone; Follicoral; Amenoron; Diogyn E; Dyloform; ETHINYLESTRADIOL; Ginestrene; Inestra; Linoral; Lynoral; Menolyn; Neo-Estrone; Nogest-S; Novestrol; Oradiol; Orestralyn; Palonyl; Perovex; Primogyn; Primogyn C; Primogyn M; Progynon C; Spanestrin; ethinyl estradiol; 17-Ethinylestradiol; 17-Ethynylestradiol; 17alpha-Ethynylestradiol; 57-63-6
Indication Menopausal disorder [ICD11: GA30] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 296.4 Topological Polar Surface Area 40.5
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5991
PubChem SID
9737 ; 76025 ; 7847620 ; 7979198 ; 8139942 ; 8153725 ; 11404629 ; 11533305 ; 14898199 ; 14922735 ; 17389896 ; 24702258 ; 24714981 ; 24869989 ; 24894585 ; 26512288 ; 26719638 ; 26753042 ; 29215113 ; 29225006 ; 46386858 ; 46508618 ; 48413731 ; 48415973 ; 48421874 ; 48423390 ; 48425117 ; 49854450 ; 53788253 ; 56311124 ; 56311183 ; 56311332 ; 56311399 ; 56311403 ; 56311406 ; 56311535 ; 56312680 ; 56313453 ; 56313621 ; 56313838 ; 56313881 ; 56314241 ; 57288591 ; 57650750 ; 71821446 ; 78032044 ; 81093168 ; 92308409 ; 92713395 ; 93165614
ChEBI ID
ChEBI:4903
CAS Number
57-63-6
TTD Drug ID
D06NXY
Formula
C20H24O2
Canonical SMILES
CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
InChI
1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
InChIKey
BFPYWIDHMRZLRN-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
16alpha-hydroxyethinylestradiol DM000918
11723045
Oxidation - 16-Hydroxylation 1 [2]
2-hydroxyethinylestradiol DM000910
71777553
Oxidation - 2-Hydroxylation 1 [2]
4-hydroxyethinylestradiol DM000912
21114722
Oxidation - 4-Hydroxylation 1 [2]
6-hydroxyethinylestradiol DM000914
21121304
Oxidation - 6-Hydroxylation 1 [2]
7-hydroxyethinylestradiol DM000916 N. A. Oxidation - 7-Hydroxylation 1 [2]
Ethinylestradiol-17-sulfate DM000922
67091
Conjugation - Sulfation 1 [10]
Ethinylestradiol-3,17-sulfate DM000921 N. A. Conjugation - Sulfation 1 [10]
Ethinylestradiol-3-sulfate DM000920
40561833
Conjugation - Sulfation 1 [2]
N-desmethylzopiclone DM000907
162892
Conjugation - O-Glucuronidation 1 [9]
16alpha-methoxyethinylestradiol DM000919 N. A. Conjugation - O-Methylation 2 [3]
2-methoxyethinylestradiol DM000911
90470385
Conjugation - O-Methylation 2 [3]
4-methoxyethinylestradiol DM000913 N. A. Conjugation - O-Methylation 2 [3]
6-methoxyethinylestradiol DM000915 N. A. Conjugation - O-Methylation 2 [3]
7-methoxyethinylestradiol DM000917 N. A. Conjugation - O-Methylation 2 [3]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002720 Ethinyl estradiol N-desmethylzopiclone Conjugation - O-Glucuronidation UGT1A1 ... [9]
MR002721 Ethinyl estradiol 2-hydroxyethinylestradiol Oxidation - 2-Hydroxylation CYP3A4 ... [2]
MR002722 Ethinyl estradiol 4-hydroxyethinylestradiol Oxidation - 4-Hydroxylation CYP3A4 ... [2]
MR002723 Ethinyl estradiol 6-hydroxyethinylestradiol Oxidation - 6-Hydroxylation CYP3A4 ... [2]
MR002724 Ethinyl estradiol 7-hydroxyethinylestradiol Oxidation - 7-Hydroxylation CYP3A4 ... [2]
MR002725 Ethinyl estradiol 16alpha-hydroxyethinylestradiol Oxidation - 16-Hydroxylation CYP3A4 ... [2]
MR002726 Ethinyl estradiol Ethinylestradiol-3-sulfate Conjugation - Sulfation CES1 ... [2]
MR002727 Ethinyl estradiol Ethinylestradiol-3,17-sulfate Conjugation - Sulfation CES1 ... [10]
MR002728 Ethinyl estradiol Ethinylestradiol-17-sulfate Conjugation - Sulfation CES1 ... [10]
MR002719 16alpha-hydroxyethinylestradiol 16alpha-methoxyethinylestradiol Conjugation - O-Methylation COMT [3]
MR002715 2-hydroxyethinylestradiol 2-methoxyethinylestradiol Conjugation - O-Methylation COMT [3]
MR002716 4-hydroxyethinylestradiol 4-methoxyethinylestradiol Conjugation - O-Methylation COMT [3]
MR002717 6-hydroxyethinylestradiol 6-methoxyethinylestradiol Conjugation - O-Methylation COMT [3]
MR002718 7-hydroxyethinylestradiol 7-methoxyethinylestradiol Conjugation - O-Methylation COMT [3]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[3]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5]
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
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[7]
Sulfotransferase 1A3 (SULT1A3) DME0063 Homo sapiens
ST1A3_HUMAN
2.8.2.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[8]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[9]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[9]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[9]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[9]
⏷ Show the Full List of 14  DME(s)
References
1 Ethinyl Estradiol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Sulfotransferase 1E1 is a low km isoform mediating the 3-O-sulfation of ethinyl estradiol Drug Metab Dispos. 2004 Nov;32(11):1299-303. doi: 10.1124/dmd.32.11..
3 Genetic variation in the first-pass metabolism of ethinylestradiol, sex hormone binding globulin levels and venous thrombosis risk Eur J Intern Med. 2017 Jul;42:54-60. doi: 10.1016/j.ejim.2017.05.019.
4 The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol. Drug Metab Dispos. 2004 Nov;32(11):1209-12.
5 Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78.
6 Rifampicin, a keystone inducer of drug metabolism: from Herbert Remmer's pioneering ideas to modern concepts. Drug Metab Rev. 2004 Oct;36(3-4):497-509.
7 The effect of ethinyloestradiol and levonorgestrel on the CYP2C19-mediated metabolism of omeprazole in healthy female subjects. Br J Clin Pharmacol. 2003 Aug;56(2):232-7.
8 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
9 Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol Mol Pharmacol. 1993 Apr;43(4):649-54.
10 The pharmacokinetics and metabolism of ethinyl estradiol and its three sulfates in the baboon Am J Obstet Gynecol. 1983 May 1;146(1):80-7. doi: 10.1016/0002-9378(83)90931-6.

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