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Atlas / Drug / Tamoxifen

Tamoxifen

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Also known as ICI-47699MammatonNovaldexNSC-727681TamoplexTamoxifeneTamoxifenoTomoxifenSID11113844SID26752017SID26752018SID56320712SID90340643SID50104683SID50104684SID50104685SID50104686(Z)-TamoxifenSID144210857

Summary

Tamoxifen (CHEMBL83) is an approved small-molecule antineoplastic agent (ATC L02BA01) targeting GPER1, ESR1, and ESR2; indicated across 41 conditions including neoplasm and breast carcinoma.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: L02BA01
  • Targets: 3 (GPER1, ESR1, ESR2)
  • Indications: 41 conditions
  • Clinical trials: 246
  • Chemistry: 371.5 Da · C26H29NO

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL83
NameTamoxifen
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID2733526
ChEBICHEBI:41774
ATCL02BA01
Molecular formulaC26H29NO
Molecular weight371.5
InChIKeyNKANXQFJJICGDU-QPLCGJKRSA-N

SMILES: CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3

IUPAC name: 2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine

Pharmacological roles (ChEBI): antineoplastic agent, estrogen receptor antagonist, bone density conservation agent, estrogen receptor modulator, estrogen antagonist, angiogenesis inhibitor, EC 2.7.11.13 (protein kinase C) inhibitor, EC 1.2.3.1 (aldehyde oxidase) inhibitor.

Also known as: ICI-47699, Mammaton, Novaldex, NSC-727681, Tamoplex, Tamoxifen, Tamoxifene, Tamoxifeno, tamoxifene, tamoxifen, Tomoxifen, SID11113844

Parent form; salt/anhydrous children: CHEMBL786

Patent coverage: 44,273 distinct patent families (171,635 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
GPER1GPERFull agonist60.2%Q99527
ESR1Estrogen receptor-αAgonist7.821.7%P03372
ESR2Estrogen receptor-βAgonist7.160.2%Q92731
Maxi Cl-
VRAC

Broader ChEMBL bioactivity targets: 87 (assay-derived). Sample: Microtubule-associated protein tau, Streptokinase A, Nuclear receptor ROR-gamma, 4’-phosphopantetheinyl transferase ffp, Ferritin light chain, NPC intracellular cholesterol transporter 1, Ras-related protein Rab-9A, Muscarinic acetylcholine receptor M4, Receptor tyrosine-protein kinase erbB-2, 5-hydroxytryptamine receptor 2B.

Bioactivity

ChEMBL activities: 157 potent at pChembl ≥ 5 of 234 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
ESR29.29Ki0.51nMCHEMBL_ACT_10939218
EBP9Kd1nMCHEMBL_ACT_1193852
ESR18.82IC501.5nMCHEMBL_ACT_19249437
EBPL8.55Ki2.8nMCHEMBL_ACT_12633686
EBP8.3Ki5nMCHEMBL_ACT_1483849
ESR18.1IC508nMCHEMBL_ACT_16505356
ESR18.08IC508.4nMCHEMBL_ACT_796232
SIGMAR18.06Ki8.71nMCHEMBL_ACT_7803903
ESR17.92Ki11.9nMCHEMBL_ACT_1300351
EBP7.92IC5012nMCHEMBL_ACT_216040
SIGMAR17.68IC5021nMCHEMBL_ACT_7803902
ESR17.61IC5024.55nMCHEMBL_ACT_15740574
ESR17.51Ki31.19nMCHEMBL_ACT_3397768
ESR17.46Ki34.4nMCHEMBL_ACT_1300353
SIGMAR17.46Ki35nMCHEMBL_ACT_1483850
ESR17.41IC5039nMCHEMBL_ACT_13373750
ESR17.38IC5042nMCHEMBL_ACT_1196237
ESR17.24IC5058nMCHEMBL_ACT_23232649
ESR17.21IC5060.9nMCHEMBL_ACT_15116745
ESR17.21IC5061nMCHEMBL_ACT_15116772
ESRRG7.21IC5062.2nMCHEMBL_ACT_18217550
ESR17.21IC5060.9nMCHEMBL_ACT_18565872
ESR17.21IC5060.9nMCHEMBL_ACT_20702776
ESR17.16IC5070nMCHEMBL_ACT_18565761
ESR17.16IC5070nMCHEMBL_ACT_20702731
ESR17.16IC5070nMCHEMBL_ACT_2399275
ESR17.16IC5069nMCHEMBL_ACT_24506367
ESR27.1IC5079.7nMCHEMBL_ACT_18217541
ESR17.04AC5090.3nMCHEMBL_ACT_25167271
ABCB17Ki100nMCHEMBL_ACT_1276443

Target pathways

Aggregated over 3 target gene(s): GPER1, ESR1, ESR2.

Top Reactome pathways

20 total, by targets touching each:

PathwayTargetsGenes
PIP3 activates AKT signaling2ESR1, ESR2
Constitutive Signaling by Aberrant PI3K in Cancer2ESR1, ESR2
Nuclear Receptor transcription pathway2ESR1, ESR2
PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling2ESR1, ESR2
ESR-mediated signaling2ESR1, ESR2
Extra-nuclear estrogen signaling2ESR1, ESR2
Nuclear signaling by ERBB41ESR1
Peptide ligand-binding receptors1GPER1
SUMOylation of intracellular receptors1ESR1
G alpha (i) signalling events1GPER1
Ovarian tumor domain proteases1ESR1
TFAP2 (AP-2) family regulates transcription of growth factors and their receptors1ESR1
RUNX1 regulates estrogen receptor mediated transcription1ESR1
RUNX1 regulates transcription of genes involved in WNT signaling1ESR1
Regulation of RUNX2 expression and activity1ESR1
Estrogen-dependent gene expression1ESR1
GPER1 signaling1GPER1
Mitochondrial unfolded protein response (UPRmt)1ESR1
Developmental Lineage of Mammary Gland Luminal Epithelial Cells1ESR1
Developmental Lineage of Mammary Gland Alveolar Cells1ESR1

Dominant GO biological processes

GO termTargets
positive regulation of transcription by RNA polymerase II3
cellular response to estradiol stimulus3
signal transduction3
positive regulation of cytosolic calcium ion concentration2
negative regulation of gene expression2
nuclear receptor-mediated steroid hormone signaling pathway2
steroid hormone receptor signaling pathway2
negative regulation of transcription by RNA polymerase II2
regulation of DNA-templated transcription2
regulation of transcription by RNA polymerase II2
estrogen receptor signaling pathway2
positive regulation of DNA-templated transcription2
obsolete positive regulation of DNA-binding transcription factor activity2
cellular response to oxygen-containing compound2
positive regulation of protein phosphorylation1

Indications & clinical

Indications

41 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
neoplasm4MONDO:0005070EFO:0000616
breast carcinoma3MONDO:0004989EFO:0000305
breast neoplasm3MONDO:0021100MONDO:0007254
ductal breast carcinoma in situ3MONDO:0005023EFO:0000432
hyperplasia3MONDO:0005043EFO:0000536
hypertensive disorder3MONDO:0005044EFO:0000537
infertility disorder3MONDO:0005047EFO:0000545
ovarian carcinoma3MONDO:0005140EFO:0001075
coronary artery disorder3MONDO:0005010EFO:0001645
male breast carcinoma3MONDO:0005628EFO:0006861
fallopian tube carcinoma3MONDO:0006206EFO:1000251
myocardial ischemia3MONDO:0024644EFO:1001375
peritoneal neoplasm3MONDO:0006901MONDO:0002087
ovarian cancer3MONDO:0008170MONDO:0008170
Duchenne muscular dystrophy3MONDO:0010679MONDO:0010679
adenoma2MONDO:0004972EFO:0000232
urinary bladder neoplasm2MONDO:0004987EFO:0000294
diffuse large B-cell lymphoma2MONDO:0018905EFO:0000403
glioblastoma2MONDO:0018177EFO:0000519
HIV infectious disease2MONDO:0005109EFO:0000764
cervical adenocarcinoma2MONDO:0005153EFO:0001416
male infertility2MONDO:0005372EFO:0004248
neuroendocrine neoplasm2MONDO:0019496EFO:1001901
gynecomastia disorder2MONDO:0001571HP:0000771
amyotrophic lateral sclerosis2MONDO:0004976MONDO:0004976
bipolar disorder2MONDO:0004985MONDO:0004985
endometrium neoplasm2MONDO:0021251MONDO:0011962
IgG4-related retroperitoneal fibrosis2MONDO:0018848MONDO:0018848
hereditary hemorrhagic telangiectasia2MONDO:0019180MONDO:0019180
osteosarcoma1MONDO:0009807EFO:0000637
brain neoplasm1MONDO:0021211EFO:0003833
chronic hepatitis C virus infection1MONDO:0005354EFO:0004220
cystic, mucinous, and serous neoplasm1MONDO:0006720MONDO:0021077

8 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 246.

Phase distribution

PhaseTrials
PHASE2100
PHASE372
Not specified28
PHASE118
PHASE415
PHASE1/PHASE26
EARLY_PHASE14
PHASE2/PHASE33

Top trials by phase / activity

NCTPhaseStatusTitle
NCT05161195PHASE4ACTIVE_NOT_RECRUITINGRoll-over Study to Allow Continued Access to Ribociclib
NCT00537771PHASE4COMPLETEDLiver Safety Under Upfront Arimidex vs Tamoxifen
NCT00999921PHASE4COMPLETEDEffects of Tamoxifen in Premenopausal Women With Benign Breast Disease Not at High-Risk of Developing Breast Cancer
NCT01127295PHASE4COMPLETEDPharmacology of Adjuvant Hormonotherapy in Breast Cancer
NCT01189500PHASE4COMPLETEDOpen-Label Drug Interaction Study Evaluating Desvenlafaxine Succinate Sustained Release (DVS SR) 100mg On The Pharmacokinetics Of Tamoxifen When Coadministered To Healthy Post-Menopausal Female Subjects
NCT01612871PHASE4COMPLETEDCirculating miRNAs as Biomarkers of Hormone Sensitivity in Breast Cancer
NCT02070692PHASE4COMPLETEDTamoxifen for the Treatment of Unfavorable Bleeding in Contraceptive Implant Users
NCT02344940PHASE4COMPLETEDSafety of Toremifene and Tamoxifen Therapy in Premenopausal Patients With Operable Breast Cancer
NCT02467686PHASE4UNKNOWNBreast Cancer, Sexuality and Black Cohosh
NCT02479256PHASE4COMPLETEDClomiphene Citrate Versus Tamoxifen for Ovulation Induction in PCOs
NCT02690870PHASE4UNKNOWNTamoxifen and Clomiphene Citrate in Mild Stimulation IVF
NCT02824224PHASE4COMPLETEDTamoxifen to Reduce Unscheduled Bleeding in New Users of the Levonorgestrel-releasing Intrauterine System (LNG-IUS)
NCT02903121PHASE4COMPLETEDTreatment of Unfavorable Bleeding Patterns in Contraceptive Implant Users
NCT03060304PHASE4UNKNOWNThe Effect of Tamoxifen on Clinical Outcome in Women With Thin Endometrium Undergoing Frozen Thawed Cycle.
NCT05525481PHASE4UNKNOWNTamoxifen Prediction Study in Patients With ER+ Breast Cancer
NCT01357772PHASE3ACTIVE_NOT_RECRUITINGTrial of Low Dose Tamoxifen in Women With Breast Intraepithelial Neoplasia - Long Term Follow-up
NCT02062489PHASE3RECRUITINGEvaluation of Tamoxifen’s Efficacy for ER/PR Negative,ER-beta Positive Operable Breast Cancer Patients
NCT03011684PHASE3RECRUITINGFertility Preservation Using Tamoxifen and Letrozole in Estrogen Sensitive Tumors Trial
NCT04134598PHASE3ACTIVE_NOT_RECRUITINGExclUsive endocRine Therapy Or Radiation theraPy for Women Aged ≥70 Years Early Stage Breast Cancer
NCT04906395PHASE3ACTIVE_NOT_RECRUITINGOvarian Suppression Evaluating Subcutaneous Leuprolide Acetate in Breast Cancer
NCT05306340PHASE3ACTIVE_NOT_RECRUITINGA Study Evaluating the Efficacy and Safety of Giredestrant Plus Everolimus Compared With the Physician’s Choice of Endocrine Therapy Plus Everolimus in Participants With Estrogen Receptor-Positive, HER2-Negative, Locally Advanced or Metastatic Breast Cancer (evERA Breast Cancer)
NCT05512364PHASE3RECRUITINGElacestrant for Treating ER+/HER2- Breast Cancer Patients With ctDNA Relapse (TREAT ctDNA)
NCT05514054PHASE3ACTIVE_NOT_RECRUITINGA Study of Imlunestrant Versus Standard Endocrine Therapy in Participants With Early Breast Cancer
NCT05645536PHASE3ENROLLING_BY_INVITATIONSafety Extension Study for Subjects With HR+, HER2- Breast Cancer for Subjects Who Have Completed the OVELIA Study
NCT05774951PHASE3RECRUITINGA Study of Camizestrant in ER+/HER2- Early Breast Cancer After at Least 2 Years of Standard Adjuvant Endocrine Therapy
NCT05780567PHASE3ACTIVE_NOT_RECRUITINGClinical Study on Adjuvant Therapy of TQB3616 Combined With Endocrine Therapy Compared With Placebo Combined With Endocrine Therapy in Patients With Breast Cancer
NCT05891093PHASE3RECRUITINGEfficacy and Safety of Fluzoparib Combined With Adjuvant Endocrine Therapy for HR+/HER2- SNF3-subtype Early Breast Cancer (BCTOP-L-A01)
NCT05952557PHASE3RECRUITINGAn Adjuvant Endocrine-based Therapy Study of Camizestrant (AZD9833) in ER+/HER2- Early Breast Cancer (CAMBRIA-2)
NCT06223698PHASE3NOT_YET_RECRUITINGOptimizing Extended Adjuvant Endocrine Therapy in Patients With Breast Cancer
NCT06355401PHASE2/PHASE3NOT_YET_RECRUITINGMaintenance Hormonal Therapy and DLBCL
NCT06404775PHASE3NOT_YET_RECRUITINGExternal Mastalgia-oil Versus Oral Tamoxifen in Premenopausal Women with Severe Mastalgia
NCT06440967PHASE3ACTIVE_NOT_RECRUITINGA Study to Confirm if Fezolinetant Helps Reduce Hot Flashes in Women With Breast Cancer Who Are Having Hormone Therapy
NCT06492616PHASE3RECRUITINGA Study of Elacestrant Versus Standard Endocrine Therapy in Women and Men With ER+,HER2-, Early Breast Cancer With High Risk of Recurrence
NCT06507618PHASE3RECRUITINGPre-Operative Window of ET to Inform RT Decisions (POWER II)
NCT07190443PHASE3RECRUITINGAdjuvant Abemaciclib for Locoregional Recurrence of HR-positive, HER2-negative Breast Cancer (JCOG2313, AURA)
NCT00000529PHASE3COMPLETEDTamoxifen Study
NCT00002707PHASE3COMPLETEDChemotherapy in Treating Women With Breast Cancer That Can Be Surgically Removed
NCT00003906PHASE3COMPLETEDStudy of Tamoxifen and Raloxifene (STAR) for the Prevention of Breast Cancer in Postmenopausal Women
NCT00034125PHASE3COMPLETEDPhase 3 Study of LY353381 Vs Tamoxifen in Women With Locally Advanced or Metastatic Breast Cancer.
NCT00036270PHASE3COMPLETEDRandomized Phase III Study Of Exemestane (Aromasin) For 5 Years Versus Tamoxifen for 2.5 to 3 Years Followed By Exemestane

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (4) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of DPWG Guideline for tamoxifen and CYP2D6DPWGCYP2D6yesyes
Annotation of CPIC Guideline for tamoxifen and CYP2D6CPICCYP2D6yesyes
Annotation of CPNDS Guideline for tamoxifen and CYP2D6CPNDSCYP2D6yesyes
Annotation of RNPGx Guideline for tamoxifen and CYP2D6RNPGxCYP2D6

PharmGKB also curates 21 clinical and 282 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

178 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
ESTRADIOLChEMBL + PubChemPhase 4 (approved)ESR1, ESR2, GPER1
FulvestrantChEMBL + PubChemPhase 4 (approved)ESR1, ESR2, GPER1
RaloxifeneChEMBL + PubChemPhase 4 (approved)ESR1, ESR2, GPER1
BAZEDOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
BITHIONOLChEMBLPhase 4 (approved)ESR1, ESR2
CISPLATINChEMBLPhase 4 (approved)ESR1, ESR2
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)ESR1, ESR2
ELACESTRANTChEMBLPhase 4 (approved)ESR1, ESR2
ESTETROLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRIOLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRONEChEMBLPhase 4 (approved)ESR1, ESR2
ETHINYL ESTRADIOLChEMBLPhase 4 (approved)ESR1, ESR2
HEXACHLOROPHENEChEMBLPhase 4 (approved)ESR1, ESR2
LASOFOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
MEDROXYPROGESTERONEChEMBLPhase 4 (approved)ESR1, ESR2
MIFEPRISTONEChEMBLPhase 4 (approved)ESR1, ESR2
PHENOLPHTHALEINChEMBLPhase 4 (approved)ESR1, ESR2
SPIRONOLACTONEChEMBLPhase 4 (approved)ESR1, ESR2
ACOLBIFENEChEMBLPhase 3ESR1, ESR2
AFIMOXIFENEChEMBLPhase 3ESR1, ESR2
AMCENESTRANTChEMBLPhase 3ESR1, ESR2
ARZOXIFENEChEMBLPhase 3ESR1, ESR2
BENSERAZIDEChEMBLPhase 3ESR1, ESR2
ALFATRADIOLChEMBLPhase 2ESR1, ESR2
AUS-131ChEMBLPhase 2ESR1, ESR2
BRILANESTRANTChEMBLPhase 2ESR1, ESR2
DAIDZEINChEMBLPhase 2ESR1, ESR2
ERTEBERELChEMBLPhase 2ESR1, ESR2
GENISTEINChEMBLPhase 2ESR1, ESR2
GTX-758ChEMBLPhase 2ESR1, ESR2
IDOXIFENEChEMBLPhase 2ESR1, ESR2
LEVORMELOXIFENEChEMBLPhase 2ESR1, ESR2
MOXESTROLChEMBLPhase 2ESR1, ESR2
PIPENDOXIFENEChEMBLPhase 2ESR1, ESR2
PRINABERELChEMBLPhase 2ESR1, ESR2
STALLIMYCINChEMBLPhase 2ESR1, ESR2
BosentanPubChemApprovedESR1, ESR2
DihydroergotaminePubChemApprovedESR1, ESR2
FidaxomicinPubChemApprovedESR1, ESR2
PropoxyphenePubChemApprovedESR1, ESR2
PyrazinamidePubChemApprovedESR1, ESR2
ACETOPHENAZINEChEMBLPhase 4 (approved)ESR1
ALECTINIBChEMBLPhase 4 (approved)ESR1
APOMORPHINEChEMBLPhase 4 (approved)ESR1
ARIPIPRAZOLEChEMBLPhase 4 (approved)ESR1
ASPIRINChEMBLPhase 4 (approved)ESR1
AZTREONAMChEMBLPhase 4 (approved)ESR1
BELINOSTATChEMBLPhase 4 (approved)ESR1
BENZBROMARONEChEMBLPhase 4 (approved)ESR1
BEXAROTENEChEMBLPhase 4 (approved)ESR1
BISACODYLChEMBLPhase 4 (approved)ESR1
BROMOCRIPTINEChEMBLPhase 4 (approved)ESR1
BUTOCONAZOLEChEMBLPhase 4 (approved)ESR1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)ESR1
CASPOFUNGINChEMBLPhase 4 (approved)ESR1
CEFADROXILChEMBLPhase 4 (approved)ESR1
CEFEPIMEChEMBLPhase 4 (approved)ESR1
CEFTAZIDIMEChEMBLPhase 4 (approved)ESR1
CERIVASTATINChEMBLPhase 4 (approved)ESR1
CHLOROTRIANISENEChEMBLPhase 4 (approved)ESR1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot