Estramustine

Base Information

• Chemical Name: Estramustine
• CAS No.: 2998-57-4
• Molecular Formula: C23H31Cl2NO3
• Molecular Weight: 440.41
• European Community (EC) Number: 221-076-3
• NSC Number: 89201
• UNII: 35LT29625A
• DSSTox Substance ID: DTXSID8046458
• Nikkaji Number: J7.659G
• Wikipedia: Estramustine
• Wikidata: Q412939
• NCI Thesaurus Code: C479
• RXCUI: 4089
• Metabolomics Workbench ID: 35296
• ChEMBL ID: CHEMBL1575
• Mol file: 2998-57-4.mol

Synonyms:Emcyt;Estracyt;Estramustin Phosphate;Estramustine;Estramustine Phosphate Sodium;Estramustinphosphate;Leo 275;Leo-275;Leo275;NSC 89199;NSC-89199;NSC89199;Phosphate Sodium, Estramustine;Phosphate, Estramustin

Chemical Property of Estramustine

Chemical Property:

• Vapor Pressure: 1.23E-13mmHg at 25°C
• Melting Point: 104.5 °C
• Refractive Index: 1.576
• Boiling Point: 565.751 °C at 760 mmHg
• PKA: 15.05±0.40(Predicted)
• Flash Point: 295.956 °C
• PSA: 49.77000
• Density: 1.253 g/cm³
• LogP: 5.18200
• Water Solubility.: 1mg/L(30 oC)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 439.1680992
• Heavy Atom Count: 29
• Complexity: 585

Purity/Quality:

99%, ^*data from raw suppliers

Estradiol3-[N,N-Bis(2-chloroethyl)carbamate] ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
• Recent ClinicalTrials: Evaluation of the Efficacy of Estramustine in Patient With Breast Cancer Progression After Treatment With Aromatase Inhibitor.
• Recent EU Clinical Trials: KEES- A single arm phase II trial of the peroral regimen KEES (Ketokonazole, Etoposide, Estramustine, Sendoxan) in patients with Castration Resistant Prostate Cancer (CRPC)
• Recent NIPH Clinical Trials: Study of the usefulness of neoadjuvant chemo-hormone therapy for high-risk prostate cancer
• Uses: Antineoplastic. Estradiol 3-[N,N-Bis(2-chloroethyl)carbamate] is used treatment of breast cancer. Also used in the treatment of prostate cancer.
• Indications: Estramustine phosphate sodium (Emcyt) is a hybrid structure combining estradiol and a nitrogen mustard in a single molecule. The drug has been approved for use in prostatic carcinomas and will produce clinical remissions in one-third of patients who have failed to respond to previous estrogen therapy. The mechanism of action of estramustine is not well defined, but it does not appear to require either alkylation of DNA or the presence of estrogen receptors in tumor cells. Nonetheless, the toxicities of the drug are similar to those of estrogen therapy: breast tenderness and enlargement (gynecomastia), fluid retention, mild nausea, and an increased risk of thrombophlebitis and pulmonary embolism.The drug is not myelosuppressive.
• Biological Functions: Estramustine has a low affinity for the βm tubulin isotype, which often is overexpressed in estramustineresistant prostatic neoplasms as one defense against this therapeutic intervention.

Technology Process of Estramustine

There total 3 articles about Estramustine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.1%

N,N-bis-(2-chloroethyl)carbamoyl chloride (2998-56-3) + estradiol (50-28-2) → estramustine (2998-57-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 40 ℃; for 4.5h;

Reference yield:

Estromustine (62899-40-5) → estramustine (2998-57-4)

Guidance literature:

With hydrogen; nickel;

DOI:10.1021/jm00314a009

Reference yield:

→ estramustine (2998-57-4)

Guidance literature:

upstream raw materials:

N,N-bis-(2-chloroethyl)carbamoyl chloride

estradiol

Estromustine

Downstream raw materials:

estradiol

Estrone

Refernces

• 1、 -. "ANTICANCER AGENTS". Page/Page column 27; 33. . Retrieved 2021/02/12.
• 2、 Yempala, Thirumal,Babu, Tomer,Karmakar, Subhendu,Nemirovski, Alina,Ishan, Maisaloon,Gandin, Valentina,Gibson, Dan. "Expanding the Arsenal of PtIV Anticancer Agents: Multi-action PtIV Anticancer Agents with Bioactive Ligands Possessing a Hydroxy Functional Group". supporting information. p. 18218 - 18223. Retrieved 2019/11/13.