Details of the Drug

General Information of Drug (ID: DMBSXI0)

Drug Name
Dienestrol
Synonyms
Agaldog; Cycladiene; Dehydrostilbestrol; Dehydrostilboestrol; Dienesterol; Dienestrolo; Dienestrolum; Dienoestrol; Dienol; Dinestrol; Dinovex; Estragard; Estraguard; Estrodienol; Estroral; Follidiene; Follormon; Gynefollin; Hormofemin; Isodienestrol; Oestrasid; Oestrodiene; Oestrodienol; Oestroral; Oestrovis; Restrol; Retalon; Sexadien; Synestrol; Teserene; Willnestrol; Dienestrolo [DCIT]; Dienoestrol [Nonsteroidal oestrogens]; Dienoestrol bp; Alpha-Dienestrol; DV (TN); Dienestrolum [INN-Latin]; Para-Dien; Restrol, Dienestrol; Dienestrol (E,E); Dienestrol (USP/INN); Dienestrol, (E,E)-Isomer; P,p'-(Diethylideneethylene)diphenol; Para,para'-(Diethylideneethylene)diphenol; Di(p-oxyphenyl)-2,4-hexadiene; Di(para-oxyphenyl)-2,4-hexadiene; Phenol, 4,4'-(1,2-diethylidene-1,2-ethanediyl)bis-, (E,E-(9CI); (E,E)-Dienestrol; 3,4-Bis(4-hydroxyphenyl)-2,4-hexadiene; 3,4-Bis(p-hydroxyphenyl)-2,4-hexadiene; 3,4-Bis(para-hydroxyphenyl)-2,4-hexadiene; 4,4'-(1,2-Diethylidene-1,2-ethanediyl)bisphenol; 4,4'-(2E,4E)-hexa-2,4-diene-3,4-diyldiphenol; 4,4'-(Diethylideneethylene)diphenol; 4,4'-Dihydroxy-gamma,delta-diphenyl-beta,delta-hexadiene; 4,4'-Hydroxy-gamma,delta-diphenyl-beta,delta-hexadiene; 4,4'-hexa-2,4-diene-3,4-diyldiphenol; 4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
Indication
Disease Entry ICD 11 Status REF
Atrophic vaginitis GA30.2 Approved [1]
Dyspareunia GA12 Approved [2]
Obsolete atrophic vulva N.A. Approved [2]
Therapeutic Class
Estrogens
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 266.3
Logarithm of the Partition Coefficient (xlogp) 5.4
Rotatable Bond Count (rotbonds) 3
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
C18H18O2
IUPAC Name
4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
Canonical SMILES
C/C=C(/C(=C/C)/C1=CC=C(C=C1)O)\\C2=CC=C(C=C2)O
InChI
InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
InChIKey
NFDFQCUYFHCNBW-SCGPFSFSSA-N
Cross-matching ID
PubChem CID
667476
ChEBI ID
CHEBI:4518
CAS Number
13029-44-2
DrugBank ID
DB00890
TTD ID
D09ZQN
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD 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 [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [4]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [5]
Nuclear receptor subfamily 1 group I member 3 (NR1I3) OTS3SGH7 NR1I3_HUMAN Gene/Protein Processing [6]
Sex hormone-binding globulin (SHBG) OTPWU5IW SHBG_HUMAN Protein Interaction/Cellular Processes [7]
Sulfotransferase 1E1 (SULT1E1) OTGPJ517 ST1E1_HUMAN Gene/Protein Processing [8]
UDP-glucuronosyltransferase 2B15 OTABTFU2 UDB15_HUMAN Regulation of Drug Effects [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Dienestrol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Posaconazole DMUL5EW Moderate Decreased metabolism of Dienestrol caused by Posaconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [10]
Clarithromycin DM4M1SG Moderate Decreased metabolism of Dienestrol caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [11]
Telithromycin DMZ4P3A Moderate Decreased metabolism of Dienestrol caused by Telithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [12]
Tucatinib DMBESUA Moderate Decreased metabolism of Dienestrol caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [13]
Atorvastatin DMF28YC Minor Decreased metabolism of Dienestrol caused by Atorvastatin mediated inhibition of CYP450 enzyme. Cardiovascular disease [BA00-BE2Z] [14]
MK-8228 DMOB58Q Moderate Decreased metabolism of Dienestrol caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [11]
Nefazodone DM4ZS8M Moderate Decreased metabolism of Dienestrol caused by Nefazodone mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [15]
Dantrolene DM1D8XY Major Increased risk of hepatotoxicity by the combination of Dienestrol and Dantrolene. Fever [MG26] [16]
Tazemetostat DMWP1BH Moderate Increased metabolism of Dienestrol caused by Tazemetostat mediated induction of CYP450 enzyme. Follicular lymphoma [2A80] [17]
Itraconazole DMCR1MV Moderate Decreased metabolism of Dienestrol caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [10]
Miconazole DMPMYE8 Moderate Decreased metabolism of Dienestrol caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [10]
Ketoconazole DMPZI3Q Moderate Decreased metabolism of Dienestrol caused by Ketoconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [10]
ABT-450 DMFW860 Major Decreased metabolism of Dienestrol caused by ABT-450 mediated inhibition of UGT. Hepatitis virus infection [1E50-1E51] [18]
Tipranavir DM8HJX6 Moderate Increased risk of skin rash by the combination of Dienestrol and Tipranavir. Human immunodeficiency virus disease [1C60-1C62] [19]
Saquinavir DMG814N Moderate Decreased metabolism of Dienestrol caused by Saquinavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Darunavir DMN3GCH Moderate Decreased metabolism of Dienestrol caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [20]
Carfilzomib DM48K0X Major Additive thrombogenic effects by the combination of Dienestrol and Carfilzomib. Multiple myeloma [2A83] [21]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Dienestrol caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [22]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Dienestrol caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [23]
Voxelotor DMCS6M5 Moderate Decreased metabolism of Dienestrol caused by Voxelotor mediated inhibition of CYP450 enzyme. Sickle-cell disorder [3A51] [24]
⏷ Show the Full List of 20 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: 7160).
2 Dienestrol FDA Label
3 Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. Bone. 2009 Jan;44(1):102-12.
4 Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.
5 Profiling of the Tox21 10K compound library for agonists and antagonists of the estrogen receptor alpha signaling pathway. Sci Rep. 2014 Jul 11;4:5664. doi: 10.1038/srep05664.
6 Agonistic effects of diverse xenobiotics on the constitutive androstane receptor as detected in a recombinant yeast-cell assay. Toxicol In Vitro. 2018 Feb;46:335-349. doi: 10.1016/j.tiv.2017.09.014. Epub 2017 Sep 18.
7 Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and -fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27.
8 Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase. Anal Biochem. 2006 Oct 1;357(1):85-92.
9 Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. Drug Metab Dispos. 1994 Sep-Oct;22(5):799-805.
10 Lazar JD, Wilner KD "Drug interactions with fluconazole." Rev Infect Dis 12 Suppl 3 (1990): s327-33. [PMID: 2330488]
11 Cerner Multum, Inc. "Australian Product Information.".
12 Product Information. Ketek (telithromycin). Aventis Pharmaceuticals, Bridgewater, NJ.
13 Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA.
14 Product Information. Lipitor (atorvastatin). Parke-Davis, Morris Plains, NJ.
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 Fuhr U, Maier-Bruggemann A, Blume H, et al. "Grapefruit juice increases oral nimodipine bioavailability." Int J Clin Pharmacol Ther 36 (1998): 126-32. [PMID: 9562227]
17 Gunston GD, Mehta U "Potentially serious drug interactions with grapefruit juice." S Afr Med J 90 (2000): 41. [PMID: 10721388]
18 Product Information. Norvir (ritonavir). Abbott Pharmaceutical, Abbott Park, IL.
19 Canadian Pharmacists Association.
20 Product Information. Prezista (darunavir). Ortho Biotech Inc, Bridgewater, NJ.
21 Product Information. Kyprolis (carfilzomib). Onyx Pharmaceuticals Inc, South San Francisco, CA.
22 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
23 Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
24 Bailey DG, Arnold JMO, Spence JD "Grapefruit juice and drugs - how significant is the interaction." Clin Pharmacokinet 26 (1994): 91-8. [PMID: 8162660]