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
• Drug Type: Small molecular drug
• #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 []

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Congenital, familial and genetic disorders	Not Available	GPX1	OTE2O72Q	[2]

• 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: CHEBI:41922
  CAS Number: 56-53-1
  DrugBank ID: DB00255
  TTD ID: D0Y2NE
  VARIDT ID: DR00922
  INTEDE ID: DR0492

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	[3]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[4]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[5]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[6]

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	[7]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1 (PLCB1)	OT9HYT7A	PLCB1_HUMAN	Gene/Protein Processing	[8]
14-3-3 protein beta/alpha	OTGBS3RF	1433B_HUMAN	Gene/Protein Processing	[9]
17-beta-hydroxysteroid dehydrogenase type 1 (HSD17B1)	OT6EBDHM	DHB1_HUMAN	Gene/Protein Processing	[10]
26S proteasome non-ATPase regulatory subunit 1 (PSMD1)	OTW258OV	PSMD1_HUMAN	Gene/Protein Processing	[7]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1)	OTNAZVKB	3BHS1_HUMAN	Gene/Protein Processing	[10]
3-hydroxyisobutyrate dehydrogenase, mitochondrial (HIBADH)	OTCMMMIZ	3HIDH_HUMAN	Gene/Protein Processing	[7]
4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT5 (FUT5)	OTOPGL9M	FUT5_HUMAN	Gene/Protein Processing	[8]
5-hydroxymethyl-dUMP N-hydrolase (DNPH1)	OTEZVTI1	DNPH1_HUMAN	Gene/Protein Processing	[9]
A disintegrin and metalloproteinase with thrombospondin motifs 9 (ADAMTS9)	OTV3Q0DS	ATS9_HUMAN	Gene/Protein Processing	[8]

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

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

References

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