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

General Information of Drug (ID: DR0492)
Drug Name
Diethylstilbestrol
Synonyms
Diastyl; Diethylstilbesterol; Distilbene; Domestrol; Dyestrol; Estrobene; Estromenin; Estrosyn; Fonatol; Grafestrol; Iscovesco; Makarol; Menostilbeen; Micrest; Microest; Milestrol; OeKolp; Oestrogenine; Oestromenin; Oestromensyl; Oestromienin; Pabestrol; Palestrol; Serral; Sexocretin; Stilbestrol; Stilbestrone; Stilbetin; Stilboefral; Agostilben; Antigestil; Comestrol; Cyren A; Stilboestroform; Stilboestrol; Stilbofolin; Stilkap; Synestrin; Synthoestrin; Synthofolin; Syntofolin; Vagestrol; diethylstilbestrol; 56-53-1; Bufon; Cyren; Desma; Sibol
Indication Vaginitis [ICD11: GA02] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 268.3 Topological Polar Surface Area 40.5
Heavy Atom Count 20 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
448537
PubChem SID
9822 ; 69617 ; 584119 ; 584187 ; 832397 ; 835330 ; 866308 ; 3138565 ; 3719650 ; 7847643 ; 7886973 ; 7979077 ; 8149301 ; 10300220 ; 10321979 ; 10527511 ; 11532921 ; 14848307 ; 17389919 ; 24853100 ; 24869934 ; 24893887 ; 26611702 ; 26679895 ; 26697273 ; 26747240 ; 26747241 ; 26752777 ; 36890357 ; 47213212 ; 47291097 ; 47515286 ; 47588959 ; 47662244 ; 47885370 ; 47959699 ; 48334454 ; 48413611 ; 48415890 ; 48421868 ; 48423301 ; 48425067 ; 49688699 ; 49698632 ; 49854439 ; 50047747 ; 50105424 ; 50105425 ; 50612427 ; 53788568
ChEBI ID
ChEBI:41922
CAS Number
56-53-1
TTD Drug ID
D0Y2NE
Formula
C18H20O2
Canonical SMILES
CCC(=C(CC)C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
InChI
1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+
InChIKey
RGLYKWWBQGJZGM-ISLYRVAYSA-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
1-hydroxy-Z,Z-dienestrol DM000071 N. A. Oxidation - Oxidation 1 [4]
3'-hydroxy-diethylstilbestro DM000072 N. A. Reduction - Reduction 1 [4]
Alpha-OH DES DM000068 N. A. Oxidation - Oxidation 1 [5]
DES SQ DM000066 N. A. Oxidation - Oxidation 1 [5]
E-DES-3,Coxide DM000073 N. A. Reduction - Reduction 1 [6]
Z,Z-dienestrol DM000070
5356512
Oxidation - Oxidation 1 [6] , [4]
Alpha-OSO3 DES DM000069 N. A. Conjugation - Conjugation 2 [5]
Diethylstilbestrol quinone DM000067
3034826
Oxidation - Oxidation 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000831 Diethylstilbestrol DES SQ Oxidation - Oxidation CYP [5]
MR000832 Diethylstilbestrol Alpha-OH DES Oxidation - Oxidation CYP [5]
MR000833 Diethylstilbestrol Z,Z-dienestrol Oxidation - Oxidation Unclear [6], [4]
MR000834 Diethylstilbestrol 1-hydroxy-Z,Z-dienestrol Oxidation - Oxidation Unclear [4]
MR000835 Diethylstilbestrol 3'-hydroxy-diethylstilbestro Reduction - Reduction Unclear [4]
MR000836 Diethylstilbestrol E-DES-3,Coxide Reduction - Reduction Unclear [6]
MR000830 Alpha-OH DES Alpha-OSO3 DES Conjugation - Conjugation SULT [5]
MR000829 DES SQ Diethylstilbestrol quinone Oxidation - Oxidation CYP [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Diethylstilbestrol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21.
3 Comparative analysis of human CYP3A4 and rat CYP3A1 induction and relevant gene expression by bisphenol A and diethylstilbestrol: implications for toxicity testing paradigms. Reprod Toxicol. 2013 Jun;37:24-30.
4 Metabolic activation of diethylstilbestrol and 7,8-benzoflavone in hamster hepatocytes Arch Toxicol Suppl. 1989;13:203-5. doi: 10.1007/978-3-642-74117-3_30.
5 Crude Edible Fig (Ficus carica) Leaf Extract Prevents Diethylstilbestrol (DES)-Induced DNA Strand Breaks in Single-Cell Gel Electrophoresis (SCGE)/Comet Assay: Literature Review and Pilot Study J Bioequivalence Bioavailab. 2019;11(2):19-28. doi: 10.35248/0975-0851.19.11.389.
6 The metabolism of diethylstilbestrol CRC Crit Rev Biochem. 1981;10(3):171-212. doi: 10.3109/10409238109113599.

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