General Information of Drug (ID: DMTMLXU)

Drug Name
4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenol Drug Info
Synonyms
91221-46-4; 1,1-Bis(4-hydroxyphenyl)-2-phenylbut-1-ene; 1,1-Bis(4-hydroxyphenyl)-2-phenyl-1-butene; 4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenol; CHEMBL149791; 4,4'-(2-phenylbut-1-ene-1,1-diyl)diphenol; Tamoxifen bis-phenol; 1,1-Bhpe; Tamoxifenbisphenol; AC1L1YAG; SCHEMBL639225; CTK5G9076; DTXSID50238452; BPKSDMHGDYTXLI-UHFFFAOYSA-N; ZINC1849484; BDBM50121317; AKOS030254689; KB-09832; 4,4'-(2-Phenyl-1-butenylidene)bisphenol; B5114; FT-0663304; Phenol, 4,4'-(2-phenyl-1-butenylidene)bis-
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
63059
CAS Number
CAS 91221-46-4
TTD Drug ID
DMTMLXU

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Drug(s) Targeting Estrogen receptor (ESR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [3]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [4]
Estrone DM5T6US Acne vulgaris ED80 Approved [4]
Estradiol Valerate DM8MC6O Hormone replacement therapy 8E01 Approved [5]
Estradiol Acetate DM07U2A Hormone replacement therapy 8E01 Approved [5]
Estradiol Cypionate DM27Z5T Hormone replacement therapy 8E01 Approved [5]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [6]
Raloxifene DMDKF3M Osteoporosis FB83.0 Approved [7]
Ospemifene DMC4GEI Dyspareunia GA12 Approved [8]
Toremifene DMQYUWG Breast cancer 2C60-2C65 Approved [9]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [10]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [11]
Methotrexate DM2TEOL Anterior urethra cancer Approved [12]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [13]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [14]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [15]
Fedratinib DM4ZBK6 Myelofibrosis 2A20.2 Approved [16]
Panobinostat DM58WKG Chronic graft versus host disease Approved [17]
Pyrimethamine DM5X7VY Malaria 1F40-1F45 Approved [16]
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Annexin A1 (ANXA1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Quercetin DM3NC4M Obesity 5B81 Approved [18]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [14]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [19]
Panobinostat DM58WKG Chronic graft versus host disease Approved [17]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [20]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [21]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [22]
Acocantherin DM7JT24 Atrial fibrillation BC81.3 Approved [23]
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [14]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [24]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [25]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [26]
Crizotinib DM4F29C Non-small-cell lung cancer 2C25.Y Approved [27]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [28]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [29]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [30]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [31]
Enzalutamide DMGL19D Prostate cancer 2C82.0 Approved [32]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [33]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [2]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [34]
Panobinostat DM58WKG Chronic graft versus host disease Approved [17]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [35]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [36]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [37]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [38]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [2]
Vorinostat DMWMPD4 Adult acute monocytic leukemia Approved [17]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [39]
PDX-101 DM6OC53 Plasma cell myeloma 2A83.1 Phase 2 [17]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Selenium DM25CGV N. A. N. A. Approved [40]
Pentosan Polysulfate DM2HRKE Interstitial cystitis GC00.3 Approved [41]
Methotrexate DM2TEOL Anterior urethra cancer Approved [42]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [43]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [34]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [28]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [44]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [45]
Leflunomide DMR8ONJ Arthritis FA20 Approved [46]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [24]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Bepridil DM0RKS4 Chronic/stable angina BA40.1 Approved [47]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [48]
Selenium DM25CGV N. A. N. A. Approved [49]
Ribavirin DMEYLH9 Hepatitis C virus infection 1E51.1 Approved [50]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [51]
Methotrexate DM2TEOL Anterior urethra cancer Approved [52]
Quercetin DM3NC4M Obesity 5B81 Approved [53]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [54]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [55]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [56]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [31]
Afimoxifene DMFORDT Breast cancer 2C60-2C65 Phase 2 [2]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [57]
PMID20638279C11 DMFHS4V Discovery agent N.A. Investigative [58]
bisphenol A DM2ZLD7 Discovery agent N.A. Investigative [25]
acetaldehyde DMJFKG4 Discovery agent N.A. Investigative [59]
2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE DMNQL17 Discovery agent N.A. Investigative [60]
Deguelin DMXT7WG Esophageal squamous cell carcinoma 2E60.1 Investigative [61]
⏷ Show the Full List of 8 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Colchicine DM2POTE Acute gout flare FA25.0 Approved [62]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [63]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [31]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [64]
Decitabine DMQL8XJ Acute myelogenous leukaemia 2A41 Approved [65]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [62]
Arsenic DMTL2Y1 N. A. N. A. Approved [66]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [2]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [67]
Adenine DMZLHKJ Malnutrition 5B50-5B71 Approved [62]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Protein lifeguard 2 (FAIM2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [48]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [14]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [31]
Arsenic DMTL2Y1 N. A. N. A. Approved [68]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [2]
Afimoxifene DMFORDT Breast cancer 2C60-2C65 Phase 2 [2]
(+)-JQ1 DM1CZSJ Testicular cancer 2C80 Phase 1 [69]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [57]
Milchsaure DM462BT Pruritus EC90 Investigative [70]
⏷ Show the Full List of 9 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [19]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [71]
Testosterone DM7HUNW Hot flushes GA30 Approved [72]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [72]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [24]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [31]
Menthol DMG2KW7 Back pain ME84.Z Approved [73]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [74]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [75]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [24]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Tumor protein 63 (TP63)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [25]
Quercetin DM3NC4M Obesity 5B81 Approved [76]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [77]
Panobinostat DM58WKG Chronic graft versus host disease Approved [78]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [79]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [80]
Melphalan DMOLNHF Hematologic disease 3C0Z Approved [81]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [74]
Topotecan DMP6G8T Central nervous system neoplasm Approved [82]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [83]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Annexin A1 (ANXA1) OT5OFDJC ANXA1_HUMAN Gene/Protein Processing [2]
Caspase recruitment domain-containing protein 6 (CARD6) OTEI1PJ1 CARD6_HUMAN Gene/Protein Processing [2]
Metabotropic glutamate receptor 4 (GRM4) OT5ID1DZ GRM4_HUMAN Gene/Protein Processing [2]
Metalloproteinase inhibitor 3 (TIMP3) OTDGQAD1 TIMP3_HUMAN Gene/Protein Processing [2]
Paired box protein Pax-7 (PAX7) OTDMQRPO PAX7_HUMAN Gene/Protein Processing [2]
Pleckstrin homology domain-containing family F member 1 (PLEKHF1) OT9OL16U PKHF1_HUMAN Gene/Protein Processing [2]
Protein lifeguard 2 (FAIM2) OT6QINVO LFG2_HUMAN Gene/Protein Processing [2]
Suppressor of cytokine signaling 3 (SOCS3) OTY183WJ SOCS3_HUMAN Gene/Protein Processing [2]
Tumor necrosis factor ligand superfamily member 10 (TNFSF10) OT4PXBTA TNF10_HUMAN Gene/Protein Processing [2]
Tumor protein 63 (TP63) OT0WOOKQ P63_HUMAN Gene/Protein Processing [2]

References

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27 Structure based drug design of crizotinib (PF-02341066), a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK). J Med Chem. 2011 Sep 22;54(18):6342-63. doi: 10.1021/jm2007613. Epub 2011 Aug 18.
28 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
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30 Imatinib mesylate inhibits T-cell proliferation in vitro and delayed-type hypersensitivity in vivo. Blood. 2004 Aug 15;104(4):1094-9. doi: 10.1182/blood-2003-12-4266. Epub 2004 Apr 20.
31 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
32 LSD1 activates a lethal prostate cancer gene network independently of its demethylase function. Proc Natl Acad Sci U S A. 2018 May 1;115(18):E4179-E4188.
33 Sorafenib induces cell death in chronic lymphocytic leukemia by translational downregulation of Mcl-1. Leukemia. 2011 May;25(5):838-47. doi: 10.1038/leu.2011.2. Epub 2011 Feb 4.
34 Development of a neural teratogenicity test based on human embryonic stem cells: response to retinoic acid exposure. Toxicol Sci. 2011 Dec;124(2):370-7.
35 Integrated analysis of rifampicin-induced microRNA and gene expression changes in human hepatocytes. Drug Metab Pharmacokinet. 2014;29(4):333-40.
36 Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
37 Clinical determinants of response to irinotecan-based therapy derived from cell line models. Clin Cancer Res. 2008 Oct 15;14(20):6647-55.
38 Blood transcript immune signatures distinguish a subset of people with elevated serum ALT from others given acetaminophen. Clin Pharmacol Ther. 2016 Apr;99(4):432-41.
39 Gene Expression Regulation and Pathway Analysis After Valproic Acid and Carbamazepine Exposure in a Human Embryonic Stem Cell-Based Neurodevelopmental Toxicity Assay. Toxicol Sci. 2015 Aug;146(2):311-20. doi: 10.1093/toxsci/kfv094. Epub 2015 May 15.
40 Inhibition of invasion and induction of apoptosis by selenium in human malignant brain tumour cells in vitro. Int J Oncol. 2007 May;30(5):1263-71.
41 Pentosan polysulfate decreases proliferation and extracellular matrix deposition by vascular smooth muscle cells isolated from failed hemodialysis access grafts. Clin Nephrol. 2000 Aug;54(2):121-7.
42 Functional gene expression profile underlying methotrexate-induced senescence in human colon cancer cells. Tumour Biol. 2011 Oct;32(5):965-76.
43 Rofecoxib regulates the expression of genes related to the matrix metalloproteinase pathway in humans: implication for the adverse effects of cyclooxygenase-2 inhibitors. Clin Pharmacol Ther. 2006 Apr;79(4):303-15. doi: 10.1016/j.clpt.2005.12.306.
44 Arsenic trioxide induces different gene expression profiles of genes related to growth and apoptosis in glioma cells dependent on the p53 status. Mol Biol Rep. 2008 Sep;35(3):421-9.
45 Large-scale in silico and microarray-based identification of direct 1,25-dihydroxyvitamin D3 target genes. Mol Endocrinol. 2005 Nov;19(11):2685-95.
46 Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
47 Amiodarone sensitizes human glioma cells but not astrocytes to TRAIL-induced apoptosis via CHOP-mediated DR5 upregulation. Neuro Oncol. 2011 Mar;13(3):267-79. doi: 10.1093/neuonc/noq195. Epub 2011 Feb 3.
48 Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells. Arch Biochem Biophys. 2006 Nov 1;455(1):48-60.
49 Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
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53 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.
54 Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
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56 Gene microarray analysis of human renal cell carcinoma: the effects of HDAC inhibition and retinoid treatment. Cancer Biol Ther. 2008 Oct;7(10):1607-18.
57 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
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59 Transcriptome profile analysis of saturated aliphatic aldehydes reveals carbon number-specific molecules involved in pulmonary toxicity. Chem Res Toxicol. 2014 Aug 18;27(8):1362-70.
60 Preferential induction of the AhR gene battery in HepaRG cells after a single or repeated exposure to heterocyclic aromatic amines. Toxicol Appl Pharmacol. 2010 Nov 15;249(1):91-100.
61 Neurotoxicity and underlying cellular changes of 21 mitochondrial respiratory chain inhibitors. Arch Toxicol. 2021 Feb;95(2):591-615. doi: 10.1007/s00204-020-02970-5. Epub 2021 Jan 29.
62 Utilization of CDKN1A/p21 gene for class discrimination of DNA damage-induced clastogenicity. Toxicology. 2014 Jan 6;315:8-16. doi: 10.1016/j.tox.2013.10.009. Epub 2013 Nov 6.
63 Expression profile analysis of colon cancer cells in response to sulindac or aspirin. Biochem Biophys Res Commun. 2002 Mar 29;292(2):498-512.
64 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
65 Epigenetic silencing of novel tumor suppressors in malignant melanoma. Cancer Res. 2006 Dec 1;66(23):11187-93. doi: 10.1158/0008-5472.CAN-06-1274.
66 Drinking-water arsenic exposure modulates gene expression in human lymphocytes from a U.S. population. Environ Health Perspect. 2008 Apr;116(4):524-31. doi: 10.1289/ehp.10861.
67 Bringing in vitro analysis closer to in vivo: studying doxorubicin toxicity and associated mechanisms in 3D human microtissues with PBPK-based dose modelling. Toxicol Lett. 2018 Sep 15;294:184-192.
68 Association of Arsenic Exposure with Whole Blood DNA Methylation: An Epigenome-Wide Study of Bangladeshi Adults. Environ Health Perspect. 2019 May;127(5):57011. doi: 10.1289/EHP3849. Epub 2019 May 28.
69 CCAT1 is an enhancer-templated RNA that predicts BET sensitivity in colorectal cancer. J Clin Invest. 2016 Feb;126(2):639-52.
70 Transcriptional profiling of lactic acid treated reconstructed human epidermis reveals pathways underlying stinging and itch. Toxicol In Vitro. 2019 Jun;57:164-173.
71 THC exposure of human iPSC neurons impacts genes associated with neuropsychiatric disorders. Transl Psychiatry. 2018 Apr 25;8(1):89. doi: 10.1038/s41398-018-0137-3.
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74 Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
75 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.
76 Flavones and flavonols exert cytotoxic effects on a human oesophageal adenocarcinoma cell line (OE33) by causing G2/M arrest and inducing apoptosis. Food Chem Toxicol. 2008 Jun;46(6):2042-53. doi: 10.1016/j.fct.2008.01.049. Epub 2008 Feb 7.
77 Activation of PPAR and inhibition of cell proliferation reduces key proteins associated with the basal subtype of bladder cancer in As3+-transformed UROtsa cells. PLoS One. 2020 Aug 21;15(8):e0237976. doi: 10.1371/journal.pone.0237976. eCollection 2020.
78 Induction of TAp63 by histone deacetylase inhibitors. Biochem Biophys Res Commun. 2010 Jan 22;391(4):1748-51. doi: 10.1016/j.bbrc.2009.12.147. Epub 2009 Dec 30.
79 Identification of vitamin D3 target genes in human breast cancer tissue. J Steroid Biochem Mol Biol. 2016 Nov;164:90-97.
80 Design principles of concentration-dependent transcriptome deviations in drug-exposed differentiating stem cells. Chem Res Toxicol. 2014 Mar 17;27(3):408-20.
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