Estramustine

Summary

Estramustine (CHEMBL1575) is a phase-3 clinical-stage small-molecule antineoplastic agent (ATC L01XX11); indicated across 5 conditions including neoplasm and metastatic prostate carcinoma.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• ATC class: L01XX11
• Indications: 5 conditions
• Clinical trials: 20
• Chemistry: 440.4 Da · C23H31Cl2NO3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1575
Name	Estramustine
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	259331
ChEBI	CHEBI:4868
ATC	L01XX11
Molecular formula	C23H31Cl2NO3
Molecular weight	440.4
InChIKey	FRPJXPJMRWBBIH-RBRWEJTLSA-N

SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl

IUPAC name: [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate

ChEBI definition: A carbamate ester obtained by the formal condensation of the hydroxy group of 17β-estradiol with the carboxy group of bis(2-chloroethyl)carbamic acid.

Pharmacological roles (ChEBI): antineoplastic agent, alkylating agent, radiation protective agent.

Also known as: Estramustina, Estramustine, LEO-275, LEO275, NSC-89201, RO-222296000, estramustin, SID26758003, estramustine, SID396503, ESTRAMUSTINE, SID144205760

Patent coverage: 19,413 distinct patent families (83,283 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 82,628 (99%) of the total. 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: 2 (assay-derived). Sample: ATP-dependent DNA helicase Q1, RecQ-like DNA helicase BLM.

Bioactivity

ChEMBL activities: 1 potent at pChembl ≥ 5 of 3 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
RECQL	5.09	Potency	8135	nM	CHEMBL_ACT_5056230

Target pathways

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

Indications & clinical

Indications

5 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
metastatic prostate carcinoma	3	MONDO:0004956	EFO:0000196
prostate adenocarcinoma	3	MONDO:0005082	EFO:0000673
breast neoplasm	2	MONDO:0021100	MONDO:0007254

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

Clinical trials

Total trials: 20.

Phase distribution

Phase	Trials
PHASE2	14
PHASE1/PHASE2	4
PHASE3	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00004001	PHASE3	COMPLETED	S9916, Combination Therapy in Treating Patients With Advanced Prostate Cancer That Has Not Responded to Hormone Therapy
NCT00705822	PHASE3	TERMINATED	Combination of Docetaxel + Estramustine + Hydrocortisone Versus Docetaxel + Prednisone in Patients With Advanced Prostate Cancer
NCT00016913	PHASE2	COMPLETED	Chemotherapy, Hormone Therapy, and Radiation Therapy in Treating Patients With Locally Advanced Prostate Cancer
NCT00028769	PHASE2	COMPLETED	S0032, Combination Chemotherapy Plus Hormone Therapy in Treating Patients With Metastatic Prostate Cancer
NCT00038168	PHASE1/PHASE2	COMPLETED	Intravenous Estramustine With Taxol in Hormone Refractory Prostate Adenocarcinoma
NCT00038246	PHASE1/PHASE2	COMPLETED	Study of Paclitaxel, Estramustine Phosphate and Thalidomide for Patients With Metastatic Androgen-Independent Prostate Carcinoma
NCT00132756	PHASE1/PHASE2	TERMINATED	Liposomal Doxorubicin and Estramustine Phosphate: Study in Taxane Resistant, Hormone Refractory Advanced Prostate Cancer
NCT00151060	PHASE2	COMPLETED	Estramustine, Etoposide and Paclitaxel Treatment for Hormonally Responsive Adenocarcinoma of the Prostate
NCT00151073	PHASE2	COMPLETED	Estramustine, Docetaxel and Zoledronate Treatment in Hormone-Refractory Adenocarcinoma of the Prostate
NCT00151086	PHASE1/PHASE2	COMPLETED	Oral Estramustine and Oral Vinorelbine in the Treatment of Hormone-Refractory Prostate Cancer
NCT00165399	PHASE2	COMPLETED	Docetaxel, Estramustine and Short Term Androgen Withdrawal for Patients With a Rising PSA After Local Treatment
NCT00183924	PHASE2	COMPLETED	Estramustine, Docetaxel, and Carboplatin for Patients With Hormone Refractory Prostate Cancer Progressing After Mitoxantrone-Based Chemotherapy.
NCT00193193	PHASE2	COMPLETED	Weekly Paclitaxel, Low-Dose Estramustine, and Carboplatin in the Treatment of Hormone Refractory Prostate Carcinoma
NCT00193271	PHASE2	COMPLETED	Adjuvant Docetaxel and Estramustine Phosphate for High Risk Localized Prostate Cancer
NCT00541281	PHASE2	COMPLETED	Safety and Efficacy Study of of Docetaxel vs Docetaxel Estramustine in Hormone Refractory Prostatic Cancer
NCT01250717	PHASE2	COMPLETED	Docetaxel Followed by Radical Prostatectomy in Patients With High Risk Localized Prostate Cancer
NCT02494713	PHASE2	TERMINATED	Hormonal Therapy and Chemotherapy Followed by Prostatectomy in Patients With Prostate Cancer
NCT02560051	PHASE2	TERMINATED	Hormone Therapy Plus Chemotherapy as Initial Treatment for Local Failures or Advanced Prostate Cancer
NCT02853071	PHASE2	WITHDRAWN	Efficacy and Safety of Estracyt® in Metastatic Breast Cancer
NCT02866955	PHASE2	COMPLETED	Evaluation of the Efficacy of Estramustine in Patient With Breast Cancer Progression After Treatment With Aromatase Inhibitor.

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

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