Chlorotrianisene

Summary

Chlorotrianisene (CHEMBL1200761) is an approved small-molecule estrogen receptor modulator (ATC G03CA06); indicated across 2 conditions including hepatocellular carcinoma.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: G03CA06
• Indications: 2 conditions
• Clinical trials: 184
• Chemistry: 380.9 Da · C23H21ClO3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1200761
Name	Chlorotrianisene
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	11289
ChEBI	CHEBI:3641
ATC	G03CA06
Molecular formula	C23H21ClO3
Molecular weight	380.9
InChIKey	BFPSDSIWYFKGBC-UHFFFAOYSA-N

SMILES: COC1=CC=C(C=C1)C(=C(C2=CC=C(C=C2)OC)Cl)C3=CC=C(C=C3)OC

IUPAC name: 1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene

Pharmacological roles (ChEBI): estrogen receptor modulator, antineoplastic agent, xenoestrogen.

Also known as: Adam17, Chlorotrianisene, Clorotrianiseno, NSC-10108, Snake venom-like protease, Tace, Tnf-alpha convertase, Tnf-alpha-converting enzyme, SID11112416, SID11532856, SID17389725, SID26747338

Patent coverage: 6,668 distinct patent families (23,246 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

Broader ChEMBL bioactivity targets: 19 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Survival motor neuron protein, Prelamin-A/C, Ferritin light chain, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Thyrotropin receptor, Estrogen receptor, Alpha-1A adrenergic receptor, Adenosine receptor A3, Cruzipain, Aldehyde dehydrogenase 1A1, Cytochrome P450 2C19, Mitogen-activated protein kinase 1, Prostaglandin G/H synthase 1, 3-hydroxyacyl-CoA dehydrogenase type-2, Hypoxia-inducible factor 1-alpha, Lethal factor, Neuropeptide S receptor.

Bioactivity

ChEMBL activities: 10 potent at pChembl ≥ 5 of 30 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
Q63921	7.11	AC50	78.2	nM	CHEMBL_ACT_25173866
CYP2C19	7	Potency	100	nM	CHEMBL_ACT_4021225
CYP2C19	7	AC50	100	nM	CHEMBL_ACT_6004029
Q63921	6.59	AC50	259.2	nM	CHEMBL_ACT_25174839
LMNA	6.55	Potency	281.8	nM	CHEMBL_ACT_3623589
ESR1	6.09	AC50	817.1	nM	CHEMBL_ACT_25167693
MAPT	5.25	Potency	5623	nM	CHEMBL_ACT_4502249
NPSR1	5.1	Potency	7943	nM	CHEMBL_ACT_4912741
HIF1A	5	Potency	10000	nM	CHEMBL_ACT_4129723
HIF1A	5	Potency	10000	nM	CHEMBL_ACT_4518759

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 disease in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
hepatocellular carcinoma	3	MONDO:0007256	EFO:0000182

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

Clinical trials

Total trials: 184.

Phase distribution

Phase	Trials
Not specified	66
PHASE2	50
PHASE3	31
PHASE2/PHASE3	13
PHASE1/PHASE2	12
PHASE4	7
PHASE1	5

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00554905	PHASE4	UNKNOWN	Radiofrequency Ablation With or With Transcatheter Arterial Embolization for Hepatocellular Carcinoma
NCT00868569	PHASE4	UNKNOWN	Transhepatic Arterial Chemotherapy (TAC) Versus Transcatheter Arterial Chemoembolization (TACE) Plus Folfox4 as the Treatment of Unresectable Liver Metastasis of Colorectal Cancer
NCT01332669	PHASE4	COMPLETED	Drug-eluting Bead in Hepatocellular Carcinoma
NCT01350206	PHASE4	UNKNOWN	Hepatic Resection Versus Transcatheter Arterial Chemoembolization for Hepatocellular Carcinoma Complicated by Portal Vein Tumor Thrombosis
NCT01952353	PHASE4	COMPLETED	Preoperative Transarterial Chemoembolization for Resectable HCC With Portal Venous Invasion
NCT02504983	PHASE4	UNKNOWN	Clinical Trial for GALNT14 Genotype - Guided, Sorafenib in Combination With TACE in Hepatocellular Carcinoma
NCT02631499	PHASE4	UNKNOWN	Efficacy Study of TACE to Treat Hepatocellular Carcinoma After Operation
NCT04803994	PHASE3	RECRUITING	The ABC-HCC Trial: Atezolizumab Plus Bevacizumab vs. Transarterial Chemoembolization (TACE) in Intermediate-stage HepatoCellular Carcinoma
NCT05320692	PHASE3	ACTIVE_NOT_RECRUITING	A Study of TACE Combined With Camrelizumab Plus Rivoceranib (Apatinib) in Patients With Incurable Hepatocellular Carcinoma
NCT05718232	PHASE3	NOT_YET_RECRUITING	SBRT Plus Lenvatinib and TACE for Advanced Primary HCC: A Phase 3 Trial (SEARCH)
NCT06371157	PHASE3	RECRUITING	A Study of AK104+Lenvatinib in Combination With Transarterial Chemoembolization (TACE) Versus TACE in Participants With Incurable/Non-metastatic Hepatocellular Carcinoma
NCT06844357	PHASE2/PHASE3	RECRUITING	A Phase II/III Trial Comparing Transarterial Tirapazamine Embolization (TATE) With cTACE for Intermediate-stage Liver Cancer.
NCT07186621	PHASE3	RECRUITING	Adjuvant Radiotherapy of Sintilimab Versus TACE for HCC
NCT07309419	PHASE2/PHASE3	NOT_YET_RECRUITING	A Phase III Randomized Study of TACE Plus an Oral Triple-Agent Cocktail Versus TACE Plus First-Line Targeted Immunotherapy in Unresectable Hepatocellular Carcinoma
NCT00467974	PHASE3	COMPLETED	Transarterial Ethanol Ablation (TEA) Versus Transcatheter Arterial Chemoembolisation (TACE) for Hepatocellular Carcinoma
NCT00522405	PHASE2/PHASE3	UNKNOWN	Randomized Control Trial (RCT) of Transarterial Chemoembolization (TACE) Versus TACE and Oral Drug Therapy in the Treatment of Unresectable Hepatocellular Carcinoma
NCT00827554	PHASE2/PHASE3	COMPLETED	The Role of Low Molecular Weight Heparins in Hepatocellular Carcinoma
NCT00908752	PHASE3	COMPLETED	Phase III Trans-Arterial Chemo-Embolization (TACE) Adjuvant HCC
NCT00921531	PHASE3	UNKNOWN	Adjuvant Therapy With Thalidomide for Chemoembolization in Advanced Hepatocellular Carcinoma
NCT01327521	PHASE3	WITHDRAWN	Transarterial Chemoembolization vs CyberKnife for Recurrent Hepatocellular Carcinoma
NCT01833286	PHASE3	UNKNOWN	TACE+RFA Versus Re-resection for Recurrent Small Hepatocellular Carcinoma
NCT01833299	PHASE3	COMPLETED	Transcatheter Arterial Chemoembolization Combined With Sorafenib for Unresectable Hepatocellular Carcinoma
NCT01901692	PHASE2/PHASE3	COMPLETED	Sorafenib vs.TransArterial Chemoembolization Plus RadioTherapy in Hepatocellular Carcinoma With Macrovascular Invasion
NCT01906216	PHASE3	COMPLETED	Sorafenib Chemoembolization Evaluation Controlled Trial
NCT02301091	PHASE3	UNKNOWN	Combine TACE and RFA Versus TACE Alone for HCC With PVTT
NCT02338297	PHASE3	UNKNOWN	Therapeutic Effect of Ethanol-gelfoam Mixture for the Treatment of Arterioportal Shunts (APS) in Patients With HCC
NCT02435953	PHASE3	COMPLETED	TACE+RFA Versus TACE Alone for Intermediate-stage Hepatocellular Carcinoma
NCT02436902	PHASE3	UNKNOWN	Adjuvant Therapies for Patients With HCC and MVI
NCT02568748	PHASE3	UNKNOWN	Evaluation of Cytokine-induced Killer (CIK) Cells as Therapy or Adjuvant Treatment for Advanced HCC
NCT02702323	PHASE2/PHASE3	UNKNOWN	Treatment Patients With Pulmonary Metastasis of Liver Cancer With Apatinib Combination With TACE: a Clinical Study
NCT02715492	PHASE3	UNKNOWN	Role of (LMWH) in Prevention of Thromboembolic Complication After (TACE) in Hepatocellular Carcinoma.
NCT02788526	PHASE3	COMPLETED	Adjuvant TACE to Reduce the HCC Recurrence After Resection
NCT02794337	PHASE2/PHASE3	UNKNOWN	TACE vs TACE+SBRT for Unresectable Hepatocellular Cancer
NCT02856126	PHASE3	COMPLETED	HAIC Plus Sorafenib Versus TACE Plus Sorafenibfor Advanced HCC
NCT03175016	PHASE2/PHASE3	UNKNOWN	Irinotecan-Eluting Bead (DEBIRI) for Patients With Liver Metastases From Colorectal Cancer
NCT03192644	PHASE3	UNKNOWN	The Impact on Recurrence Risk of Adjuvant Transarterial Chemoinfusion (TAI) Versus Adjuvant Transarterial Chemoembolization (TACE) for Patients With Hepatocellular Carcinoma And Portal Vein Tumor Thrombosis (PVTT) After Hepatectomy : A Random, Controlled, Stage III Clinical Trial.
NCT03783559	PHASE3	UNKNOWN	TACE(Transcatheter Arterial Chemoembolization ) Associated With Systemic Chemotherapy Versus Systemic Chemotherapy Alone in Patients With Unresectable CRLM(Colorectal Liver Metastases)
NCT03791918	PHASE3	WITHDRAWN	Lenvatinib Plus PD-1 Antibody vs TACE for Intermediate-stage HCC Beyond Up-to-seven Criteria
NCT03905967	PHASE3	UNKNOWN	TACE With Lenvatinib Versus Lenvatinib Alone in in First-line Treatment of Advanced HCC
NCT03939845	PHASE3	UNKNOWN	A Prospective, Randomized, Multicenter Study of Comparison of TACE Combination With and Without EBRT for Hepatocellular Carcinoma With Portal Vein Tumor Thrombi
NCT04103398	PHASE3	COMPLETED	TACE Plus Sorafenib Versus TACE Alone for Recurrent Intermediate Hepatocellular Carcinoma
NCT04246177	PHASE3	COMPLETED	Safety and Efficacy of Lenvatinib (E7080/MK-7902) With Pembrolizumab (MK-3475) in Combination With Transarterial Chemoembolization (TACE) in Participants With Incurable/Non-metastatic Hepatocellular Carcinoma (MK-7902-012/E7080-G000-318/LEAP-012)
NCT04268888	PHASE2/PHASE3	SUSPENDED	Nivolumab in Combination With TACE/TAE for Patients With Intermediate Stage HCC
NCT04340193	PHASE3	COMPLETED	A Study of Nivolumab and Ipilimumab and Nivolumab Alone in Combination With Trans-arterial ChemoEmbolization (TACE) in Participants With Intermediate Stage Liver Cancer
NCT04387695	PHASE3	UNKNOWN	SBRT+TACE+Sorafenib Vs Sorafenib in the Treatment of uHCC With PVTT
NCT04909866	PHASE2/PHASE3	UNKNOWN	The Efficacy and Safety of TACE, Lenvatinib and Camrelizumab in the Treatment of BCLC Stage B/C Hepatocellular Carcinoma: a Single-arm, Single-center, Open-label Study
NCT05056337	PHASE3	UNKNOWN	Toripalimab in Combination With Lenvatinib and TACE for Conversion Therapy in Patients With Potentially Resectable HCC
NCT05171166	PHASE2/PHASE3	TERMINATED	Neoadjuvant HAIC of TACE Plus Donafenib in BCLC B Stage HCC: a Multi-center Randomized Controlled Trial.
NCT05250843	PHASE2/PHASE3	UNKNOWN	TACE/HAIC Combined With Lenvatinib and Sintilimab in Neoadjuvant Therapy for Intermediate-stage HCC
NCT05344924	PHASE2/PHASE3	UNKNOWN	TACE Combined With Penpulimab and Anlotinib for Advanced HCC
NCT05647954	PHASE3	UNKNOWN	A Study of HX008 Plus Transcatheter Arterial Chemoembolization (TACE) in the First-Line Treatment of Subjects With Stage IV (M1c) Melanoma That is Metastatic to the Liver
NCT03937830	PHASE2	ACTIVE_NOT_RECRUITING	Combined Treatment of Durvalumab, Bevacizumab, Tremelimumab and Transarterial Chemoembolization (TACE) in Subjects With Hepatocellular Carcinoma or Biliary Tract Carcinoma
NCT04954781	PHASE2	RECRUITING	TACE Combined With Tislelizumab in Patients With Advanced Intrahepatic Cholangiocarcinoma
NCT04988945	PHASE2	RECRUITING	TACE and SBRT Followed by Double Immunotherapy for Downstaging Hepatocellular Carcinoma
NCT05319431	PHASE2	ACTIVE_NOT_RECRUITING	A Phase II Study of AK104 Plus Lenvatinib and TACE in HCC
NCT05920863	PHASE2	RECRUITING	Lenvatinib Combined with Tislelizumab and TACE Applied As Neoadjuvant Regimen for the Patients of CNLC Stage IB and IIA Hepatocellular Carcinoma with High-risk Recurrence Factors
NCT06896396	PHASE1/PHASE2	NOT_YET_RECRUITING	Icaritin Soft Capsules+TACE+Immunotherapy+Targeted Therapy Versus TACE+Immunotherapy+Targeted Therapy for Unresectable Hepatocellular Carcinoma
NCT06900478	PHASE2	NOT_YET_RECRUITING	Icariin Soft Capsules Combined With TACE as Adjuvant Therapy for HCC
NCT06995105	PHASE1/PHASE2	RECRUITING	Personalized Tumor Neoantigen mRNA Therapy for Advanced Hepatocellular Carcinoma
NCT07128251	PHASE2	NOT_YET_RECRUITING	A Single-Arm, Multicenter, Exploratory Clinical Study of Transarterial Chemoembolization (TACE) Combined With Iparomlimab and Tuvonralimab Injection and Bevacizumab Injection for the Treatment of Unresectable, Non-Metastatic Hepatocellular Carcinoma (HCC)
NCT07131501	PHASE2	NOT_YET_RECRUITING	A Single-Arm, Multicenter, Exploratory Clinical Study of TACE Combined With Iparomlimab and Tuvonralimab Injection (QL1706) and Lenvatinib for Perioperative Treatment of Resectable Hepatocellular Carcinoma
NCT07138885	PHASE2	ACTIVE_NOT_RECRUITING	A Phase II, Single-Arm, Prospective Trial on the Efficacy and Safety of QL1706 Combination Regimen as Second-Line Therapy for Targeted-Immunotherapy-Resistant Hepatocellular Carcinoma
NCT07157969	PHASE2	RECRUITING	ICIs and Anti-VEGF Antibody/TKIs With or Without Interventional Therapy for Advanced HCC
NCT07187284	PHASE1/PHASE2	NOT_YET_RECRUITING	EDN Combined With TACE/HAIC and Second-Line Immune-Targeted Treatment Versus TACE/HAIC Alone in Locally Advanced HCC With Portal Vein Tumor Thrombosis After First-Line Therapy Failure: A Prospective, Multicenter, Randomized Controlled Trial
NCT07380633	PHASE2	ACTIVE_NOT_RECRUITING	Toripalimab Plus Bevacizumab Combined Three Intra-arterial Therapies (TACE, HAIC, or TACE-HAIC) for Unresectable Hepatocellular Carcinoma: a Phase 2, Multicenter Randomised Non-comparative Trial
NCT07398664	PHASE2	NOT_YET_RECRUITING	H101 Plus TACE for r/m HNSCC
NCT07487662	PHASE2	NOT_YET_RECRUITING	TACE or Ablation Combined With Sintilimab and Ipilimumab N01 as Neoadjuvant Therapy for Resectable Hepatocellular Carcinoma With Intermediate-High Recurrence Risk
NCT07521852	PHASE2	RECRUITING	A Phase IIa, Single-arm, Open-label Clinical Study to Evaluate the Efficacy, Safety and PK of CVM-1118 in Combination With Sintilimab and TACE in Participants With Incurable/Non-metastatic HCC
NCT00576056	PHASE2	TERMINATED	Effectiveness and Safety Study of TACE Plus Oral Sorafenib for Unresectable HCC
NCT00960518	PHASE2	UNKNOWN	TACE and Adefovir Compared With Transarterial Chemoembolization (TACE) Alone for Hepatitis B Virus (HBV)-Related Unresectable Hepatocellular Carcinoma (HCC)
NCT01020812	PHASE1/PHASE2	TERMINATED	Combination SBRT With TACE for Unresectable Hepatocellular Carcinoma
NCT01217034	PHASE2	UNKNOWN	Transcatheter Arterial Chemoembolization Therapy In Combination With Sorafenib
NCT01300143	PHASE2	COMPLETED	Association of Conformational High-dose Radiotherapy and of Hyperselective Transarterial Chemoembolization in the Treatment of Hepatocellular Carcinoma
NCT01605734	PHASE2	UNKNOWN	TACE Combinated With Sorafenib in Treating Patients With Unresectable Hepatocellular Carcinoma
NCT01715532	PHASE2	UNKNOWN	Role of Huachansu in Treating Hepatocellular Carcinoma and the Correlation With Na+/K+-ATPase
NCT01853618	PHASE1/PHASE2	COMPLETED	Tremelimumab With Chemoembolization or Ablation for Liver Cancer
NCT02015754	PHASE2	COMPLETED	Irinotecan -Eluting LC Bead-M1 (DEBIRI-M1) for Patients With Liver Metastases From Colorectal Cancer
NCT02418988	PHASE2	UNKNOWN	Trans-catheter Chemo-embolization Combined With rAd-p53 Gene Injection in Treatment of Advanced Hepatocellular Carcinoma
NCT02513199	PHASE2	COMPLETED	Combination Chemoembolization and Stereotactic Body Radiation Therapy in Unresectable Hepatocellular Carcinoma
NCT02638857	PHASE1/PHASE2	UNKNOWN	Immunotherapy Using Precision T Cells Specific to Multiple Common Tumor-Associated Antigen Combined With Transcatheter Arterial Chemoembolization for the Treatment of Advanced Hepatocellular Carcinoma
NCT02821533	PHASE2	TERMINATED	Chemoembolization for Hepatocellular Carcinoma
NCT02862613	PHASE1/PHASE2	UNKNOWN	Precision Cell Immunotherapy Combined With TACE in Advanced Liver Cancer
NCT02873442	PHASE1/PHASE2	UNKNOWN	Precision Cell Immunotherapy Combined With TACE in Advanced Liver Cancer
NCT02956772	PHASE2	UNKNOWN	Transcatheter Arterial Chemoembolization (TACE) in Combination With Arsenic Trioxide Versus TACE in the Treatment of Middle-advanced Primary Hepatocellular Carcinoma (HCC) Patients
NCT03086564	PHASE1/PHASE2	COMPLETED	A Basic-clinical Translational Research in Hepatitis B Virus (HBV)-Specific Antigen Peptides and HepG2 Cell Lysate Co-activated Dendritic Cells Combined With Transarterial Chemoembolization (TACE) in HBV-related HCC Treatment (BTRHBVAPHCLCDCCTCHBVHCCT)
NCT03510416	PHASE2	UNKNOWN	Efficacy and Safety of Apatinib Combined With TACE in Patients With Hepatocellular Carcinoma
NCT03572582	PHASE2	COMPLETED	Transarterial Chemoembolization in Combination With Nivolumab Performed for Intermediate Stage Hepatocellular Carcinoma
NCT03575806	PHASE2	COMPLETED	Combine TACE and Autologous Tcm Immunotherapy Versus TACE Alone for HCC With MVI After Radical Resection
NCT03608878	PHASE2	TERMINATED	Adagloxad Simolenin/OBI-821 in Combination With TACE Therapy in HCC Patients With GALNT14-rs9679162-non-TT Genotype
NCT03782831	PHASE2	WITHDRAWN	TACE Plus PD-1 Antibody vs TACE Alone for Unresectable HCC
NCT03817736	PHASE2	COMPLETED	Sequential TACE and SBRT Followed by ImmunoTherapy for Downstaging HCC for Hepatectomy
NCT04011033	PHASE2	COMPLETED	Study of Adoptive Transfer of iNKT Cells Combined With TAE/TACE to Treat Unresectable HCC
NCT04066543	PHASE2	UNKNOWN	TACE Combined With Anlotinib Treatment of Middle-advanced Hepatocellular Carcinoma (HCC) Patients
NCT04157140	PHASE2	UNKNOWN	Anlotinib In Combination With RFA And TACE in Patients With Middle-advanced HCC
NCT04213118	PHASE2	UNKNOWN	Anlotinib Combined With TACE in Hepatocellular Carcinoma Patients at High Risk of Post Surgery Recurrence
NCT04297280	PHASE2	COMPLETED	TACE Combined with Anti-PD-1 Antibody in Patients with Advanced Hepatocellular Carcinoma
NCT04490694	PHASE2	UNKNOWN	TACE Combined With Lenvatinib for Unresectable Hepatocellular Carcinoma
NCT04653389	PHASE2	TERMINATED	Perioperative Therapy for Hepatocellular Carcinoma
NCT04842565	PHASE2	COMPLETED	cTACE Plus Sintilimab for Unresectable Intermediate-stage HCC With Beyond Up-to-seven Criteria
NCT04911959	PHASE1/PHASE2	UNKNOWN	Study of TACE Combined With Lenvatinib to Prevent Postoperative Recurrence in Patients With MVI Positive HCC

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).