4-hydroxy-n-desmethyltamoxifen profile

4-hydroxy-N-desmethyltamoxifen: metabolite of tamoxifen in human bile [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	10090750
CHEMBL ID	1093458
CHEBI ID	80555
SCHEMBL ID	10107920
MeSH ID	M0156220

Synonym
46af8680rc ,
phenol, 4-(1-(4-(2-(methylamino)ethoxy]phenyl)-2-phenyl-1-butenyl)-, (z)-
nsc 749798
unii-46af8680rc
110025-28-0
4ohndtam
4-hydroxy-n-desmethyltamoxifen
endoxifen
112093-28-4
4-hydroxy-n-desmethyl tamoxifen
nsc746494
nsc-746494
z-endoxifen
CHEMBL1093458
n-desmethyl-4-hydroxytamoxifen
chebi:80555 ,
nsc-749798
phenol, 4-[(1z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-
4-hydroxy-n-desmethyl-tamoxifen
nsc749798
phenol, 4-((1z)-1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenyl-1-buten-1-yl)-
4-hydroxy-n-desmethyltamoxifen, (z)-isomer
bdbm50435003
endoxifen [who-dd]
SCHEMBL10107920
W-200834
(e/z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol
(z)-endoxifen
(z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol
(e/z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol
endoxifen (z-isomer)
HY-18719E
CS-0028594
DTXSID80149880
J-002363
EX-A645
AKOS030526256
endoxifen z-isomer
MHJBZVSGOZTKRH-IZHYLOQSSA-N
4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
(z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol ,
NCGC00386714-01
4-[(1z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol
BCP15866
4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
Q27149598
mfcd09840374
gtpl10203
4-[(~{z})-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
EX-A1970
endoxifen(e/z=1:1)
4-[(z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
A894656
;4-[(1z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol; 4-hydroxy-n-desmethyltamoxifen; n-desmethyl-4-hydroxytamoxifen;(e/z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol
nsc777380
nsc-777380
BS-42369
endoxifenz-isomer
(z)-4-hydroxy-n-desmethyl tamoxifen(contains up to 10% e isomer)
BE172975
EN300-822190
n-desmethyl-4-hydroxy tamoxifen(approx. 1:1 e/z mixture)
AC-36810

Excerpt	Reference	Relevance
" This is the first study demonstrating that single oral doses of endoxifen are safe and well tolerated and have sufficient bioavailability to reach systemically effective levels in human subjects."	( Endoxifen, a new cornerstone of breast cancer therapy: demonstration of safety, tolerability, and systemic bioavailability in healthy human subjects. Ahmad, A; Ahmad, I; Kale, P; Krishnappa, M; Rane, RC; Shahabuddin, S; Sheikh, S, 2010)	0.36
" A preliminary assessment of their acute aquatic toxicity at two trophic levels by means of quantitative structure-activity relationship models showed that the identified byproducts were up to 110-fold more toxic than the parent compounds."	( Transformation of tamoxifen and its major metabolites during water chlorination: Identification and in silico toxicity assessment of their disinfection byproducts. Barceló, D; López de Alda, M; Negreira, N; Regueiro, J, 2015)	0.42
" Whether such tamoxifen dose escalation is effective and safe in view of long-term toxic effects is uncertain and needs to be explored."	( CYP2D6 genotype- and endoxifen-guided tamoxifen dose escalation increases endoxifen serum concentrations without increasing side effects. Dezentjé, VO; Dieudonné, AS; Gelderblom, H; Guchelaar, HJ; Hartigh den, J; Maartense, E; Neven, P; Nortier, JW; Opdam, FL; Putter, H; Smorenburg, CH; Van de Velde, CJ; Van der Straaten, T; Vree, R, 2015)	0.42
" Endoxifen, which is toxic to aquatic animals, has been detected in wastewater treatment plant (WWTP) effluent."	( Photodegradation of (E)- and (Z)-Endoxifen in water by ultraviolet light: Efficiency, kinetics, by-products, and toxicity assessment. Delorme, A; Khan, E; Martin, MA; McEvoy, J; Sivaguru, J; Sonthiphand, P, 2020)	0.56

Excerpt	Reference	Relevance
"Population pharmacokinetic models were developed for dextromethorphan, tamoxifen and their metabolites."	( Population pharmacokinetic modelling to assess the impact of CYP2D6 and CYP3A metabolic phenotypes on the pharmacokinetics of tamoxifen and endoxifen. Beijnen, JH; Binkhorst, L; de Bruijn, P; de Graan, AJ; Huitema, AD; Mathijssen, RH; ter Heine, R, 2014)	0.4
"The pharmacokinetic-pharmacodynamic model was established by integrating a four compartments pharmacokinetics model and a pharmacodynamic model, the first one include central compartment and peripheral compartment both of which contain tamoxifen and endoxifen."	( A Pharmacokinetic-Pharmacodynamic Model of Tamoxifen and Endoxifen to Predict Their Distribution and Effects on Inhibition of Tumor Growth. Chen, Y; Liao, J; Sun, Q; Yuan, S, 2017)	0.46
" The parameters of the pharmacodynamic model, which characterized the tumor growth, revealed the patterns of tamoxifen's anti-tumor functions."	( A Pharmacokinetic-Pharmacodynamic Model of Tamoxifen and Endoxifen to Predict Their Distribution and Effects on Inhibition of Tumor Growth. Chen, Y; Liao, J; Sun, Q; Yuan, S, 2017)	0.46
" We developed a population pharmacokinetic (PopPK) model for tamoxifen and six metabolites to determine clinically relevant factors of ENDO exposure."	( Model-Based Quantification of Impact of Genetic Polymorphisms and Co-Medications on Pharmacokinetics of Tamoxifen and Six Metabolites in Breast Cancer. Arellano, C; Bernard-Marty, C; Boyer, JC; Chatelut, E; Dalenc, F; Debled, M; Delmas, C; Dohollou, N; Evrard, A; Filleron, T; Jacot, W; Laharie-Mineur, H; Le Morvan, V; Puszkiel, A; Robert, J; Roché, H; Thomas, F; Vachoux, C; Venat-Bouvet, L; White-Koning, M, 2021)	0.62
"The purpose of this study was to develop and validate a population pharmacokinetic model for Z-endoxifen in patients with advanced solid tumors and to identify clinical variables that influence pharmacokinetic parameters."	( Population Pharmacokinetics of Z-Endoxifen in Patients With Advanced Solid Tumors. Adjei, AA; Ames, MM; Buhrow, SA; Covey, JM; Goetz, MP; Koubek, EJ; Larson, TR; McGovern, RM; Ralya, AT; Reid, JM; Takebe, N, 2022)	0.72
" Our aim is to develop a population pharmacokinetic (POP-PK) model incorporating a continuous CYP2D6 activity scale to support model informed precision dosing (MIPD) of tamoxifen to determine the optimal tamoxifen starting dose."	( Toward model-informed precision dosing for tamoxifen: A population-pharmacokinetic model with a continuous CYP2D6 activity scale. Agema, BC; Buijs, SM; Jager, A; Koch, BCP; Koolen, SLW; Mathijssen, RHJ; Mürdter, TE; Sassen, SDT; Schwab, M; van Schaik, RHN, 2023)	0.91

Excerpt	Reference	Relevance
" This work evaluated the effects of RA alone and in combination with the antiestrogen endoxifen (EDX) on liver mitochondria."	( Effects of all-trans-retinoic acid on the permeability transition and bioenergetic functions of rat liver mitochondria in combination with endoxifen. Custódio, JB; Ribeiro, MP; Santos, AE; Santos, MS, 2013)	0.39
"RA-induced hepatotoxicity may be related with induction of MPT and alterations in bioenergetic parameters; the combination with EDX, which reduces mitochondrial dysfunction and synergistically potentiates the anticancer activity, may provide a safer therapeutic strategy."	( Effects of all-trans-retinoic acid on the permeability transition and bioenergetic functions of rat liver mitochondria in combination with endoxifen. Custódio, JB; Ribeiro, MP; Santos, AE; Santos, MS, 2013)	0.39
" Antidepressants (ADs), which are often coprescribed to patients receiving tamoxifen, are also metabolized by CYP2D6 and evidence suggests that a drug-drug interaction between these agents adversely affects the outcome of tamoxifen therapy by inhibiting endoxifen formation."	( Application of Mice Humanized for CYP2D6 to the Study of Tamoxifen Metabolism and Drug-Drug Interaction with Antidepressants. Henderson, CJ; MacLeod, AK; McLaughlin, LA; Wolf, CR, 2017)	0.46
"The in vitro results suggest that mistletoe preparations can be used in combination with tamoxifen without the risk of HDIs."	( Absence of herb-drug interactions of mistletoe with the tamoxifen metabolite (E/Z)-endoxifen and cytochrome P450 3A4/5 and 2D6 in vitro. Baumgartner, S; Hamburger, M; Kunz, M; Oufir, M; Regueiro, U; Urech, K; Wang, JT; Weissenstein, U, 2019)	0.51

Excerpt	Reference	Relevance
" This is the first study demonstrating that single oral doses of endoxifen are safe and well tolerated and have sufficient bioavailability to reach systemically effective levels in human subjects."	( Endoxifen, a new cornerstone of breast cancer therapy: demonstration of safety, tolerability, and systemic bioavailability in healthy human subjects. Ahmad, A; Ahmad, I; Kale, P; Krishnappa, M; Rane, RC; Shahabuddin, S; Sheikh, S, 2010)	0.36
" However, direct administration of endoxifen may present the problem of low bioavailability due to its rapid first-pass metabolism via O-glucuronidation."	( Boronic prodrug of endoxifen as an effective hormone therapy for breast cancer. Miele, L; Wang, G; Zhang, C; Zhang, Q; Zheng, S; Zhong, Q, 2015)	0.42
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51
" In phase 1/2 clinical studies, the efficacy of Z-endoxifen, the active isomer of endoxifen, was evaluated in patients with endocrine-refractory metastatic breast cancer as well as in patients with gynecologic, desmoid, and hormone-receptor positive solid tumors, and demonstrated substantial oral bioavailability and promising antitumor activity."	( Endoxifen, an Estrogen Receptor Targeted Therapy: From Bench to Bedside. Goetz, MP; Hawse, JR; Jayaraman, S; Reid, JM, 2021)	0.62
" Weight, race on clearance, and aspartate aminotransferase on the absorption rate constant were identified as significant covariates in the final model."	( Population Pharmacokinetics of Z-Endoxifen in Patients With Advanced Solid Tumors. Adjei, AA; Ames, MM; Buhrow, SA; Covey, JM; Goetz, MP; Koubek, EJ; Larson, TR; McGovern, RM; Ralya, AT; Reid, JM; Takebe, N, 2022)	0.72
" Here, we characterized the pharmacokinetics and oral bioavailability of ENDX in female rats and dogs."	( Bioavailability and Pharmacokinetics of Endoxifen in Female Rats and Dogs: Evidence to Support the Use of Endoxifen to Overcome the Limitations of CYP2D6-Mediated Tamoxifen Metabolism. Ames, MM; Buhrow, SA; Goetz, MP; Jia, L; Koubek, EJ; Reid, JM; Safgren, SL, 2023)	0.91
" A higher bioavailability of tamoxifen in older patients may explain the observed differences."	( Tamoxifen pharmacokinetics and pharmacodynamics in older patients with non-metastatic breast cancer. Gelderblom, H; Guchelaar, HJ; Moes, DJAR; Portielje, JEA; Sanchez-Spitman, A; Souwer, ETD; Swen, JJ; van Gelder, T, 2023)	0.91

Excerpt	Relevance	Reference
"Consistent with previous reports, the dose-response of the E2 effect on the PR expression indicated an ED(50) value of approximately 60 pM and the maximum induction of PR mRNA was nearly ten-fold."	( Endoxifen (4-hydroxy-N-desmethyl-tamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxy-tamoxifen. Desta, Z; Flockhart, DA; Lim, YC; Skaar, TC, 2005)	0.33
" In pre-menopausal breast cancer PM or IM patients, an increase in dosage of tamoxifen or a treatment with LH-RH analogues with aromatase inhibitors (AI) may be beneficial instead of the actual recommendations of a 5-year tamoxifen therapy."	( [CYP2D6 polymorphisms and tamoxifen: therapeutic perspectives in the management of hormonodependent breast cancer patients]. Barrière, J; Ferrero, JM; Formento, JL; Milano, G, 2010)	0.36
" This test could contribute to the personalization and optimization of tamoxifen treatment, but it needs additional validation and simplification before being applicable in future dosing strategies."	( Dextromethorphan as a phenotyping test to predict endoxifen exposure in patients on tamoxifen treatment. Beijnen, JH; de Graan, AJ; de Jongh, FE; de Vos, AI; de Vos, FY; Loos, WJ; Mathijssen, RH; Seynaeve, C; Teunissen, SF; van Alphen, RJ; van der Holt, B; van Schaik, RH; Verweij, J, 2011)	0.37
"We examined the feasibility of using CYP2D6 genotyping to determine optimal tamoxifen dose and investigated whether the key active tamoxifen metabolite, endoxifen, could be increased by genotype-guided tamoxifen dosing in patients with intermediate CYP2D6 metabolism."	( Genotype-guided tamoxifen dosing increases active metabolite exposure in women with reduced CYP2D6 metabolism: a multicenter study. Anderson, SM; Canale, ST; Carey, LA; Chiu, WK; Corso, SW; Dees, EC; Desta, Z; Evans, JP; Flockhart, DA; Friedman, KJ; Graham, ML; Ibrahim, JG; Irvin, WJ; McLeod, HL; Moore, SG; Ogburn, ET; Olajide, OA; Peppercorn, JM; Raab, RE; Walko, CM; Weck, KE, 2011)	0.37
"This study demonstrates the feasibility of genotype-driven tamoxifen dosing and demonstrates that doubling the tamoxifen dose can increase endoxifen concentrations in IM and PM patients."	( Genotype-guided tamoxifen dosing increases active metabolite exposure in women with reduced CYP2D6 metabolism: a multicenter study. Anderson, SM; Canale, ST; Carey, LA; Chiu, WK; Corso, SW; Dees, EC; Desta, Z; Evans, JP; Flockhart, DA; Friedman, KJ; Graham, ML; Ibrahim, JG; Irvin, WJ; McLeod, HL; Moore, SG; Ogburn, ET; Olajide, OA; Peppercorn, JM; Raab, RE; Walko, CM; Weck, KE, 2011)	0.37
" The dosage in patients with endoxifen <40 nmol/l and/or CYP2D6 MPA scores of 0 was increased to 30 mg/day and their metabolite isomers were monitored for up to 90 days."	( Increasing tamoxifen dose in breast cancer patients based on CYP2D6 genotypes and endoxifen levels: effect on active metabolite isomers and the antiestrogenic activity score. Barginear, MF; Desnick, RJ; Jaremko, M; Kasai, Y; Kemeny, M; Peter, I; Raptis, G; Yu, C, 2011)	0.37
"Tamoxifen dosage is based on the one-dose-fits-all approach."	( Tissue distribution of 4-hydroxy-N-desmethyltamoxifen and tamoxifen-N-oxide. Aristarco, V; Decensi, A; Gandini, S; Gjerde, J; Guerrieri-Gonzaga, A; Haugan Moi, LL; Lien, EA; Mellgren, G, 2012)	0.38
" There was wide variability in tamoxifen and metabolite concentrations within the dosing groups."	( Tamoxifen dose and serum concentrations of tamoxifen and six of its metabolites in routine clinical outpatient care. Beijnen, JH; Jager, NG; Linn, SC; Rosing, H; Schellens, JH, 2014)	0.4
" ZB483 was demonstrated to be more efficacious than endoxifen in inhibiting xenograft tumor growth in mice at equal dosage but more so at lower dosage."	( Boronic prodrug of endoxifen as an effective hormone therapy for breast cancer. Miele, L; Wang, G; Zhang, C; Zhang, Q; Zheng, S; Zhong, Q, 2015)	0.42
" These results suggest that fucoidan in the studied form and dosage could be taken concomitantly with letrozole and tamoxifen without the risk of clinically significant interactions."	( The Effect of Undaria pinnatifida Fucoidan on the Pharmacokinetics of Letrozole and Tamoxifen in Patients With Breast Cancer. Fitton, JH; Lowenthal, RM; McGuinness, G; Olesen, I; Oliver, LJ; Patel, R; Peterson, GM; Shastri, M; Tocaciu, S, 2018)	0.48
" Endoxifen steady-state fluctuations within a dosing interval were minimal (<6%)."	( Exploiting Pharmacokinetic Models of Tamoxifen and Endoxifen to Identify Factors Causing Subtherapeutic Concentrations in Breast Cancer Patients. Csajka, C; Joerger, M; Kloft, C; Klopp-Schulze, L; Parra-Guillen, ZP; Ter Heine, R; Wicha, SG, 2018)	0.48
" Our purpose was to develop a prediction model for endoxifen concentrations, as a strategy to individualize tamoxifen treatment by model-informed dosing in order to prevent subtherapeutic exposure (endoxifen < 16 nmol/L) and thus potential failure of therapy."	( Factors affecting inter-individual variability in endoxifen concentrations in patients with breast cancer: results from the prospective TOTAM trial. Abrams, S; Braal, CL; Buijs, SM; Jager, A; Koolen, SLW; Mathijssen, RHJ; Mulder, TAM; van Schaik, RHN; Westenberg, JD, 2022)	0.72
" The remaining unexplained inter-individual variability is still high and therefore model-informed tamoxifen dosing should be accompanied by therapeutic drug monitoring."	( Factors affecting inter-individual variability in endoxifen concentrations in patients with breast cancer: results from the prospective TOTAM trial. Abrams, S; Braal, CL; Buijs, SM; Jager, A; Koolen, SLW; Mathijssen, RHJ; Mulder, TAM; van Schaik, RHN; Westenberg, JD, 2022)	0.72
" Oral dosing of ENDX resulted in substantially higher ENDX concentrations than a similar dose of TAM."	( Bioavailability and Pharmacokinetics of Endoxifen in Female Rats and Dogs: Evidence to Support the Use of Endoxifen to Overcome the Limitations of CYP2D6-Mediated Tamoxifen Metabolism. Ames, MM; Buhrow, SA; Goetz, MP; Jia, L; Koubek, EJ; Reid, JM; Safgren, SL, 2023)	0.91
" Our aim is to develop a population pharmacokinetic (POP-PK) model incorporating a continuous CYP2D6 activity scale to support model informed precision dosing (MIPD) of tamoxifen to determine the optimal tamoxifen starting dose."	( Toward model-informed precision dosing for tamoxifen: A population-pharmacokinetic model with a continuous CYP2D6 activity scale. Agema, BC; Buijs, SM; Jager, A; Koch, BCP; Koolen, SLW; Mathijssen, RHJ; Mürdter, TE; Sassen, SDT; Schwab, M; van Schaik, RHN, 2023)	0.91
" Thereafter, dosing cut-off values for MIPD were determined."	( Toward model-informed precision dosing for tamoxifen: A population-pharmacokinetic model with a continuous CYP2D6 activity scale. Agema, BC; Buijs, SM; Jager, A; Koch, BCP; Koolen, SLW; Mathijssen, RHJ; Mürdter, TE; Sassen, SDT; Schwab, M; van Schaik, RHN, 2023)	0.91
" After external validation and determination of dosing cut-off points, MIPD could reduce the proportion of patients with subtherapeutic endoxifen levels at from 22."	( Toward model-informed precision dosing for tamoxifen: A population-pharmacokinetic model with a continuous CYP2D6 activity scale. Agema, BC; Buijs, SM; Jager, A; Koch, BCP; Koolen, SLW; Mathijssen, RHJ; Mürdter, TE; Sassen, SDT; Schwab, M; van Schaik, RHN, 2023)	0.91

Class	Description
stilbenoid	Any olefinic compound characterised by a 1,2-diphenylethylene backbone.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Tamoxifen Action Pathway	10	27
Tamoxifen Metabolism Pathway	10	27

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Estrogen receptor	Homo sapiens (human)	IC50 (µMol)	0.0300	0.0000	0.7237	32.7000	AID1815022
Aromatase	Homo sapiens (human)	IC50 (µMol)	7.0250	0.0000	1.2904	10.0000	AID1307756; AID1593032; AID1815021; AID751071
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
positive regulation of transcription by RNA polymerase II	Estrogen receptor	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Estrogen receptor	Homo sapiens (human)
antral ovarian follicle growth	Estrogen receptor	Homo sapiens (human)
epithelial cell development	Estrogen receptor	Homo sapiens (human)
chromatin remodeling	Estrogen receptor	Homo sapiens (human)
regulation of DNA-templated transcription	Estrogen receptor	Homo sapiens (human)
signal transduction	Estrogen receptor	Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway	Estrogen receptor	Homo sapiens (human)
positive regulation of cytosolic calcium ion concentration	Estrogen receptor	Homo sapiens (human)
androgen metabolic process	Estrogen receptor	Homo sapiens (human)
male gonad development	Estrogen receptor	Homo sapiens (human)
negative regulation of gene expression	Estrogen receptor	Homo sapiens (human)
positive regulation of phospholipase C activity	Estrogen receptor	Homo sapiens (human)
intracellular steroid hormone receptor signaling pathway	Estrogen receptor	Homo sapiens (human)
intracellular estrogen receptor signaling pathway	Estrogen receptor	Homo sapiens (human)
response to estradiol	Estrogen receptor	Homo sapiens (human)
regulation of toll-like receptor signaling pathway	Estrogen receptor	Homo sapiens (human)
negative regulation of smooth muscle cell apoptotic process	Estrogen receptor	Homo sapiens (human)
negative regulation of canonical NF-kappaB signal transduction	Estrogen receptor	Homo sapiens (human)
negative regulation of DNA-binding transcription factor activity	Estrogen receptor	Homo sapiens (human)
response to estrogen	Estrogen receptor	Homo sapiens (human)
positive regulation of DNA-templated transcription	Estrogen receptor	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Estrogen receptor	Homo sapiens (human)
fibroblast proliferation	Estrogen receptor	Homo sapiens (human)
positive regulation of fibroblast proliferation	Estrogen receptor	Homo sapiens (human)
stem cell differentiation	Estrogen receptor	Homo sapiens (human)
regulation of inflammatory response	Estrogen receptor	Homo sapiens (human)
positive regulation of DNA-binding transcription factor activity	Estrogen receptor	Homo sapiens (human)
RNA polymerase II preinitiation complex assembly	Estrogen receptor	Homo sapiens (human)
uterus development	Estrogen receptor	Homo sapiens (human)
vagina development	Estrogen receptor	Homo sapiens (human)
prostate epithelial cord elongation	Estrogen receptor	Homo sapiens (human)
prostate epithelial cord arborization involved in prostate glandular acinus morphogenesis	Estrogen receptor	Homo sapiens (human)
regulation of branching involved in prostate gland morphogenesis	Estrogen receptor	Homo sapiens (human)
mammary gland branching involved in pregnancy	Estrogen receptor	Homo sapiens (human)
mammary gland alveolus development	Estrogen receptor	Homo sapiens (human)
epithelial cell proliferation involved in mammary gland duct elongation	Estrogen receptor	Homo sapiens (human)
protein localization to chromatin	Estrogen receptor	Homo sapiens (human)
cellular response to estradiol stimulus	Estrogen receptor	Homo sapiens (human)
negative regulation of miRNA transcription	Estrogen receptor	Homo sapiens (human)
regulation of epithelial cell apoptotic process	Estrogen receptor	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Estrogen receptor	Homo sapiens (human)
cellular response to estrogen stimulus	Estrogen receptor	Homo sapiens (human)
negative regulation of chronic inflammatory response	Aromatase	Homo sapiens (human)
steroid biosynthetic process	Aromatase	Homo sapiens (human)
estrogen biosynthetic process	Aromatase	Homo sapiens (human)
androgen catabolic process	Aromatase	Homo sapiens (human)
syncytium formation	Aromatase	Homo sapiens (human)
negative regulation of macrophage chemotaxis	Aromatase	Homo sapiens (human)
sterol metabolic process	Aromatase	Homo sapiens (human)
female genitalia development	Aromatase	Homo sapiens (human)
mammary gland development	Aromatase	Homo sapiens (human)
uterus development	Aromatase	Homo sapiens (human)
prostate gland growth	Aromatase	Homo sapiens (human)
testosterone biosynthetic process	Aromatase	Homo sapiens (human)
positive regulation of estradiol secretion	Aromatase	Homo sapiens (human)
female gonad development	Aromatase	Homo sapiens (human)
response to estradiol	Aromatase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Estrogen receptor	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Estrogen receptor	Homo sapiens (human)
TFIIB-class transcription factor binding	Estrogen receptor	Homo sapiens (human)
transcription coregulator binding	Estrogen receptor	Homo sapiens (human)
transcription corepressor binding	Estrogen receptor	Homo sapiens (human)
transcription coactivator binding	Estrogen receptor	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Estrogen receptor	Homo sapiens (human)
chromatin binding	Estrogen receptor	Homo sapiens (human)
DNA-binding transcription factor activity	Estrogen receptor	Homo sapiens (human)
nuclear receptor activity	Estrogen receptor	Homo sapiens (human)
steroid binding	Estrogen receptor	Homo sapiens (human)
protein binding	Estrogen receptor	Homo sapiens (human)
calmodulin binding	Estrogen receptor	Homo sapiens (human)
beta-catenin binding	Estrogen receptor	Homo sapiens (human)
zinc ion binding	Estrogen receptor	Homo sapiens (human)
TBP-class protein binding	Estrogen receptor	Homo sapiens (human)
enzyme binding	Estrogen receptor	Homo sapiens (human)
protein kinase binding	Estrogen receptor	Homo sapiens (human)
nitric-oxide synthase regulator activity	Estrogen receptor	Homo sapiens (human)
nuclear estrogen receptor activity	Estrogen receptor	Homo sapiens (human)
nuclear estrogen receptor binding	Estrogen receptor	Homo sapiens (human)
estrogen response element binding	Estrogen receptor	Homo sapiens (human)
identical protein binding	Estrogen receptor	Homo sapiens (human)
ATPase binding	Estrogen receptor	Homo sapiens (human)
14-3-3 protein binding	Estrogen receptor	Homo sapiens (human)
sequence-specific double-stranded DNA binding	Estrogen receptor	Homo sapiens (human)
iron ion binding	Aromatase	Homo sapiens (human)
steroid hydroxylase activity	Aromatase	Homo sapiens (human)
electron transfer activity	Aromatase	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Aromatase	Homo sapiens (human)
oxygen binding	Aromatase	Homo sapiens (human)
heme binding	Aromatase	Homo sapiens (human)
aromatase activity	Aromatase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Estrogen receptor	Homo sapiens (human)
nucleoplasm	Estrogen receptor	Homo sapiens (human)
transcription regulator complex	Estrogen receptor	Homo sapiens (human)
cytoplasm	Estrogen receptor	Homo sapiens (human)
Golgi apparatus	Estrogen receptor	Homo sapiens (human)
cytosol	Estrogen receptor	Homo sapiens (human)
plasma membrane	Estrogen receptor	Homo sapiens (human)
membrane	Estrogen receptor	Homo sapiens (human)
chromatin	Estrogen receptor	Homo sapiens (human)
euchromatin	Estrogen receptor	Homo sapiens (human)
protein-containing complex	Estrogen receptor	Homo sapiens (human)
nucleus	Estrogen receptor	Homo sapiens (human)
endoplasmic reticulum	Aromatase	Homo sapiens (human)
endoplasmic reticulum membrane	Aromatase	Homo sapiens (human)
membrane	Aromatase	Homo sapiens (human)
endoplasmic reticulum	Aromatase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (62)

Assay ID	Title	Year	Journal	Article
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1223220	Activity of human MDR1 expressed in pig LLC-PK cells assessed as apparent permeability from apical to basolateral side at 5 uM after 1 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID474292	Inhibition of PKC at 0.025 mM after 90 mins by ELISA	2010	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8	Endoxifen is a new potent inhibitor of PKC: a potential therapeutic agent for bipolar disorder.
AID1152713	Agonist activity at ER in human MCF7:WS8 cells assessed as GREB1 gene expression at 10'-6 M after 48 hrs by RT-PCR analysis	2014	Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11	Influence of the length and positioning of the antiestrogenic side chain of endoxifen and 4-hydroxytamoxifen on gene activation and growth of estrogen receptor positive cancer cells.
AID1223217	Apparent permeability from apical to basolateral side in pig LLC-PK cells at 5 uM after 1 to 4 hrs by LC-MS/MS analysis in presence of LY335979	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID474298	Inhibition of PKC after 90 mins by ELISA	2010	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8	Endoxifen is a new potent inhibitor of PKC: a potential therapeutic agent for bipolar disorder.
AID620856	Binding affinity to bovine serum albumin at pH 7.4 by McGhee and von Hippel method	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID1061857	Binding affinity to ERalpha (unknown origin) relative to tamoxifen	2014	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 24, Issue:1	Design and synthesis of tamoxifen derivatives as a selective estrogen receptor down-regulator.
AID1152712	Agonist activity at ER in human MCF7:WS8 cells assessed as pS2 gene expression at 10'-6 M after 48 hrs by RT-PCR analysis	2014	Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11	Influence of the length and positioning of the antiestrogenic side chain of endoxifen and 4-hydroxytamoxifen on gene activation and growth of estrogen receptor positive cancer cells.
AID620855	Binding affinity to bovine serum albumin at pH 7.4 by Stern-Volmer plot	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID620848	Effect on secondary structure of bovine serum albumin assessed as alpha-helix content at 0.5 uM at pH 7.4 by circular dichroism method (Rvb = 63 %)	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID1223216	Efflux ratio of apparent permeability from basolateral to apical to apical to basolateral side in pig LLC-PK cells at 5 uM after 1 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1152716	Effect on ER-alpha protein level in human MCF7:WS8 cells after 24 hrs by Western blot analysis relative to control	2014	Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11	Influence of the length and positioning of the antiestrogenic side chain of endoxifen and 4-hydroxytamoxifen on gene activation and growth of estrogen receptor positive cancer cells.
AID620852	Effect on secondary structure of bovine serum albumin assessed as beta-sheet content at 0.5 uM at pH 7.4 by circular dichroism method (Rvb = 16 %)	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID1815023	Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by cell counter method	2021	European journal of medicinal chemistry, Nov-15, Volume: 224	Balanced dual acting compounds targeting aromatase and estrogen receptor α as an emerging therapeutic opportunity to counteract estrogen responsive breast cancer.
AID474296	Toxicity in rat at 4 mg/kg, po after 28 days	2010	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8	Endoxifen is a new potent inhibitor of PKC: a potential therapeutic agent for bipolar disorder.
AID1223221	Activity of human MDR1 expressed in pig LLC-PK cells assessed as apparent permeability from basolateral to apical side at 5 uM after 1 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1480300	Selectivity index, ratio of cytotoxic activity for human HeLa cells to IC50 for Ebolavirus glycoprotein/matrix protein VP40 entry in human HeLa cells	2018	Journal of medicinal chemistry, 04-26, Volume: 61, Issue:8	Computer-Aided Discovery and Characterization of Novel Ebola Virus Inhibitors.
AID1223231	Drug uptake in MDR1A-deficient CF-1 mouse brain at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1480299	Selectivity index, ratio of cytotoxic activity for HEK293 cells to IC50 for Ebolavirus glycoprotein/matrix protein VP40 entry in human HeLa cells	2018	Journal of medicinal chemistry, 04-26, Volume: 61, Issue:8	Computer-Aided Discovery and Characterization of Novel Ebola Virus Inhibitors.
AID1307756	Inhibition of human placental microsomal aromatase using testosterone as substrate assessed as formation of estradiol after 10 mins	2016	Journal of medicinal chemistry, 06-09, Volume: 59, Issue:11	Recent Progress in the Discovery of Next Generation Inhibitors of Aromatase from the Structure-Function Perspective.
AID1322008	Antiestrogenic activity in human MCF7 cells assessed as beta-estradiol-induced progesterone receptor mRNA expression at 1 uM after 24 hrs by RT-PCR assay relative to beta-estradiol	2016	Bioorganic & medicinal chemistry, 11-01, Volume: 24, Issue:21	A new Suzuki synthesis of triphenylethylenes that inhibit aromatase and bind to estrogen receptors α and β.
AID1223233	Drug uptake in MDR1A-deficient CF-1 mouse brain at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis relative to wild-type	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1061856	Upregulation of ERalpha protein levels in human MCF7 cells at 10 uM after 6 hrs by Western blot method	2014	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 24, Issue:1	Design and synthesis of tamoxifen derivatives as a selective estrogen receptor down-regulator.
AID1152714	Agonist activity at ER in human MCF7:WS8 cells assessed as increase in PgR gene expression at 10'-6 M after 48 hrs by RT-PCR analysis relative to control	2014	Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11	Influence of the length and positioning of the antiestrogenic side chain of endoxifen and 4-hydroxytamoxifen on gene activation and growth of estrogen receptor positive cancer cells.
AID1223228	Drug uptake in wild-type CF-1 mouse liver at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1593034	Inhibition of recombinant human aromatase at 200 uM preincubated for 10 mins followed by substrate and beta-NADP+ addition and measured for 60 mins by fluorescence method	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Rational design of allosteric modulators of the aromatase enzyme: An unprecedented therapeutic strategy to fight breast cancer.
AID1223225	Activity of human MDR1 expressed in pig LLC-PK cells assessed as efflux ratio of apparent permeability from basolateral to apical to apical to basolateral side at 5 uM after 1 to 4 hrs by LC-MS/MS analysis in presence of LY335979	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID620854	Effect on secondary structure of bovine serum albumin assessed as random coil content at 0.5 uM at pH 7.4 by circular dichroism method (Rvb = 6 %)	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID1223230	Drug uptake in wild-type CF-1 mouse brain at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID474293	Inhibition of PKC at 0.2 mM after 90 mins by ELISA	2010	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8	Endoxifen is a new potent inhibitor of PKC: a potential therapeutic agent for bipolar disorder.
AID1815022	Binding affinity to human ERalpha measured after 2 hrs by fluorescence polarization plate reader	2021	European journal of medicinal chemistry, Nov-15, Volume: 224	Balanced dual acting compounds targeting aromatase and estrogen receptor α as an emerging therapeutic opportunity to counteract estrogen responsive breast cancer.
AID620851	Effect on secondary structure of bovine serum albumin assessed as beta antiparallel content at 0.5 uM at pH 7.4 by circular dichroism method (Rvb = 3 %)	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID1223224	Activity of human MDR1 expressed in pig LLC-PK cells assessed as apparent permeability from basolateral to apical side at 5 uM after 1 to 4 hrs by LC-MS/MS analysis in presence of LY335979	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1152696	Agonist activity at ER in human MCF7:WS8 cells assessed as cell growth by measuring DNA level at 10'-12 to 10'-6 M after 7 days by fluorescence analysis	2014	Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11	Influence of the length and positioning of the antiestrogenic side chain of endoxifen and 4-hydroxytamoxifen on gene activation and growth of estrogen receptor positive cancer cells.
AID1223227	Drug uptake in MDR1A-deficient CF-1 mouse plasma at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1223226	Drug uptake in wild-type CF-1 mouse plasma at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1230131	Reduction in endogenous ERalpha expression in human MCF7 cells at 10 uM after 6 hrs by Western blot analysis	2015	Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13	Synthesis and evaluation of tamoxifen derivatives with a long alkyl side chain as selective estrogen receptor down-regulators.
AID1815024	Antiproliferative activity against human MCF-10A cells assessed as reduction in cell viability after 72 hrs by cell counter method	2021	European journal of medicinal chemistry, Nov-15, Volume: 224	Balanced dual acting compounds targeting aromatase and estrogen receptor α as an emerging therapeutic opportunity to counteract estrogen responsive breast cancer.
AID1593033	Inhibition of recombinant human aromatase at 100 uM preincubated for 10 mins followed by substrate and beta-NADP+ addition and measured for 60 mins by fluorescence method	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Rational design of allosteric modulators of the aromatase enzyme: An unprecedented therapeutic strategy to fight breast cancer.
AID1223219	Efflux ratio of apparent permeability from basolateral to apical to apical to basolateral side in pig LLC-PK cells at 5 uM after 1 to 4 hrs by LC-MS/MS analysis in presence of LY335979	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1223223	Activity of human MDR1 expressed in pig LLC-PK cells assessed as apparent permeability from apical to basolateral side at 5 uM after 1 to 4 hrs by LC-MS/MS analysis in presence of LY335979	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1223214	Apparent permeability from apical to basolateral side in pig LLC-PK cells at 5 uM after 1 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID620853	Effect on secondary structure of bovine serum albumin assessed as turn structure content at 0.5 uM at pH 7.4 by circular dichroism method (Rvb = 12 %)	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID1480298	Inhibition of Ebolavirus glycoprotein/matrix protein VP40 entry in human HeLa cells after 4.5 hrs beta-lactamase reporter assay	2018	Journal of medicinal chemistry, 04-26, Volume: 61, Issue:8	Computer-Aided Discovery and Characterization of Novel Ebola Virus Inhibitors.
AID473403	Antiestrogenic activity in human ERalpha expressing MCF7:WS8 cells assessed as inhibition of estradiol-induced proliferation at 1 uM after 7 days	2010	Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8	Structure-function relationships of estrogenic triphenylethylenes related to endoxifen and 4-hydroxytamoxifen.
AID473402	Estrogenic activity in human ERalpha expressing MCF7:WS8 cells assessed as stimulation of cell proliferation after 7 days	2010	Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8	Structure-function relationships of estrogenic triphenylethylenes related to endoxifen and 4-hydroxytamoxifen.
AID1223232	Ratio of drug level in brain to plasma in MDR1A-deficient CF-1 mouse at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1815021	Inhibition of human aromatase assessed as reduction in fluorescence intensity preincubated with NADPH regenerating system for 10 mins followed by substrate addition incubated for 60 mins by fluorescence based microplate reader analysis	2021	European journal of medicinal chemistry, Nov-15, Volume: 224	Balanced dual acting compounds targeting aromatase and estrogen receptor α as an emerging therapeutic opportunity to counteract estrogen responsive breast cancer.
AID474297	Toxicity in mouse at 8 mg/kg, po after 28 days	2010	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8	Endoxifen is a new potent inhibitor of PKC: a potential therapeutic agent for bipolar disorder.
AID1223218	Apparent permeability from basolateral to apical side in pig LLC-PK cells at 5 uM after 1 to 4 hrs by LC-MS/MS analysis in presence of LY335979	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID620850	Binding affinity to bovine serum albumin at pH 7.4 by fluorescence spectroscopy	2011	European journal of medicinal chemistry, Sep, Volume: 46, Issue:9	Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
AID1815025	Antagonist activity at ERalpha (unknown origin) expressed in human MCF7 cells assessed as reduction in PGR gene expression at 1 uM for 24 hrs by real time qPCR analysis	2021	European journal of medicinal chemistry, Nov-15, Volume: 224	Balanced dual acting compounds targeting aromatase and estrogen receptor α as an emerging therapeutic opportunity to counteract estrogen responsive breast cancer.
AID1223229	Drug uptake in MDR1A-deficient CF-1 mouse liver at 5 mg/kg, po after 0.5 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1223222	Activity of human MDR1 expressed in pig LLC-PK cells assessed as efflux ratio of apparent permeability from basolateral to apical to apical to basolateral side at 5 uM after 1 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID751071	Inhibition of human recombinant placental aromatase	2013	Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11	Synthesis of mixed (E,Z)-, (E)-, and (Z)-norendoxifen with dual aromatase inhibitory and estrogen receptor modulatory activities.
AID1223215	Apparent permeability from basolateral to apical side in pig LLC-PK cells at 5 uM after 1 to 4 hrs by LC-MS/MS analysis	2011	Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 39, Issue:3	Endoxifen, the active metabolite of tamoxifen, is a substrate of the efflux transporter P-glycoprotein (multidrug resistance 1).
AID1593032	Inhibition of recombinant human aromatase preincubated for 10 mins followed by substrate and beta-NADP+ addition and measured for 60 mins by fluorescence method	2019	European journal of medicinal chemistry, Apr-15, Volume: 168	Rational design of allosteric modulators of the aromatase enzyme: An unprecedented therapeutic strategy to fight breast cancer.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (0.94)	18.7374
1990's	1 (0.47)	18.2507
2000's	18 (8.45)	29.6817
2010's	149 (69.95)	24.3611
2020's	43 (20.19)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	18 (8.37%)	5.53%
Reviews	16 (7.44%)	6.00%
Case Studies	5 (2.33%)	4.05%
Observational	3 (1.40%)	0.25%
Other	173 (80.47%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	3.99	1	1	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.1	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
phenytoin [no description available]	2.1	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	3.23	1	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
anastrozole [no description available]	3.66	2	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
aprindine Aprindine: A class Ib anti-arrhythmia agent used to manage ventricular and supraventricular arrhythmias.	2.17	1	0	indanes
cogentin [no description available]	2.17	1	0	diarylmethane
bicalutamide bicalutamide: approved for treatment of advanced prostate cancer. N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide : A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group.. bicalutamide : A racemate comprising of equal amounts of (R)-bicalutamide and (S)-bicalutamide. It is an oral non-steroidal antiandrogen used in the treatment of prostate cancer and hirsutism.	2.21	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.	2.05	1	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
cyclofenil Cyclofenil: A gonadal stimulant and inducer of ovulation. It is used in the treatment of infertility and amenorrhea, but is thought to be less effective than CLOMIPHENE.	2.15	1	0	organic molecular entity
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	3.5	1	1	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
ebastine [no description available]	2.17	1	0	organic molecular entity
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.06	1	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
letrozole [no description available]	3.3	5	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.1	1	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.1	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.06	1	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
vincristine [no description available]	2.17	1	0	acetate ester; formamides; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
triphenylethylene [no description available]	2.17	1	0	stilbenoid
rhodamine b rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.	2.08	1	0	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	3.58	2	0	cyclohexanols; secondary alcohol	solvent
pregnenolone [no description available]	2.1	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	2.08	1	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	3.64	1	1	catechin	antioxidant; plant metabolite
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.54	2	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	2.51	2	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
thioproperazine thioproperazine: was heading 1963-94; use PHENOTHIAZINES to search THIOPROPERAZINE 1966-94. thioproperazine : A phenothiazine derivative in which the phenothiazine tricycle has a dimethylaminosulfonyl substituent at the 2-position and a 3-(4-methylpiperazin-1-yl)propyl group at N-10.	2.17	1	0	N-alkylpiperazine; N-methylpiperazine; phenothiazines; sulfonamide	phenothiazine antipsychotic drug
cepharanthine cepharanthine: isoquinoline alkaloid from tubers of STEPHANIA; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. cepharanthine : A bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.	2.17	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
formestane [no description available]	3.23	1	0	17-oxo steroid; 3-oxo-Delta(4) steroid; enol; hydroxy steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	2.08	1	0	cycloalkene; p-menthadiene	human metabolite
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.51	2	0	elemental platinum; nickel group element atom; platinum group metal atom
clemastine Clemastine: A histamine H1 antagonist used as the hydrogen fumarate in hay fever, rhinitis, allergic skin conditions, and pruritus. It causes drowsiness.. clemastine : 2-[(2R)-1-Methylpyrrolidin-2-yl]ethanol in which the hydrogen of the hydroxy group is substituted by a 1-(4-chlorophenyl)-1-phenylethyl group (R configuration). An antihistamine with antimuscarinic and moderate sedative properties, it is used as its fumarate salt for the symptomatic relief of allergic conditions such as rhinitis, urticaria, conjunctivitis and in pruritic (severe itching) skin conditions.	2.17	1	0	monochlorobenzenes; N-alkylpyrrolidine	anti-allergic agent; antipruritic drug; H1-receptor antagonist; muscarinic antagonist
alkenes [no description available]	2.17	1	0
sq-11725 Nadolol: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for MIGRAINE DISORDERS and for tremor.. nadolol : Nadolol is a diastereoisomeric mixture consisting of equimolar amounts of the four possible 2,3-cis-isomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol.	2.21	1	0
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.06	1	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	2.13	1	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
raloxifene hydrochloride Raloxifene Hydrochloride: A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.. raloxifene hydrochloride : A hydrochloride salt resulting from the reaction of equimolar amounts of raloxifene and hydrogen chloride.	2.11	1	0	hydrochloride	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
fadrozole Fadrozole: A selective aromatase inhibitor effective in the treatment of estrogen-dependent disease including breast cancer.	3.23	1	0	imidazopyridine
aromasil [no description available]	2.21	1	0	17-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor; environmental contaminant; xenobiotic
mibefradil Mibefradil: A benzimidazoyl-substituted tetraline that selectively binds and inhibits CALCIUM CHANNELS, T-TYPE.	2.17	1	0	tetralins	T-type calcium channel blocker
venlafaxine hydrochloride Venlafaxine Hydrochloride: A cyclohexanol and phenylethylamine derivative that functions as a SEROTONIN AND NORADRENALINE REUPTAKE INHIBITOR (SNRI) and is used as an ANTIDEPRESSIVE AGENT.	3.14	1	0	hydrochloride
1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene: structure given in first source	3	4	0
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol [no description available]	3.48	7	0	stilbenoid
16-fluoroestradiol 16-fluoroestradiol: RN refers to (16beta,17beta)-isomer	3.53	1	1
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.17	1	0	1,2,3-triazole
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2.1	1	0	anthocyanidin chloride
tetrandrine tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity	2.17	1	0	bisbenzylisoquinoline alkaloid; isoquinolines
combretastatin combretastatin: cytotoxic principle from South African tree COMBRETUM caffrum; structure given in first source; acts at COLCHICINE site of TUBULIN	2.15	1	0
fulvestrant Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.	5.35	4	1	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
gefitinib [no description available]	2.17	1	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
abiraterone [no description available]	2.21	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; pyridines	antineoplastic agent; EC 1.14.99.9 (steroid 17alpha-monooxygenase) inhibitor
bazedoxifene [no description available]	2.17	1	0	phenylindole
dibenzheptropine dibenzheptropine: minor descriptor (65-85); on-line & Index Medicus search TROPANES (66-85); RN given refers to parent cpd. deptropine : An azabicycloalkane that is the 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl ether of tropine.	2.17	1	0	organic tricyclic compound
dronedarone Dronedarone: A non-iodinated derivative of amiodarone that is used for the treatment of ARRHYTHMIA.. dronedarone : A member of the class of 1-benzofurans used for the treatment of cardiac arrhythmias.	2.17	1	0	1-benzofurans; aromatic ether; aromatic ketone; sulfonamide; tertiary amino compound	anti-arrhythmia drug; environmental contaminant; xenobiotic
lapatinib [no description available]	2.15	1	0	furans; organochlorine compound; organofluorine compound; quinazolines	antineoplastic agent; tyrosine kinase inhibitor
sr 142806 [no description available]	2.17	1	0
vincaleukoblastine [no description available]	2.17	1	0	acetate ester; indole alkaloid fundamental parent; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; immunosuppressive agent; microtubule-destabilising agent; plant metabolite
gant 61 GANT 61: a sonic hedgehog pathway inhibitor and Gli inhibitor; structure in first source. GANT61 : An aminal that is hexahydropyrimidine which is substituted on each nitrogen by a 2-(dimethylamino)benzyl group, and at the aminal carbon by a pyridin-4-yl group. A Hedgehog signaling pathway and Gli protein inhibitor.	2.17	1	0	aminal; dialkylarylamine; pyridines; substituted aniline; tertiary amino compound	antineoplastic agent; apoptosis inducer; glioma-associated oncogene inhibitor; Hedgehog signaling pathway inhibitor
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.21	1	0	taxifolin	metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.49	2	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	3.43	1	1	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
afimoxifene afimoxifene : A tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen.	10.67	53	2	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.17	1	0	stilbene
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	2.41	1	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	2.17	1	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.06	1	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
tamoxifen [no description available]	17.58	207	18	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
toremifene Toremifene: A first generation selective estrogen receptor modulator (SERM). Like TAMOXIFEN, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue.	2.75	3	0	aromatic ether; organochlorine compound; tertiary amine	antineoplastic agent; bone density conservation agent; estrogen antagonist; estrogen receptor modulator
tamoxifen n-oxide tamoxifen N-oxide : A tertiary amine oxide resulting from the formal oxidation of the amino group of tamoxifen.	3.01	4	0	aromatic ether; tertiary amine oxide	anti-estrogen; metabolite
1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene: structure given in first source	2.17	1	0	stilbenoid
ly335979 [no description available]	2.47	2	0	carbopolycyclic compound
am 630 iodopravadoline: an aminoalkylindole; a competitive cannabinoid receptor antagonist; structure given in first source	2.13	1	0	N-acylindole
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940	2.13	1	0	alkylbenzene; ring assembly
mangostin mangostin: xanthone from rind of Garcinia mangostana Linn. fruit. alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.	2.08	1	0	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite
fenretinide Fenretinide: A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.. 4-hydroxyphenyl retinamide : A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.	3.43	1	1	monocarboxylic acid amide; retinoid	antineoplastic agent; antioxidant
vinorelbine [no description available]	2.17	1	0	acetate ester; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; ring assembly; vinca alkaloid	antineoplastic agent; photosensitizing agent
bosutinib 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-3-quinolinecarbonitrile: a Src kinase inhibitor; structure in first source	2.17	1	0	aminoquinoline; aromatic ether; dichlorobenzene; N-methylpiperazine; nitrile; tertiary amino compound	antineoplastic agent; tyrosine kinase inhibitor
afimoxifene [no description available]	2.05	1	0
dextromethorphan Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.	5.78	7	1	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
dextrorphan Dextrorphan: Dextro form of levorphanol. It acts as a noncompetitive NMDA receptor antagonist, among other effects, and has been proposed as a neuroprotective agent. It is also a metabolite of DEXTROMETHORPHAN.	2.99	1	0	morphinane alkaloid
n-desmethyltamoxifen N-desmethyltamoxifen: main metabolite of tamoxifen; RN given refers to (Z)-isomer	5.49	22	0	stilbenoid
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	2.1	1	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
telapristone acetate telapristone acetate: structure in first source	3.5	1	1	steroid ester
adw 742 [no description available]	2.17	1	0
rucaparib AG14447: Poly(ADP-ribose) polymerase inhibitor; structure in first source	2.13	1	0	azepinoindole; caprolactams; organofluorine compound; secondary amino compound	antineoplastic agent; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
cediranib [no description available]	2.17	1	0	aromatic ether
u 18666a 3-beta-(2-(diethylamino)ethoxy)androst-5-en-17-one: inhibits cycloartenol synthase. 3beta-(2-diethylaminoethoxy)androst-5-en-17-one hydrochloride : A hydrochloride obtained by reaction of 3beta-(2-diethylaminoethoxy)androst-5-en-17-one with one equivalent of hydrochloric acid. It is a cholesterol synthesis and transport inhibitor.	2.17	1	0	hydrochloride	antiviral agent; EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor; Hedgehog signaling pathway inhibitor; nicotinic antagonist; sterol biosynthesis inhibitor
vindesine [no description available]	2.17	1	0
mdv 3100 [no description available]	2.21	1	0	(trifluoromethyl)benzenes; benzamides; imidazolidinone; monofluorobenzenes; nitrile; thiocarbonyl compound	androgen antagonist; antineoplastic agent
chitosan [no description available]	2.49	2	0
bix 01294 [no description available]	2.17	1	0	piperidines
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	2.13	1	0	nucleoside triphosphate analogue
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.13	1	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor

Condition	Indicated	Relationship Strength	Studies	Trials
Breast Cancer [description not available]	0	17.48	163	17
Breast Neoplasms Tumors or cancer of the human BREAST.	1	19.48	163	17
Congenital Zika Syndrome [description not available]	0	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	0	2.91	3	0
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	0	2.25	1	0
Hypomania [description not available]	0	4.42	3	1
Affective Psychosis, Bipolar [description not available]	0	4.64	4	1
Bipolar Disorder A major affective disorder marked by severe mood swings (manic or major depressive episodes) and a tendency to remission and recurrence.	1	6.64	4	1
Benign Neoplasms [description not available]	0	2.9	2	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	1	4.9	2	0
Adverse Drug Event [description not available]	0	3.46	2	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	0	3.46	2	0
Local Neoplasm Recurrence [description not available]	0	7.9	9	1
Invasiveness, Neoplasm [description not available]	0	2.25	1	0
Genetic Predisposition [description not available]	0	3.23	1	0
Joint Pain [description not available]	0	3.23	1	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	0	3.23	1	0
Arthralgia Pain in the joint.	0	3.23	1	0
Hot Flashes A sudden, temporary sensation of heat predominantly experienced by some women during MENOPAUSE. (Random House Unabridged Dictionary, 2d ed)	0	4.78	6	0
Metastase [description not available]	0	7.22	4	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	0	7.22	4	1
Age-Related Osteoporosis [description not available]	0	2.15	1	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	0	2.15	1	0
B16 Melanoma [description not available]	0	2.17	1	0
Recrudescence [description not available]	0	2.77	3	0
Disease Exacerbation [description not available]	0	3.12	1	0
Experimental Mammary Neoplasms [description not available]	0	2.08	1	0
Malignant Melanoma [description not available]	0	3.71	3	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	0	3.71	3	0
Carcinoma, Anaplastic [description not available]	0	3	1	0
Hormone-Dependent Neoplasms [description not available]	0	3.67	3	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	0	3	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	0	2.1	1	0
Aura [description not available]	0	2.1	1	0
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	0	2.1	1	0
Adenocarcinoma, Basal Cell [description not available]	0	2.1	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	0	2.1	1	0
Cancer of Skin [description not available]	0	3.03	1	0
Skin Neoplasms Tumors or cancer of the SKIN.	0	3.03	1	0
Atypical Ductal Hyperplasia [description not available]	0	5.64	3	2
Carcinoma, Intraductal, Noninfiltrating A noninvasive (noninfiltrating) carcinoma of the breast characterized by a proliferation of malignant epithelial cells confined to the mammary ducts or lobules, without light-microscopy evidence of invasion through the basement membrane into the surrounding stroma.	1	7.64	3	2
Benign Neoplasms, Brain [description not available]	0	2.13	1	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	0	2.13	1	0
Carcinoma, Ductal, Breast An invasive (infiltrating) CARCINOMA of the mammary ductal system (MAMMARY GLANDS) in the human BREAST.	0	3.86	2	0
Breast Pain [description not available]	0	3.04	1	0
Mastodynia Pain in the breast generally classified as cyclical (associated with menstrual periods), or noncyclical, i.e. originating from the breast or nearby muscles or joints, ranging from minor discomfort to severely incapacitating.	0	3.04	1	0
Colitis Gravis [description not available]	0	2.13	1	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	0	2.13	1	0
Breast Cancer, Male [description not available]	0	3.53	1	1
Female Genital Neoplasms [description not available]	0	3.53	1	1
Genital Neoplasms, Female Tumor or cancer of the female reproductive tract (GENITALIA, FEMALE).	0	3.53	1	1
Breast Neoplasms, Male Any neoplasms of the male breast. These occur infrequently in males in developed countries, the incidence being about 1% of that in females.	0	3.53	1	1
Depression, Involutional Form of depression in those MIDDLE AGE with feelings of ANXIETY.	0	2.96	1	0
Depressive Disorder, Major Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)	0	2.96	1	0
Carcinoma, Lobular A type of BREAST CANCER where the abnormal malignant cells form in the lobules, or milk-producing glands, of the breast.	0	3.43	1	1
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	0	2.05	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	0	2.05	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	0	2.08	1	0
Cancer of Liver [description not available]	0	1.99	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	0	1.99	1	0
Chylopericardium [description not available]	0	1.97	1	0
Pericardial Effusion Fluid accumulation within the PERICARDIUM. Serous effusions are associated with pericardial diseases. Hemopericardium is associated with trauma. Lipid-containing effusion (chylopericardium) results from leakage of THORACIC DUCT. Severe cases can lead to CARDIAC TAMPONADE.	0	1.97	1	0
Pleural Effusion Presence of fluid in the pleural cavity resulting from excessive transudation or exudation from the pleural surfaces. It is a sign of disease and not a diagnosis in itself.	0	1.97	1	0

4-hydroxy-n-desmethyltamoxifen

Description

Cross-References

Synonyms (63)

Research Excerpts

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (1)

Pathways (2)

Protein Targets (2)

Inhibition Measurements

Biological Processes (55)

Molecular Functions (33)

Ceullar Components (13)

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Research

Studies (213)

Study Types

4-hydroxy-n-desmethyltamoxifen

Description

Cross-References

Synonyms (63)

Research Excerpts

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (1)

Pathways (2)

Protein Targets (2)

Inhibition Measurements

Biological Processes (55)

Molecular Functions (33)

Ceullar Components (13)

Bioassays (62)

Research

Studies (213)

Study Types

Related Drugs (93)

Related Conditions (63)