Toremifene
drugOn this page
Also known as AcapodeneChlortamoxifenFarestoneGTX-006J33.157KToremifenoToremipheneSID29216214TOREMIFENE CITRATE
Summary
Toremifene (CHEMBL1655) is an approved small-molecule antineoplastic agent (ATC L02BA02); indicated across 10 conditions including neoplasm and prostate intraepithelial neoplasia.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: L02BA02
- Indications: 10 conditions
- Clinical trials: 29
- Chemistry: 406 Da · C26H28ClNO
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1655 |
| Name | Toremifene |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 3005573 |
| ChEBI | CHEBI:9635 |
| ATC | L02BA02 |
| Molecular formula | C26H28ClNO |
| Molecular weight | 406 |
| InChIKey | XFCLJVABOIYOMF-QPLCGJKRSA-N |
SMILES: CN(C)CCOC1=CC=C(C=C1)/C(=C(/CCCl)\C2=CC=CC=C2)/C3=CC=CC=C3
IUPAC name: 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine
Pharmacological roles (ChEBI): antineoplastic agent, estrogen antagonist, estrogen receptor modulator, bone density conservation agent.
Also known as: Acapodene, Chlortamoxifen, Farestone, GTX-006, J33.157K, Toremifene, Toremifeno, Toremiphene, SID29216214, toremifene, TOREMIFENE, TOREMIFENE CITRATE
Parent form; salt/anhydrous children: CHEMBL1200675
Patent coverage: 16,892 distinct patent families (70,777 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).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| Maxi Cl- |
Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: Prelamin-A/C, 5-hydroxytryptamine receptor 6, Envelope glycoprotein.
Bioactivity
ChEMBL activities: 3 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| Q05320 | 7.2 | EC50 | 62.8 | nM | CHEMBL_ACT_20673466 |
| Q05320 | 7.2 | EC50 | 62.8 | nM | CHEMBL_ACT_20673469 |
| HTR6 | 5.38 | Ki | 4125 | nM | CHEMBL_ACT_12059586 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
10 indications (0 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).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| neoplasm | 3 | MONDO:0005070 | EFO:0000616 |
| prostate intraepithelial neoplasia | 3 | MONDO:0005193 | EFO:0002621 |
| breast neoplasm | 3 | MONDO:0021100 | EFO:0003869 |
| bone fracture | 3 | MONDO:0005315 | EFO:0003931 |
| desmoid tumor | 2 | MONDO:0007608 | EFO:0009907 |
| ovarian cancer | 2 | MONDO:0008170 | MONDO:0008170 |
| severe acute respiratory syndrome | 2 | MONDO:0005091 | MONDO:0100096 |
3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 29.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 14 |
| PHASE2 | 9 |
| Not specified | 3 |
| PHASE4 | 2 |
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT02344940 | PHASE4 | COMPLETED | Safety of Toremifene and Tamoxifen Therapy in Premenopausal Patients With Operable Breast Cancer |
| NCT03238703 | PHASE4 | WITHDRAWN | Endocrine Therapy in Treating Patients With HER2 Negative, Low Risk Breast Cancer |
| NCT05891093 | PHASE3 | RECRUITING | Efficacy and Safety of Fluzoparib Combined With Adjuvant Endocrine Therapy for HR+/HER2- SNF3-subtype Early Breast Cancer (BCTOP-L-A01) |
| NCT00002529 | PHASE3 | COMPLETED | Hormone Therapy and Chemotherapy in Treating Perimenopausal or Postmenopausal Women With Node-Positive Breast Cancer |
| NCT00010322 | PHASE3 | TERMINATED | Toremifene With or Without Atamestane in Treating Postmenopausal Women With Metastatic Breast Cancer |
| NCT00044291 | PHASE3 | COMPLETED | Phase III Study of Atamestane Plus Toremifene Versus Letrozole in Advanced Breast Cancer |
| NCT00097344 | PHASE3 | TERMINATED | The CAT Study: Atamestane Plus Toremifene Versus Letrozole in Advanced Breast Cancer |
| NCT00106691 | PHASE3 | COMPLETED | Prostate Cancer Prevention Study for Men With High Grade PIN (Prostatic Intraepithelial Neoplasia) |
| NCT00129142 | PHASE3 | COMPLETED | Toremifene Citrate for Prevention of Bone Fractures in Men With Prostate Cancer on Androgen Deprivation Therapy |
| NCT00267553 | PHASE3 | TERMINATED | Treatment and Survival Continuation Study of Atamestane Plus Toremifene vs Letrozole in Advanced Breast Cancer |
| NCT00534846 | PHASE3 | COMPLETED | The Effect of Toremifene Treatment to the Magnetic Resonance Imaging (MRI) Findings in Premenstrual Mastalgia |
| NCT01214291 | PHASE3 | WITHDRAWN | Efficacy and Safety Study of Toremifene Citrate for the Reduction in the Risk of New Bone Fracture Occurrences in Men With Prostate Cancer |
| NCT01417754 | PHASE3 | COMPLETED | Changes in Breast 3D Ultrasound Measurements Using Toremifene |
| NCT02097459 | PHASE3 | UNKNOWN | Prognostic Evaluation of Changing Endocrine Therapy in Women With Breast Cancer |
| NCT02132390 | PHASE3 | UNKNOWN | Adjuvant Toremifene With or Without Goserrelin in Premenopausal Women With Stage I-IIIA, Hormonal Receptor Positive Breast Cancer Accompanied With or Without Chemotherapy Induced Amenorrhoea |
| NCT03351062 | PHASE3 | UNKNOWN | Efficacy of Tamoxifen Versus Toremifene in CYP2D6 IM/PM of Premenopausal Patients With ER-positive Early Breast Cancer |
| NCT05472792 | PHASE2 | RECRUITING | Compare Adjuvant Monotherapy With Endocrine or Accelerated Partial Breast Irradiation After Lumpectomy |
| NCT00002595 | PHASE2 | COMPLETED | Toremifene in Treating Patients With Desmoid Tumors |
| NCT00003865 | PHASE2 | WITHDRAWN | Toremifene in Treating Patients With Ovarian Cancer |
| NCT00020735 | PHASE2 | COMPLETED | Toremifene Followed by Radical Prostatectomy in Treating Patients With Stage I or Stage II Prostate Cancer |
| NCT00028353 | PHASE2 | COMPLETED | A Chemoprevention Study of an Investigational Drug in Men With High Grade Prostate Intraepithelial Neoplasia (PIN) |
| NCT00437359 | PHASE2 | TERMINATED | Antiestrogen vs Aromatase Inhibitor After Adjuvant Chemotherapy for Breast Cancer |
| NCT02353429 | PHASE2 | UNKNOWN | Toremifene in Desmoid Tumor: Prospective Clinical Trial and Identification of Potential Molecular Targets |
| NCT02506790 | PHASE2 | UNKNOWN | Neoadjuvant Toremifene With Melatonin or Metformin in Locally Advanced Breast Cancer |
| NCT04531748 | PHASE2 | WITHDRAWN | Selective Estrogen Modulation and Melatonin in Early COVID-19 |
| NCT02271282 | PHASE1 | COMPLETED | Estradiol-Receptor Blockade in Older Men and Women |
| NCT03925233 | Not specified | UNKNOWN | Breast Cancer Treatment Based on Organ-like Culture |
| NCT04666805 | Not specified | UNKNOWN | Effect of Endocrine Therapy Duration on Clinical Outcome of Patients With HR+ Intraductal Carcinoma of the Breast |
| NCT05801705 | Not specified | UNKNOWN | Comparative Evaluation of Efficacy and Safety of Toremifene, Tamoxifen, and Aromatase Inhibitor Plus Ovarian Function Suppression in Hormone Receptor-Positive Early Breast Cancer Among Non-Low-Risk Premenopausal Women: A Real-World Study |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).