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

General Information of Drug (ID: DR0658)
Drug Name
Ethinylestradiol propanesulfonate
Synonyms
Ethinylestradiol propanesulfonate; Ethinyl estradiol isopropylsulfonate; SCHEMBL457480; Turisteron; Turisteron (TN); XF48685MYR; ethinylestradiol sulfonate; (17; 17-Hydroxy-19-norpregna-1(10),2,4-trien-20-yn-3-yl propane-2-sulfonate; 17alpha-Ethinyl-3-isopropylsulfonyloxyestradiol; 19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol, 3-(2-propanesulfonate), (17alpha)-; 28913-23-7; A)-17-ethynyl-17-hydroxyestra-1,3,5(10)-trien-3-yl propane-2-sulfonate; AC1L2A1G; AC1Q6XYI; CHEBI:135643; D07928; DTXSID20951545; J-96; UNII-XF48685MYR
Indication Prostate cancer [ICD11: 2C82] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 402.5 Topological Polar Surface Area 72
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
68582
ChEBI ID
CHEBI:135643
CAS Number
28913-23-7
Formula
C23H30O4S
Canonical SMILES
CC(C)S(=O)(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4(C#C)O)C
InChI
1S/C23H30O4S/c1-5-23(24)13-11-21-20-8-6-16-14-17(27-28(25,26)15(2)3)7-9-18(16)19(20)10-12-22(21,23)4/h1,7,9,14-15,19-21,24H,6,8,10-13H2,2-4H3/t19-,20-,21+,22+,23+/m1/s1
InChIKey
KPEUDULLQDHKAZ-VROINQGHSA-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
Ethinylestradiol-3-sulfate DM000920
40561833
Conjugation - Sulfation 1 [2]
Ethinylestradiol-glucuronide DM006626 N. A. Conjugation - O-glucuronidation 1 [2]
Unclear DM009999 N. A. Oxidation - 16alpha-hydroxylation 1 [2] , [3]
Unclear DM009999 N. A. Oxidation - 7-hydroxylation 1 [2] , [3]
Unclear DM009999 N. A. Oxidation - 6-hydroxylation 1 [2] , [3]
Unclear DM009999 N. A. Oxidation - 4-hydroxylation 1 [2] , [3]
Unclear DM009999 N. A. Oxidation - 2-hydroxylation 1 [2] , [3]
16alpha-methoxyethinylestradiol DM000919 N. A. Conjugation - O-methylation 2 [2] , [3]
2-methoxyethinylestradiol DM000911
90470385
Conjugation - O-methylation 2 [2] , [3]
4-methoxyethinylestradiol DM000913 N. A. Conjugation - O-methylation 2 [2] , [3]
6-methoxyethinylestradiol DM000915 N. A. Conjugation - O-methylation 2 [2] , [3]
7-methoxyethinylestradiol DM000917 N. A. Conjugation - O-methylation 2 [2] , [3]
16alpha-methoxyethinylestradiol-glucuronide DM006624 N. A. Conjugation - O-glucuronidation 3 [2] , [3]
16alpha-methoxyethinylestradiol-sulfate DM006625 N. A. Conjugation - Sulfation 3 [2] , [3]
2-methoxyethinylestradiol-glucuronide DM006616 N. A. Conjugation - O-glucuronidation 3 [2] , [3]
2-methoxyethinylestradiol-sulfate DM006617 N. A. Conjugation - Sulfation 3 [2] , [3]
4-methoxyethinylestradiol-glucuronide DM006618 N. A. Conjugation - O-glucuronidation 3 [2] , [3]
4-methoxyethinylestradiol-sulfate DM006619 N. A. Conjugation - Sulfation 3 [2] , [3]
6-methoxyethinylestradiol-glucuronide DM006620 N. A. Conjugation - O-glucuronidation 3 [2] , [3]
6-methoxyethinylestradiol-sulfate DM006621 N. A. Conjugation - Sulfation 3 [2] , [3]
7-methoxyethinylestradiol-glucuronide DM006622 N. A. Conjugation - O-glucuronidation 3 [2] , [3]
7-methoxyethinylestradiol-sulfate DM006623 N. A. Conjugation - Sulfation 3 [2] , [3]
⏷ Show the Full List of 22  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007157 Ethinylestradiol propanesulfonate Ethinylestradiol-glucuronide Conjugation - O-glucuronidation UGT1A1 ... [2]
MR007158 Ethinylestradiol propanesulfonate Ethinylestradiol-3-sulfate Conjugation - Sulfation SULT1A1 ... [2]
MR014077 Ethinylestradiol propanesulfonate Unclear Oxidation - 16alpha-hydroxylation CYP3A4 ... [2], [3]
MR007142 Unclear 2-methoxyethinylestradiol Conjugation - O-methylation COMT [2], [3]
MR007145 Unclear 4-methoxyethinylestradiol Conjugation - O-methylation COMT [2], [3]
MR007148 Unclear 6-methoxyethinylestradiol Conjugation - O-methylation COMT [2], [3]
MR007151 Unclear 7-methoxyethinylestradiol Conjugation - O-methylation COMT [2], [3]
MR007154 Unclear 16alpha-methoxyethinylestradiol Conjugation - O-methylation COMT [2], [3]
MR007155 16alpha-methoxyethinylestradiol 16alpha-methoxyethinylestradiol-glucuronide Conjugation - O-glucuronidation UGT1A1 ... [2], [3]
MR007156 16alpha-methoxyethinylestradiol 16alpha-methoxyethinylestradiol-sulfate Conjugation - Sulfation SULT1A1 ... [2], [3]
MR007143 2-methoxyethinylestradiol 2-methoxyethinylestradiol-glucuronide Conjugation - O-glucuronidation UGT1A1 ... [2], [3]
MR007144 2-methoxyethinylestradiol 2-methoxyethinylestradiol-sulfate Conjugation - Sulfation SULT1A1 ... [2], [3]
MR007146 4-methoxyethinylestradiol 4-methoxyethinylestradiol-glucuronide Conjugation - O-glucuronidation UGT1A1 ... [2], [3]
MR007147 4-methoxyethinylestradiol 4-methoxyethinylestradiol-sulfate Conjugation - Sulfation SULT1A1 ... [2], [3]
MR007149 6-methoxyethinylestradiol 6-methoxyethinylestradiol-glucuronide Conjugation - O-glucuronidation UGT1A1 ... [2], [3]
MR007150 6-methoxyethinylestradiol 6-methoxyethinylestradiol-sulfate Conjugation - Sulfation SULT1A1 ... [2], [3]
MR007152 7-methoxyethinylestradiol 7-methoxyethinylestradiol-glucuronide Conjugation - O-glucuronidation UGT1A1 ... [2], [3]
MR007153 7-methoxyethinylestradiol 7-methoxyethinylestradiol-sulfate Conjugation - Sulfation SULT1A1 ... [2], [3]
⏷ Show the Full List of 18 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] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2] , [3]
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
[2] , [3]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[2] , [3]
Sulfotransferase 1E1 (SULT1E1) DME0061 Homo sapiens
ST1E1_HUMAN
2.8.2.4
[2] , [3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2] , [3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2] , [3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2] , [3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2] , [3]
⏷ Show the Full List of 11  DME(s)
References
1 Index Nominum 2000: International Drug Directory. Page: 412.
2 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.
3 Metabolism of 17 alpha-ethinylestradiol by human liver microsomes in vitro: aromatic hydroxylation and irreversible protein binding of metabolites J Clin Endocrinol Metab. 1974 Dec;39(6):1072-80. doi: 10.1210/jcem-39-6-1072.
4 The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol. Drug Metab Dispos. 2004 Nov;32(11):1209-12.

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