Toremifene

Base Information

• Chemical Name: Toremifene
• CAS No.: 89778-26-7
• Deprecated CAS: 98644-21-4
• Molecular Formula: C26H28ClNO
• Molecular Weight: 405.967
• Hs Code.: 2922299090
• European Community (EC) Number: 618-298-1
• UNII: 7NFE54O27T
• DSSTox Substance ID: DTXSID3023689
• Nikkaji Number: J745.747B,J33.157K
• Wikipedia: Toremifene
• Wikidata: Q3993743
• NCI Thesaurus Code: C1256
• RXCUI: 38409
• Pharos Ligand ID: 1LDXY56K79J2
• Metabolomics Workbench ID: 42876
• ChEMBL ID: CHEMBL1655
• Mol file: 89778-26-7.mol

Synonyms:Citrate, Toremifene;Fareston;FC 1157a;FC-1157a;FC1157a;Toremifene;Toremifene Citrate;Toremifene Citrate (1:1);Toremifene, (E)-Isomer

Chemical Property of Toremifene

Chemical Property:

• Appearance/Colour: White-to-Off-White Solid
• Vapor Pressure: 1.58E-11mmHg at 25°C
• Melting Point: 108-110°C
• Boiling Point: 535.1 °C at 760 mmHg
• PKA: 8.69±0.28(Predicted)
• Flash Point: 277.4 °C
• PSA: 12.47000
• Density: 1.104 g/cm³
• LogP: 6.21500
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 405.1859422
• Heavy Atom Count: 29
• Complexity: 483

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

Toremifene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: CN(C)CCOC1=CC=C(C=C1)/C(=C(/CCCl)\C2=CC=CC=C2)/C3=CC=CC=C3
• Recent ClinicalTrials: 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
• Recent EU Clinical Trials: ARTEST - A Randomized Phase 3 Study to Evaluate the Efficacy and Safety of Enobosarm Monotherapy Versus Active Control for the Treatment of AR+/ER+/HER2- Metastatic Breast Cancer in Patients with Androgen Receptor Nuclei Staining ≥40% Who Have Shown Previous Disease Progression on a Nonsteroidal Aromatase Inhibitor, Fulvestrant and CDK 4/6 inhibitor
• Recent NIPH Clinical Trials: Randomized Comparative Trial of High-dose FARESTON for Aromatase Inhibitor resistant breast cancer compared to Faslodex
• Description: Toremifene is an antiestrogenic anticancer agent effective in the treatment of advanced recurrent breast cancer in postmenopausal patients. It is claimed to be more effective than tamoxifen in several rat mammary tumor models. Side-effects are mild, including hot flushes and sweating.
• Uses: An antiestrogen and antineoplastic. Nonsteroidal antiestrogen structurally similar to tamoxifen antineoplastic;selective estrogen receptor modulator A chlorinated tamoxifen analogue, that induces apoptosis in some cells
• Clinical Use: Hormone dependent metastatic breast cancer in post menopausal women
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: enhanced anticoagulant effect of coumarins. Cytotoxics: possible increased risk of ventricular arrhythmias with vandetanib - avoid.

Technology Process of Toremifene

There total 6 articles about Toremifene 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: 40.0%

1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]butane-1,4-diol (141854-25-3) → toremifene (89778-26-7)

Guidance literature:

1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]butane-1,4-diol; With thionyl chloride; In toluene; at -10 - 80 ℃; for 12 - 14h;

With sodium hydroxide; In water; toluene; at 45 - 55 ℃;

Reference yield:

4-hydroxy-1,2-diphenyl-1-[4-[2-N,N-dimethylamino]ethoxy]-phenyl-1-butene (1262682-37-0) → toremifene (89778-26-7)

Guidance literature:

4-hydroxy-1,2-diphenyl-1-[4-[2-N,N-dimethylamino]ethoxy]-phenyl-1-butene; With thionyl chloride; In dichloromethane; at 20 - 42 ℃; for 7h;

With ammonia; In water; ethyl acetate; pH=8.1 - 8.3;

Reference yield:

(Z)-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-buten-4-ol (97151-03-6) → toremifene (89778-26-7)

Guidance literature:

With thionyl chloride; In toluene; at 0 - 110 ℃; for 3h; Temperature;

upstream raw materials:

1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]butane-1,4-diol

4-hydroxy-1,2-diphenyl-1-[4-[2-N,N-dimethylamino]ethoxy]-phenyl-1-butene

4-Hydroxybenzophenone

3-hydroxy-1-phenylpropan-1-one

Downstream raw materials:

toremifene citrate

Refernces

• 1、 -. "POLYMORPHIC FORM OF TOREMIFENE CITRATE AND PROCESS FOR ITS PREPARATION". Page/Page column 14. . Retrieved 2011/02/24.