Lasofoxifene

Base Information

• Chemical Name: Lasofoxifene
• CAS No.: 180916-16-9
• Molecular Formula: C28H31NO2
• Molecular Weight: 413.56
• UNII: 337G83N988
• DSSTox Substance ID: DTXSID50171037
• Nikkaji Number: J992.677A
• Wikipedia: Lasofoxifene
• Wikidata: Q644675
• NCI Thesaurus Code: C80679
• Pharos Ligand ID: D7PPZ3AWHZ16,D7PTN2C9LXHX
• Metabolomics Workbench ID: 149674
• ChEMBL ID: CHEMBL328190
• Mol file: 180916-16-9.mol

Synonyms:(-)-cis-5,6,7,8-tetrahydro-6-phenyl-5-(p-(2-(1-pyrrolidinyl)ethoxy)phenyl)-2-naphthol;cis-1R-(4'-pyrrolidinoethoxyphenyl)-2S-phenyl-6-hydroxy-1,2,3,4-tetrahydronaphthalene, tartrate salt;CP 336156;CP-336,156;LAS estrogen receptor modulator;Lasofoxifene;lasofoxifene hydrochloride

Chemical Property of Lasofoxifene

Chemical Property:

• Vapor Pressure: 1.05E-13mmHg at 25°C
• Melting Point: 110-113°C
• Refractive Index: 1.613
• Boiling Point: 572.4 °C at 760 mmHg
• PKA: 10.31±0.60(Predicted)
• Flash Point: 300 °C
• PSA: 32.70000
• Density: 1.15 g/cm³
• LogP: 5.66660
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 413.235479232
• Heavy Atom Count: 31
• Complexity: 533

Purity/Quality:

98% ^*data from raw suppliers

Lasofoxifene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)CCOC2=CC=C(C=C2)C3C(CCC4=C3C=CC(=C4)O)C5=CC=CC=C5
• Isomeric SMILES: C1CCN(C1)CCOC2=CC=C(C=C2)[C@H]3[C@H](CCC4=C3C=CC(=C4)O)C5=CC=CC=C5
• Recent ClinicalTrials: Evaluation of Lasofoxifene Versus Fulvestrant in Advanced or Metastatic ER+/HER2- Breast Cancer With an ESR1 Mutation
• Recent EU Clinical Trials: An Open-label, Randomized, Multicenter Study Evaluating the Activity of Lasofoxifene Relative to Fulvestrant for the Treatment of Pre- and Postmenopausal Women with Locally Advanced or Metastatic ER+/HER2? Breast Cancer with an ESR1 Mutation
• Uses: A next-generation selective estrogen receptor modulator for treating disorders associated with increased bone turnover and osteopenia.
• Clinical Use: Lasofoxifene is a very potent second-generation SERM currently in phase III clinical trials for the treatment and prevention of osteoporosis in postmenopausal women.

Technology Process of Lasofoxifene

There total 13 articles about Lasofoxifene 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: 80.0%

1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine (5879-98-1) → lasofoxifene (180916-16-9,180915-78-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -50 - 0 ℃; for 3h;

DOI:10.1080/00397911.2015.1135957

Reference yield: 76.0%

7-methoxylasofoxifene → lasofoxifene (180916-16-9,180915-78-0)

Guidance literature:

7-methoxylasofoxifene; With boron tribromide; In dichloromethane; at -78 - 0 ℃; for 2h;

With water; sodium hydrogencarbonate; In dichloromethane;

Reference yield: 57.0%

1-[2-(4-bromophenoxy)ethyl]pyrrolidine (1081-73-8) + n-BuU + 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9) → lasofoxifene (180916-16-9,180915-78-0)

Guidance literature:

CeCl₃; In tetrahydrofuran; hydrogenchloride; diethyl ether;

upstream raw materials:

lasofoxifene

nafoxidine

1-[2-(4-bromophenoxy)ethyl]pyrrolidine

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Downstream raw materials:

1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine

Lasofoxifene tartrate