Raloxifene

Base Information

• Chemical Name: Raloxifene
• CAS No.: 84449-90-1
• Molecular Formula: C28H27NO4S
• Molecular Weight: 473.593
• Hs Code.: 29349990
• European Community (EC) Number: 686-786-1
• NSC Number: 747974
• UNII: YX9162EO3I
• DSSTox Substance ID: DTXSID3023550
• Nikkaji Number: J22.982B
• Wikipedia: Raloxifene
• Wikidata: Q425223
• NCI Thesaurus Code: C1518
• RXCUI: 72143
• Pharos Ligand ID: Z21APBSNPM3W
• Metabolomics Workbench ID: 42827
• ChEMBL ID: CHEMBL81
• Mol file: 84449-90-1.mol

Synonyms:Evista;Keoxifene;Keoxifene Hydrochloride;LY 139481;LY 156758;LY-139481;LY-156758;LY139481;LY156758;Raloxifene;Raloxifene HCl;Raloxifene Hydrochloride

Chemical Property of Raloxifene

Chemical Property:

• Appearance/Colour: light-yellow solid
• Melting Point: 250-253 °C
• Boiling Point: 728.2 °C at 760 mmHg
• PKA: 8.83±0.15(Predicted)
• Flash Point: 394.2 °C
• PSA: 98.24000
• Density: 1.289 g/cm³
• LogP: 6.01310
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: 28 mg/mL, soluble
• Water Solubility.: 560μg/L at 25℃
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 473.16607952
• Heavy Atom Count: 34
• Complexity: 655

Purity/Quality:

99% ^*data from raw suppliers

Raloxifene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O)C5=CC=C(C=C5)O
• Recent ClinicalTrials: Comparative Antiresorptive Efficacy Discontinuation of Denosumab
• Recent EU Clinical Trials: Prospective study to evaluate the effects of Raloxifene therapy on SARS-CoV-2 immunity after COVID-19 vaccination
• Recent NIPH Clinical Trials: Impact of raloxifene, eldecalcitol and their combination therapy on bone indices in postmenopausal subjects with osteoporosis and chronic kidney disease stage 3: Re Bone Study
• Uses: A nonsteroidal estrogen receptor mixed agonist/antagonist Raloxifene is a nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic.
• Indications: Raloxifene (Evista) is a new SERM approved for use in the treatment and prevention of osteoporosis because it has estrogenic activity in bone. Raloxifene is an estrogen antagonist in both breast and endometrial tissues. The estrogenlike properties of raloxifene result in the maintenance of a favorable serum lipid profile (decreased low-density lipoprotein levels with no change in either high-density lipoproteins or triglycerides). Raloxifene is 95% bound to plasma proteins. Absorption of raloxifene is impaired by cholestyramine.
• Clinical Use: Raloxifene, the first SERM approved for the prevention of osteoporosis in postmenopausal women, acts as an estrogen agonist on receptors in osteoblasts and osteoclasts but as an antagonist at breast and uterine estrogen receptors.

Technology Process of Raloxifene

There total 39 articles about Raloxifene 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: 100.0%

raloxifene hydrochloride (82640-04-8) → Raloxifen (84449-90-1)

Guidance literature:

raloxifene hydrochloride; With sodium hydroxide; In water; acetone; at 20 ℃;

With acetic acid; In water; acetone; at 16 - 20 ℃; for 1.75h; pH=8;

Reference yield: 100.0%

1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide (1293408-87-3) → Raloxifen (84449-90-1)

Guidance literature:

1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide; With sodium hydroxide; In water; acetone; at 20 ℃;

With acetic acid; In water; acetone; at 12 ℃; for 1h; pH=8 - 9;

Reference yield: 90.0%

[6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-Piperidinyl)ethoxy]phenyl] Methanone (84541-38-8) → Raloxifen (84449-90-1)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 50 ℃;

DOI:10.1080/00397911.2014.943348

upstream raw materials:

<6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride

1-piperidinoethanol

[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl] [4-fluorophenyl]methanone

[6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-Piperidinyl)ethoxy]phenyl] Methanone

Downstream raw materials:

2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-6-hydroxybenzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl ketone

1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide

(6-((tert-butyldimethylsilyl)oxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone

raloxifene-6-glucuronide

Refernces

• 1、 -. "Sulfoxide compound and method of producing benzothiophene derivatives using the same". Page/Page column 17. . Retrieved 2017/09/26.
• 2、 Yang, Yewei,Zhang, Tao,Huang, Wenhai,Shen, Zhenrong. "Piperidine nucleophilic substitution without solvent: An efficient synthesis of raloxifene". . p. 3271 - 3276. Retrieved 2015/10/06.