Ospemifene

Base Information

• Chemical Name: Ospemifene
• CAS No.: 128607-22-7
• Molecular Formula: C24H23 Cl O2
• Molecular Weight: 378.898
• European Community (EC) Number: 664-452-6
• UNII: B0P231ILBK
• DSSTox Substance ID: DTXSID101025426
• Nikkaji Number: J385.176A,J501.141H
• Wikipedia: Ospemifene
• Wikidata: Q7107372
• NCI Thesaurus Code: C76958
• RXCUI: 1370971
• Pharos Ligand ID: NT8WQY86H2HD
• Metabolomics Workbench ID: 66337
• ChEMBL ID: CHEMBL2105395
• Mol file: 128607-22-7.mol

Synonyms:FC-1271a;Ospemifene;Osphena;Senshio;Z-2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

Chemical Property of Ospemifene

Chemical Property:

• Vapor Pressure: 1.08E-12mmHg at 25°C
• Boiling Point: 544.6°C at 760 mmHg
• PKA: 14.26±0.10(Predicted)
• Flash Point: 283.2°C
• PSA: 29.46000
• Density: 1.166g/cm³
• LogP: 5.64570
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 378.1386577
• Heavy Atom Count: 27
• Complexity: 441

Purity/Quality:

99.9% ^*data from raw suppliers

Ospemifene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C3=CC=C(C=C3)OCCO)CCCl
• Isomeric SMILES: C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C3=CC=C(C=C3)OCCO)/CCCl
• Recent ClinicalTrials: Effects of Ospemifene on Brain Activation Patterns in Women With Sexual Interest-arousal Disorders
• Recent EU Clinical Trials: Efficacy and Long-Term Safety of Ospemifene in the Treatment of Vulvar and Vaginal Atrophy (VVA) in Postmenopausal Women: A 52-Week, Randomized, Double-Blind, Placebo-Controlled, Parallel-Group Study Comparing 60 mg Oral Daily Dose of Ospemifene with Placebo
• Description: In February 2013, the US FDA approved ospemifene (also referred to as FC1271a), for the treatment ofmoderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy (VVA), due tomenopause. It is estimated that there are 150 million postmenopausal women worldwide with 40–70% suffering from VVA. Ospemifene is a selective estrogen receptor (ER) modulator (SERM) and the first nonhormonal, nonestrogen for the treatment of moderate to severe dyspareunia in women with menopausal VVA. It binds to ERα (IC50～800 nM) and ERβ (IC50～1600 nM) with tissue-specific estrogenic agonist/antagonist effects. Treatment with ospemifene increases the thickness of the vaginal tissue thereby decreasing fragility of the tissue and reducing potential for pain during sexual intercourse.
• Uses: Treatment of vaginal atrophy, osteoporosis, and vasomotor symptoms.
• Clinical Use: Ospemifene is a SERM that is currently in Phase II/III clinical trials for the treatment of postmenopausal osteoporosis and urogenital atrophy. It is a known metabolite of toremifene, a triphenylethylene derivative used to treat breast cancer.Ospemifene has been shown to have beneficial effects on the bone without significant estrogen-related side effects. The beneficial effect observed on bone stems from this agent's ability to increase osteoblast proliferation and, as a result, to enhance bone mineralization as well as bone formation. Unlike tamoxifen, ospemifene does not induce osteocyte apoptosis.

Technology Process of Ospemifene

There total 27 articles about Ospemifene 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: 96.0%

3-chloropropiophenone (936-59-4) + (4-(2-hydroxyethoxy)phenyl)(phenyl)methanone (14814-17-6) → ospemifene (128607-22-7)

Guidance literature:

With titanium tetrachloride; zinc; In 2-methyltetrahydrofuran; at 15 - 50 ℃; Product distribution / selectivity;

Reference yield: 59.0%

(Z)-4-(4-chloro-1,2-diphenylbut-1-enyl)phenol (89778-41-6) + 2-tetrahydropyranyloxy-1-iodoethane (96388-83-9) → ospemifene (128607-22-7)

Guidance literature:

(Z)-4-(4-chloro-1,2-diphenylbut-1-enyl)phenol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

2-tetrahydropyranyloxy-1-iodoethane; In tetrahydrofuran; for 9h; Heating / reflux;

With hydrogenchloride; water; In ethanol; at 20 ℃; Product distribution / selectivity;

Reference yield: 45.0%

(Z)-2-(4-(4-chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethyl benzoate (1602487-47-7) → ospemifene (128607-22-7)

Guidance literature:

With lithium aluminium tetrahydride; In toluene; at 23 ℃; for 0.5h; Inert atmosphere;

upstream raw materials:

(Z)-(1-(4-(2-(benzyloxy)ethoxy)phenyl)-4-chlorobut-1-ene-1,2-diyl)dibenzene

(Z)-4-(4-chloro-1,2-diphenylbut-1-enyl)phenol

2-tetrahydropyranyloxy-1-iodoethane

(Z)-[4-(4-Chloro-1,2-diphenylbut-1-enyl]phenoxy)acetic Acid Ethyl Ester

Refernces

• 1、 Kumar, Sumit,Palma, Gabriella,Perumal, Shanen,Kaur, Mandeep,Singh-Pillay, Ashona,Raj, Raghu,Singh, Parvesh,Kumar, Vipan. "Triarylethylene-indolin-2,3-dione molecular conjugates: Design, synthesis, docking studies and anti-proliferation evaluation". . p. 42409 - 42414. Retrieved 2019.
• 2、 -. "Polymorphic forms of the formulations (by machine translation)". Paragraph 0041; 0042; 0043. . Retrieved 2017/04/07.