Bazedoxifene

Base Information

• Chemical Name: Bazedoxifene
• CAS No.: 198481-32-2
• Molecular Formula: C30H34N2O3
• Molecular Weight: 470.612
• European Community (EC) Number: 805-732-1
• UNII: Q16TT9C5BK
• DSSTox Substance ID: DTXSID70173593
• Nikkaji Number: J1.561.275D
• Wikipedia: Bazedoxifene
• Wikidata: Q4875166
• NCI Thesaurus Code: C73598
• RXCUI: 1441386
• Pharos Ligand ID: AJ33Z8Z6P4XV
• Metabolomics Workbench ID: 149760
• ChEMBL ID: CHEMBL46740
• Mol file: 198481-32-2.mol

Synonyms:bazedoxifene;bazedoxifene acetate;TSE 424;TSE-424;TSE424;WAY-140424

Chemical Property of Bazedoxifene

Chemical Property:

• Vapor Pressure: 6.33E-20mmHg at 25°C
• Melting Point: 98-102°
• Refractive Index: 1.622
• Boiling Point: 694.4 °C at 760 mmHg
• PKA: 10.12±0.15(Predicted)
• Flash Point: 373.8 °C
• PSA: 57.86000
• Density: 1.19 g/cm³
• LogP: 6.26890
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 470.25694295
• Heavy Atom Count: 35
• Complexity: 623

Purity/Quality:

99%, ^*data from raw suppliers

Bazedoxifene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N(C2=C1C=C(C=C2)O)CC3=CC=C(C=C3)OCCN4CCCCCC4)C5=CC=C(C=C5)O
• Recent ClinicalTrials: A Study of Palbociclib in Combination With Bazedoxifene in Hormone Receptor Positive Breast Cancer
• Recent EU Clinical Trials: A 2-Part, Open-label, Non-randomized (Part A) and Randomized, Double-blinded, Placebo-controlled (Part B) multicentric, international study with adaptive design to evaluate safety and tolerability of bazedoxifene, concentrated solution for nebulization (BAZE-X1) in addition to Standard of Care in hospitalized COVID-19 patients suffering from moderate to severe Pneumonia.
• Recent NIPH Clinical Trials: The effects of bazedoxifene and estradiol on the bone mineral density and bone turnover markers in postmenopausal women
• Uses: Bazedoxifene is an nonsteroidal selective estrogen receptor modulator (SERM). Bazedoxifene is used as an antiosteoporotic.
• Clinical Use: Bazedoxifene is an indole-based SERM that is under investigation for the treatment and prevention of postmenopausal osteoporosis. It also is being evaluated in combination with Premarin (conjugated estrogens). Bazedoxifene displaces 17β-estradiol from estrogen receptors and has excellent binding affinity for the receptor itself. Unlike raloxifene, this agent does not cause hot flashes at the doses required to have a beneficial effect on bone. In addition, it does not cause uterine or mammary gland stimulation.

Technology Process of Bazedoxifene

There total 74 articles about Bazedoxifene 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: 95.0%

1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-5-methoxy-2-(4-methoxy-phenyl)-3-methyl-1H-indole → bazedoxifene (198481-32-2)

Guidance literature:

With trimethylsilyl iodide; In chloroform; at 20 ℃; for 5h;

Reference yield: 89.0%

1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride (223251-25-0) + 4-(5-acetoxy-3-methyl-1H-indol-2-yl)phenyl acetate (91444-55-2) → bazedoxifene (198481-32-2)

Guidance literature:

4-(5-acetoxy-3-methyl-1H-indol-2-yl)phenyl acetate; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 5 ℃; for 2h; Inert atmosphere;

1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 15h;

With sodium hydroxide; In N,N-dimethyl-formamide; at 25 ℃; for 15h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 87.0%

1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-5-(tert-butoxy)-2-(4-(tert-butoxy)phenyl)-3-methyl-1H-indole → bazedoxifene (198481-32-2)

Guidance literature:

With hydrogen bromide; acetic acid; at 20 ℃; for 0.5h;

upstream raw materials:

5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-1H-indole

(4-hydroxyphenyl)methanol

1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone

4-benzyloxyaniline hydrochloride

Downstream raw materials:

bazedoxifene ascorbate

bazedoxifene acetate

1-[4-(2-azepan-1-yl-ethoxy)benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol mesylate

1-[4-(2-azepan-1-yl-ethoxy)benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol propionate

Refernces

• 1、 -. "METHODS OF PREPARINGBAZEDOXIFENE BY NEW INTERMEDIATES". Paragraph 0060; 0076-0079. . Retrieved 2019/12/25.
• 2、 -. "METHODS OF PREPARING　BAZOEDOXIFENE". Paragraph 0095; 0105-0107. . Retrieved 2018/10/16.