Details of the Drug

General Information of Drug (ID: DMN3UXQ)

Drug Name
Diethylstilbestrol
Synonyms
Acnestrol; Agostilben; Antigestil; Apstil; Bufon; Climaterine; Comestrol; Cyren; DES; Desma; Destrol; Diaethylstilboestrolum; Diastyl; Dibestrol; Dicorvin; Diethylstilbesterol; Diethylstilbestrolum; Diethylstilboesterol; Dietilestilbestrol; Dietilstilbestrolo; Distilbene; Domestrol; Dyestrol; Estril; Estrobene; Estrogenine; Estromenin; Estrosyn; Fonatol; Grafestrol; Gynopharm; Hibestrol; Idroestril; Iscovesco; Makarol; Menostilbeen; Micrest; Microest; Milestrol; OeKolp; Oestrogenine; Oestrolmensil; Oestromenin; Oestromensil; Oestromensyl; Oestromienin; Oestromon; Pabestrol; Palestrol; Protectona; Sedestran; Serral; Sexocretin; Sibol; Sintestrol; Stibilium; Stilbestroform; Stilbestrol; Stilbestrone; Stilbetin; Stilboefral; Stilboestroform; Stilboestrol; Stilbofolin; Stilbofollin; Stilbol; Stilkap; Strobene; Synestrin; Synthestrin; Synthoestrin; Synthofolin; Syntofolin; Tampovagan; Tylosterone; Vagestrol; APS Brand of Diethylstilbestrol; Anti gestil; Co Pharma Brand of Diethylstilbestrol; Comestrol estrobene; Cyren A; Diethylstilbestrol BP; Dietilestilbestrol [Spanish]; Dietilstilbestrolo [DCIT]; Estilbin MCO; Gerda Brand of Diethylstilbestrol; Oestrol vetag; Percutatrine oestrogenique iscovesco; ST IL; Stilbene Estrogen; Tampovagan stilboestrol; DiBestrol 2 Premix; MG 137; Rumestrol 1; Rumestrol 2; Cis-Des; Cis-Diethylstilbesterol; Cis-Diethylstilbestrol; Co-Pharma Brand of Diethylstilbestrol; DES (synthetic estrogen); Dawe's destrol; Di-Estryl; Diethylstilbestrol (DES); Diethylstilbestrol [USAN:INN]; Diethylstilbestrol, Disodium Salt; Diethylstilbestrolum [INN-Latin]; Dietilestilbestrol [INN-Spanish]; E-Diethylstilbestrol; Estilbin (MCO); Estrogen, Stilbene; Hi-Bestrol; Neo-Oestranol 1; Neo-Oestranol I; Neo-oe stranol 1; New-Estranol 1; Stil-Rol; Stilbestrol (TN); TRANS-DIETHYSTILBESTEROL; TRANSGENIC MODEL EVALUATION (DES); Trans-Diethylstilbesterol; Trans-Diethylstilbestrol; Trans-Diethylstilboesterol; DiBestrol "2" Premix; Dibestrol '2' premix; Diethylstilbestrol (USP/INN); Alpha,alpha'-Diethylstilbenediol; Diethylstilbestrol, (Z)-Isomer; Alpha,alpha'-Diethyl-4,4'-stilbenediol; (E)-3,4-Bis(4-hydroxyphenyl)-3-hexene; (E)-4,4'-(hex-3-ene-3,4-diyl)diphenol; (E)-Diethylstilbestrol; 3,4'(4,4'-Dihydroxyphenyl)hex-3-ene; 3,4-Bis(p-hydroxyphenyl)-3-hexene; 3,4-bis(4-hydroxyphenyl)hex-3-ene; 4,4'-(3E)-hex-3-ene-3,4-diyldiphenol; 4,4'-Dihydroxydiethylstilbene; 4,4'-hex-3-ene-3,4-diyldiphenol
Indication
Disease Entry ICD 11 Status REF
Gonorrheal vaginitis GA02 Approved [1]
Therapeutic Class
Anticancer Agents
Affected Organisms
Humans and other mammals
ATC Code
G03CB02: Diethylstilbestrol
G03CB: Synthetic estrogens, plain
G03C: ESTROGENS
G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G: GENITO URINARY SYSTEM AND SEX HORMONES
G03CB02: Diethylstilbestrol
G03CB: Synthetic estrogens, plain
G03C: ESTROGENS
G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G: GENITO URINARY SYSTEM AND SEX HORMONES
G03CC05: Diethylstilbestrol
G03CC: Estrogens, combinations with other drugs
G03C: ESTROGENS
G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G: GENITO URINARY SYSTEM AND SEX HORMONES
L02AA01: Diethylstilbestrol
L02AA: Estrogens
L02A: HORMONES AND RELATED AGENTS
L02: ENDOCRINE THERAPY
L: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 268.3
Logarithm of the Partition Coefficient (xlogp) 5.1
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C18H20O2
IUPAC Name
4-[(E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
Canonical SMILES
CC/C(=C(/CC)\\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)O
InChI
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
Cross-matching ID
PubChem CID
448537
ChEBI ID
CHEMBL411
CAS Number
56-53-1
UNII
731DCA35BT
DrugBank ID
DB00255
TTD ID
D0Y2NE
VARIDT ID
DR00922
INTEDE ID
DR0492
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Agonist [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-acyl-sn-glycerol-3-phosphate acyltransferase beta (AGPAT2) OT5I4Y9K PLCB_HUMAN Gene/Protein Processing [6]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1 (PLCB1) OT9HYT7A PLCB1_HUMAN Gene/Protein Processing [7]
14-3-3 protein beta/alpha OTGBS3RF 1433B_HUMAN Gene/Protein Processing [8]
17-beta-hydroxysteroid dehydrogenase type 1 (HSD17B1) OT6EBDHM DHB1_HUMAN Gene/Protein Processing [9]
26S proteasome non-ATPase regulatory subunit 1 (PSMD1) OTW258OV PSMD1_HUMAN Gene/Protein Processing [6]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1) OTNAZVKB 3BHS1_HUMAN Gene/Protein Processing [9]
3-hydroxyisobutyrate dehydrogenase, mitochondrial (HIBADH) OTCMMMIZ 3HIDH_HUMAN Gene/Protein Processing [6]
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT5 (FUT5) OTOPGL9M FUT5_HUMAN Gene/Protein Processing [7]
5-hydroxymethyl-dUMP N-hydrolase (DNPH1) OTEZVTI1 DNPH1_HUMAN Gene/Protein Processing [8]
A disintegrin and metalloproteinase with thrombospondin motifs 9 (ADAMTS9) OTV3Q0DS ATS9_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Gonorrheal vaginitis
ICD Disease Classification GA02
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
P-glycoprotein 1 (ABCB1) DTP P-GP 7.23E-01 -8.20E-02 -3.22E-01
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 9.78E-01 -3.38E-03 -5.71E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 9.85E-01 2.24E-02 7.33E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Diethylstilbestrol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Voriconazole DMAOL2S Moderate Decreased metabolism of Diethylstilbestrol caused by Voriconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [10]
Posaconazole DMUL5EW Moderate Decreased metabolism of Diethylstilbestrol caused by Posaconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [10]
Clarithromycin DM4M1SG Moderate Decreased metabolism of Diethylstilbestrol caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [11]
Telithromycin DMZ4P3A Moderate Decreased metabolism of Diethylstilbestrol caused by Telithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [12]
Lapatinib DM3BH1Y Moderate Decreased metabolism of Diethylstilbestrol caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [13]
Aprepitant DM053KT Moderate Decreased metabolism of Diethylstilbestrol caused by Aprepitant mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [14]
Nefazodone DM4ZS8M Moderate Decreased metabolism of Diethylstilbestrol caused by Nefazodone mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [15]
Rufinamide DMWE60C Moderate Increased metabolism of Diethylstilbestrol caused by Rufinamide mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [16]
Dantrolene DM1D8XY Major Increased risk of hepatotoxicity by the combination of Diethylstilbestrol and Dantrolene. Fever [MG26] [17]
Itraconazole DMCR1MV Moderate Decreased metabolism of Diethylstilbestrol caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [10]
Clotrimazole DMMFCIH Moderate Decreased metabolism of Diethylstilbestrol caused by Clotrimazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [10]
Miconazole DMPMYE8 Moderate Decreased metabolism of Diethylstilbestrol caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [10]
Ketoconazole DMPZI3Q Moderate Decreased metabolism of Diethylstilbestrol caused by Ketoconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [10]
Cimetidine DMH61ZB Minor Decreased metabolism of Diethylstilbestrol caused by Cimetidine. Gastro-oesophageal reflux disease [DA22] [18]
ABT-450 DMFW860 Major Decreased metabolism of Diethylstilbestrol caused by ABT-450 mediated inhibition of UGT. Hepatitis virus infection [1E50-1E51] [19]
Conivaptan DM1V329 Moderate Decreased metabolism of Diethylstilbestrol caused by Conivaptan mediated inhibition of CYP450 enzyme. Hypo-osmolality/hyponatraemia [5C72] [20]
Liothyronine DM6IR3P Moderate Decreased plasma concentration of Diethylstilbestrol caused by Liothyronine mediated increased concentration of serum thyroid-binding globulin. Hypo-thyroidism [5A00] [21]
Levothyroxine DMHN027 Moderate Decreased plasma concentration of Diethylstilbestrol caused by Levothyroxine mediated increased concentration of serum thyroid-binding globulin. Hypo-thyroidism [5A00] [21]
Melatonin DMKWFBT Minor Decreased metabolism of Diethylstilbestrol caused by Melatonin mediated inhibition of CYP450 enzyme. Insomnia [7A00-7A0Z] [11]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Diethylstilbestrol caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [16]
Carfilzomib DM48K0X Major Additive thrombogenic effects by the combination of Diethylstilbestrol and Carfilzomib. Multiple myeloma [2A83] [11]
Modafinil DMYILBE Minor Increased metabolism of Diethylstilbestrol caused by Modafinil mediated induction of CYP450 enzyme. Narcolepsy [7A20] [22]
Armodafinil DMGB035 Minor Increased metabolism of Diethylstilbestrol caused by Armodafinil mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [22]
Warfarin DMJYCVW Moderate Antagonize the effect of Diethylstilbestrol when combined with Warfarin. Supraventricular tachyarrhythmia [BC81] [23]
⏷ Show the Full List of 24 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2801).
2 Effects of diethylstilbestrol on programmed oocyte death and induction of polyovular follicles in neonatal mouse ovaries. Biol Reprod. 2009 Nov;81(5):1002-9.
3 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
4 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.
5 Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21.
6 Identification of biomarkers and outcomes of endocrine disruption in human ovarian cortex using In Vitro Models. Toxicology. 2023 Feb;485:153425. doi: 10.1016/j.tox.2023.153425. Epub 2023 Jan 5.
7 Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. Toxicol Appl Pharmacol. 2009 Apr 1;236(1):85-96.
8 Analysis of gene expression induced by diethylstilbestrol (DES) in human primitive Mullerian duct cells using microarray. Cancer Lett. 2005 Apr 8;220(2):197-210.
9 Estrogenic endocrine disruptive components interfere with calcium handling and differentiation of human trophoblast cells. J Cell Biochem. 2003 Jul 1;89(4):755-70.
10 Devenport MH, Crook D, Wynn V, Lees LJ "Metabolic effects of low-dose fluconazole in healthy female users and non-users of oral contraceptives." Br J Clin Pharmacol 27 (1989): 851-9. [PMID: 2547410]
11 Cerner Multum, Inc. "Australian Product Information.".
12 Product Information. Ketek (telithromycin). Aventis Pharmaceuticals, Bridgewater, NJ.
13 Product Information. Tykerb (lapatinib). Novartis Pharmaceuticals, East Hanover, NJ.
14 Product Information. Emend (aprepitant). Merck & Company Inc, West Point, PA.
15 Adson DE, Kotlyar M "A probable interaction between a very low-dose oral contraceptive and the antidepressant nefazodone: a case report." J Clin Psychopharmacol 21 (2001): 618-9. [PMID: 11763013]
16 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
17 Product Information. Dantrium (dantrolene). Procter and Gamble Pharmaceutic, Cincinnati, OH.
18 Galbraith RA, Michnovicz JJ "The effects of cimetidine on the oxidative metabolism of estradiol." N Engl J Med 321 (1989): 269-74. [PMID: 2747769]
19 Product Information. Norvir (ritonavir). Abbott Pharmaceutical, Abbott Park, IL.
20 Product Information. Vaprisol (conivaptan). Cumberland Pharmaceuticals Inc, Nashville, TN.
21 Arafah BM "Increased need for thyroxine in women with hypothyroidism during estrogen therapy." N Engl J Med 344 (2001): 1743-9. [PMID: 11396440]
22 Doherty MM, Charman WN "The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?" Clin Pharmacokinet 41 (2002): 235-53. [PMID: 11978143]
23 Koch-Weser J, Sellers EM "Drug interactions with coumarin anticoagulants (second of two parts)." N Engl J Med 285 (1971): 547-58. [PMID: 4397794]