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

General Information of Drug (ID: DR0431)
Drug Name
Dehydroepiandrosterone
Synonyms
Dehydroepiandrosterone; Dehydroisoandrosterone; Diandron; Diandrone; Epiandrosterone, 5-dehydro-; Intrarosa; PRASTERONE; Andrestenol; Androstenolone; Dehydro-epi-androsterone; Prasterona; Prasteronum; Prestara; Psicosterone; Siscelar plus; dehydroepiandrosterone (dhea); trans-Dehydroandrosterone; 17-Chetovis; 17-Hormoforin; 3-beta-Hydroxy-5-androsten-17-one; 3beta-hydroxyandrost-5-en-17-one; 5,6-Dehydroisoandrosterone; 5,6-Dehydroisoandrostorone; 5,6-Didehydroisoandrosterone; 5-Dehydroepiandrosterone; 53-43-0; Caswell No. 051F; DHEA
Indication Dyspareunia [ICD11: GA12] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 288.4 Topological Polar Surface Area 37.3
Heavy Atom Count 21 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5881
PubChem SID
1983 ; 4449 ; 75250 ; 596018 ; 837865 ; 841442 ; 3135651 ; 7885884 ; 8145544 ; 8153636 ; 11446567 ; 12014907 ; 12146065 ; 14751238 ; 14775640 ; 17404931 ; 24278369 ; 24702275 ; 26703947 ; 29224908 ; 46387028 ; 46508824 ; 47193749 ; 47959958 ; 48413520 ; 48415849 ; 49681751 ; 49747225 ; 49857278 ; 50172721 ; 53777474 ; 53788218 ; 56312069 ; 56312916 ; 56313484 ; 56313819 ; 56320669 ; 56320670 ; 57323014 ; 87566797 ; 91692812 ; 92297484 ; 92303742 ; 92308678 ; 92309040 ; 92709895 ; 93167098 ; 96025095 ; 103302695 ; 104095449
ChEBI ID
ChEBI:28689
CAS Number
53-43-0
TTD Drug ID
D0K0EK
Formula
C19H28O2
Canonical SMILES
CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(C4)O)C
InChI
1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
InChIKey
FMGSKLZLMKYGDP-USOAJAOKSA-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
Androst-4-ene-3,17-dione (4ADN) DM001962
6128
Unclear 1 [12]
Dehydroepiandrosterone sulfate metabolite DM001968
12594
Unclear 1 [12]
Estradiol-17 beta DM000867
5757
Unclear 2 [12]
Estrone DM003062
5870
Unclear 2 [12]
Testosterone DM001963
6013
Unclear 2 [12]
17-beta-estradio-3-O-sulfate metabolite DM001965
66416
Unclear 3 [12]
17-beta-estradio-3-O-sulfate-glucuronide metabolite DM001966 N. A. Unclear 3 [12]
Estradiol-17 beta DM000867
5757
Unclear 3 [12]
Estriol DM003060
5756
Unclear 3 [12]
Estrone sulfate DM003063
3001028
Unclear 3 [13]
17-beta-estradio-3-O-sulfate metabolite DM001965
66416
Unclear 4 [12]
17-beta-estradio-3-O-sulfate-glucuronide metabolite DM001966 N. A. Unclear 4 [12]
Estriol DM003060
5756
Unclear 4 [12]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003149 Dehydroepiandrosterone 4-androstene-3,17-dione(AD) Unclear HSD3B1 [12]
MR003150 Dehydroepiandrosterone Dehydroepiandrosterone sulfate metabolite Unclear SULT2A1 [12]
MR003145 4-androstene-3,17-dione(AD) Estradiol-17 beta Unclear Unclear [12]
MR003146 4-androstene-3,17-dione(AD) Testosterone Unclear HSD17B1 [12]
MR003147 4-androstene-3,17-dione(AD) Estrone Unclear CYP3A4 [12]
MR003151 Estrone Estrone sulfate Unclear CYP19A1 [13]
MR003148 Testosterone Estradiol-17 beta Unclear CYP19A1 [12]
MR003142 17-beta-estradiol 17-beta-estradio-3-O-sulfate metabolite Unclear SULT [12]
MR003143 17-beta-estradiol 17-beta-estradio-3-O-sulfate-glucuronide metabolite Unclear UGT [12]
MR003144 17-beta-estradiol Estriol Unclear CYP3A4 [12]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aromatase (CYP19A1) DME0002 Homo sapiens
CP19A_HUMAN
1.14.14.14
[2]
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Homo sapiens
3BHS2_HUMAN
1.1.1.145
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Cytochrome P450 7B1 (CYP7B1) DME0608 Homo sapiens
CP7B1_HUMAN
1.14.14.29
[6]
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Homo sapiens
3BHS1_HUMAN
1.1.1.145
[3]
Estradiol 17-beta-dehydrogenase 1 (HSD17B1) DME0420 Homo sapiens
DHB1_HUMAN
1.1.1.62
[7]
Estradiol 17-beta-dehydrogenase 2 (HSD17B2) DME0422 Homo sapiens
DHB2_HUMAN
1.1.1.62
[7]
Peroxisomal multifunctional enzyme 2 (HSD17B4) DME0263 Homo sapiens
DHB4_HUMAN
4.2.1.119
[7]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[8]
Sulfotransferase 2B1 (SULT2B1) DME0384 Homo sapiens
ST2B1_HUMAN
2.8.2.2
[9]
⏷ Show the Full List of 11  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Km = 0.00164 microM
3BHS1_HUMAN
[10]
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Km = 0.00164 microM
3BHS2_HUMAN
[11]
Sulfotransferase 2A1 (SULT2A1) DME0074 Km = 0.002 microM
ST2A1_HUMAN
[8]
References
1 Dehydroepiandrosterone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Urinary and serum octopamine in patients with portal-systemic encephalopathy. Lancet. 1975 Nov 15;2(7942):943-6.
3 Selective inhibition of human 3beta-hydroxysteroid dehydrogenase type 1 as a potential treatment for breast cancer. J Steroid Biochem Mol Biol. 2011 May;125(1-2):57-65.
4 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
5 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
6 CYP7B1-mediated metabolism of dehydroepiandrosterone and 5alpha-androstane-3beta,17beta-diol--potential role(s) for estrogen signaling. FEBS J. 2008 Apr;275(8):1778-89.
7 Steroid signalling in the ovarian surface epithelium. Trends Endocrinol Metab. 2005 Sep;16(7):327-33.
8 Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
9 Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b). J Steroid Biochem Mol Biol. 2001 Jun;77(4-5):261-9.
10 Structure/function relationships responsible for the kinetic differences between human type 1 and type 2 3beta-hydroxysteroid dehydrogenase and for the catalysis of the type 1 activity. J Biol Chem. 2002 Nov 8;277(45):42795-801.
11 Identification of key amino acids responsible for the substantially higher affinities of human type 1 3beta-hydroxysteroid dehydrogenase/isomerase (3beta-HSD1) for substrates, coenzymes, and inhibitors relative to human 3beta-HSD2. J Biol Chem. 2005 Jun 3;280(22):21321-8.
12 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.
13 Dehydroepiandrosterone Research: Past, Current, and Future Vitam Horm. 2018;108:1-28. doi: 10.1016/bs.vh.2018.02.002.

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