Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMBSXI0)

Drug Name
Dienestrol Drug Info
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 Approved [2]
Therapeutic Class
Estrogens
Cross-matching ID
PubChem CID
667476
ChEBI ID
CHEBI:4518
CAS Number
CAS 13029-44-2
TTD Drug ID
DMBSXI0

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Estrogen receptor (ESR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [10]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [11]
Estrone DM5T6US Acne vulgaris ED80 Approved [11]
Estradiol Valerate DM8MC6O Hormone replacement therapy 8E01 Approved [12]
Estradiol Acetate DM07U2A Hormone replacement therapy 8E01 Approved [12]
Estradiol Cypionate DM27Z5T Hormone replacement therapy 8E01 Approved [12]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [13]
Raloxifene DMDKF3M Osteoporosis FB83.0 Approved [14]
Ospemifene DMC4GEI Dyspareunia GA12 Approved [15]
Toremifene DMQYUWG Breast cancer 2C60-2C65 Approved [16]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Sulfotransferase 1E1 (SULT1E1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Meclofenamic acid DM05FXR Ankylosing spondylitis FA92.0 Approved [17]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [17]
Methotrexate DM2TEOL Anterior urethra cancer Approved [18]
Estrone DM5T6US Acne vulgaris ED80 Approved [8]
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [17]
Ethanol DMDRQZU Chronic pain MG30 Approved [19]
Folic Acid DMEMBJC Colorectal carcinoma Approved [20]
Bosentan DMIOGBU Pulmonary arterial hypertension BB01.0 Approved [21]
Sodium lauryl sulfate DMLJ634 Constipation DD91.1 Approved [22]
Diethylstilbestrol DMN3UXQ Gonorrheal vaginitis GA02 Approved [8]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Estrogen receptor (ESR1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [23]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [24]
Gefitinib DM15F0X Colon adenocarcinoma Approved [25]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [26]
Lapatinib DM3BH1Y Breast cancer 2C60-2C65 Approved [27]
Liraglutide DM3FXPS Non-insulin dependent diabetes 5A11 Approved [28]
Quercetin DM3NC4M Obesity 5B81 Approved [29]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [30]
Procaine DM4LSNE Anaesthesia 9A78.6 Approved [26]
Estrone DM5T6US Acne vulgaris ED80 Approved [31]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Sex hormone-binding globulin (SHBG)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Levonorgestrel DM1DP7T Atypical endometrial hyperplasia Approved [32]
Quercetin DM3NC4M Obesity 5B81 Approved [33]
Fructose DM43AN2 Vomiting MD90 Approved [34]
Oxcarbazepine DM5PU6O Epilepsy 8A60-8A68 Approved [35]
Estrone DM5T6US Acne vulgaris ED80 Approved [7]
Testosterone DM7HUNW Hot flushes GA30 Approved [36]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [37]
Hesperetin DMKER83 High blood cholesterol level 5C80.00 Approved [7]
Masoprocol DMMVNZ0 Prostate cancer 2C82.0 Approved [7]
Diethylstilbestrol DMN3UXQ Gonorrheal vaginitis GA02 Approved [7]
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Drug(s) Affected By Cellular tumor antigen p53 (TP53)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [38]
Methotrexate DM2TEOL Anterior urethra cancer Approved [39]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [40]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [41]
Cidofovir DMA13GD Cytomegalovirus infection 1D82 Approved [42]
Paclitaxel DMLB81S Breast carcinoma Approved [43]
Floxuridine DM04LR2 Colorectal cancer 2B91.Z Approved [44]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [45]
Mechlorethamine DM0CVXA Chronic myelogenous leukaemia 2A20.0 Approved [46]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [47]
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Drug(s) Affected By Nuclear receptor subfamily 1 group I member 3 (NR1I3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [48]
Quercetin DM3NC4M Obesity 5B81 Approved [49]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [50]
Artemether DM48QOT Malaria 1F40-1F45 Approved [51]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [52]
Nefazodone DM4ZS8M Major depressive disorder 6A70.3 Approved [53]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [54]
Estrone DM5T6US Acne vulgaris ED80 Approved [6]
Leflunomide DMR8ONJ Arthritis FA20 Approved [55]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [56]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas
Download the Complete Interaction Atlas for Visualization in Cytoscape

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]

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 Modulators of vascular sex hormone receptors and their effects in estrogen-deficiency states associated with menopause. Recent Pat Cardiovasc Drug Discov. 2008 Nov;3(3):165-86.
11 Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
12 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
13 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8.
14 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. (Target id: 620).
15 Clinical pipeline report, company report or official report of Shionogi (2011).
16 Effect of selective estrogen receptor modulators on cell proliferation and estrogen receptor activities in normal human prostate stromal and epithe... Prostate Cancer Prostatic Dis. 2009;12(4):375-81.
17 Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab. 2006 Oct;7(7):745-53.
18 Methotrexate induction of human sulfotransferases in Hep G2 and Caco-2 cells. J Appl Toxicol. 2005 Sep-Oct;25(5):354-60.
19 Solvent effect on cDNA-expressed human sulfotransferase (SULT) activities in vitro. Drug Metab Dispos. 2003 Nov;31(11):1300-5.
20 Folic acid supplementation dysregulates gene expression in lymphoblastoid cells--implications in nutrition. Biochem Biophys Res Commun. 2011 Sep 9;412(4):688-92. doi: 10.1016/j.bbrc.2011.08.027. Epub 2011 Aug 16.
21 Omics-based responses induced by bosentan in human hepatoma HepaRG cell cultures. Arch Toxicol. 2018 Jun;92(6):1939-1952.
22 CXCL14 downregulation in human keratinocytes is a potential biomarker for a novel in vitro skin sensitization test. Toxicol Appl Pharmacol. 2020 Jan 1;386:114828. doi: 10.1016/j.taap.2019.114828. Epub 2019 Nov 14.
23 Estrogen-like activity of metals in MCF-7 breast cancer cells. Endocrinology. 2003 Jun;144(6):2425-36. doi: 10.1210/en.2002-221054.
24 Cross-talk between non-genomic and genomic signalling pathways--distinct effect profiles of environmental estrogens. Toxicol Appl Pharmacol. 2010 Jun 1;245(2):160-70. doi: 10.1016/j.taap.2010.02.015. Epub 2010 Mar 4.
25 Bidirectional cross talk between ERalpha and EGFR signalling pathways regulates tamoxifen-resistant growth. Breast Cancer Res Treat. 2006 Mar;96(2):131-46. doi: 10.1007/s10549-005-9070-2. Epub 2005 Oct 27.
26 Sensitivity of human dental pulp cells to eighteen chemical agents used for endodontic treatments in dentistry. Odontology. 2013 Jan;101(1):43-51.
27 The dual ErbB1/ErbB2 inhibitor, lapatinib (GW572016), cooperates with tamoxifen to inhibit both cell proliferation- and estrogen-dependent gene expression in antiestrogen-resistant breast cancer. Cancer Res. 2005 Jan 1;65(1):18-25.
28 Antitumoral activity of liraglutide, a new DNMT inhibitor in breast cancer cells in vitro and in vivo. Chem Biol Interact. 2021 Nov 1;349:109641. doi: 10.1016/j.cbi.2021.109641. Epub 2021 Sep 14.
29 Estrogen receptor alpha mediates the proliferative but not the cytotoxic dose-dependent effects of two major phytoestrogens on human breast cancer cells. Mol Pharmacol. 2001 Sep;60(3):595-602.
30 Novel retinoic acid metabolism blocking agents have potent inhibitory activities on human breast cancer cells and tumour growth. Br J Cancer. 2007 Apr 23;96(8):1204-15. doi: 10.1038/sj.bjc.6603705. Epub 2007 Mar 27.
31 Prediction of the combined effects of multiple estrogenic chemicals on MCF-7 human breast cancer cells and a preliminary molecular exploration of the estrogenic proliferative effects and related gene expression. Ecotoxicol Environ Saf. 2018 Sep 30;160:1-9. doi: 10.1016/j.ecoenv.2018.05.025. Epub 2018 May 21.
32 Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. Contraception. 2003 Feb;67(2):93-9. doi: 10.1016/s0010-7824(02)00473-0.
33 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
34 Monosaccharide-induced lipogenesis regulates the human hepatic sex hormone-binding globulin gene. J Clin Invest. 2007 Dec;117(12):3979-87. doi: 10.1172/JCI32249.
35 Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy. Neurology. 2001 Jan 9;56(1):31-6. doi: 10.1212/wnl.56.1.31.
36 Testosterone or 17{beta}-estradiol exposure reveals sex-specific effects on glucose and lipid metabolism in human myotubes. J Endocrinol. 2011 Aug;210(2):219-29. doi: 10.1530/JOE-10-0497. Epub 2011 Jun 1.
37 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
38 p53-R175H mutant gains new function in regulation of doxorubicin-induced apoptosis. Int J Cancer. 2005 Apr 10;114(3):331-6. doi: 10.1002/ijc.20818.
39 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
40 Azidothymidine and cisplatin increase p14ARF expression in OVCAR-3 ovarian cancer cell line. Toxicol Appl Pharmacol. 2006 Oct 1;216(1):89-97. doi: 10.1016/j.taap.2006.04.015. Epub 2006 May 19.
41 Quantitative analysis of gene expression changes in response to genotoxic compounds. Toxicol In Vitro. 2017 Mar;39:15-28. doi: 10.1016/j.tiv.2016.11.004. Epub 2016 Nov 5.
42 Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells. Oncol Res. 2000;12(9-10):397-408. doi: 10.3727/096504001108747855.
43 Gallic acid potentiates the apoptotic effect of paclitaxel and carboplatin via overexpression of Bax and P53 on the MCF-7 human breast cancer cell line. J Biochem Mol Toxicol. 2021 Feb;35(2):e22638. doi: 10.1002/jbt.22638. Epub 2020 Oct 1.
44 Regulation of human dUTPase gene expression and p53-mediated transcriptional repression in response to oxaliplatin-induced DNA damage. Nucleic Acids Res. 2009 Jan;37(1):78-95. doi: 10.1093/nar/gkn910. Epub 2008 Nov 16.
45 Role of miRNA in the regulation of cannabidiol-mediated apoptosis in neuroblastoma cells. Oncotarget. 2019 Jan 1;10(1):45-59. doi: 10.18632/oncotarget.26534. eCollection 2019 Jan 1.
46 Nitrogen Mustard Alkylates and Cross-Links p53 in Human Keratinocytes. Chem Res Toxicol. 2022 Apr 18;35(4):636-650. doi: 10.1021/acs.chemrestox.1c00420. Epub 2022 Mar 21.
47 Fulvestrant induces resistance by modulating GPER and CDK6 expression: implication of methyltransferases, deacetylases and the hSWI/SNF chromatin remodelling complex. Br J Cancer. 2013 Nov 12;109(10):2751-62. doi: 10.1038/bjc.2013.583. Epub 2013 Oct 29.
48 Identification of HMG-CoA reductase inhibitors as activators for human, mouse and rat constitutive androstane receptor. Drug Metab Dispos. 2005 Jul;33(7):924-9.
49 Bioactive terpenoids and flavonoids from Ginkgo biloba extract induce the expression of hepatic drug-metabolizing enzymes through pregnane X receptor, constitutive androstane receptor, and aryl hydrocarbon receptor-mediated pathways. Pharm Res. 2009 Apr;26(4):872-82.
50 Species-specific toxicity of diclofenac and troglitazone in primary human and rat hepatocytes. Chem Biol Interact. 2009 Apr 15;179(1):17-24.
51 Fetal bovine serum and human constitutive androstane receptor: evidence for activation of the SV23 splice variant by artemisinin, artemether, and arteether in a serum-free cell culture system. Toxicol Appl Pharmacol. 2014 Jun 1;277(2):221-30. doi: 10.1016/j.taap.2014.03.023. Epub 2014 Apr 12.
52 Constitutive androstane/active receptor is a target of retinoic acid receptor in humans. Biochem Pharmacol. 2010 Jul 1;80(1):129-35. doi: 10.1016/j.bcp.2010.02.023. Epub 2010 Mar 6.
53 Robustness testing and optimization of an adverse outcome pathway on cholestatic liver injury. Arch Toxicol. 2020 Apr;94(4):1151-1172. doi: 10.1007/s00204-020-02691-9. Epub 2020 Mar 10.
54 Expression and inducibility of cytochrome P450s (CYP1A1, 2B6, 2E1, 3A4) in human cord blood CD34(+) stem cell-derived differentiating neuronal cells. Toxicol Sci. 2012 Oct;129(2):392-410.
55 Teriflunomide is an indirect human constitutive androstane receptor (CAR) activator interacting with epidermal growth factor (EGF) signaling. Front Pharmacol. 2018 Oct 11;9:993.
56 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.