Tamoxifen citrate

Base Information

• Chemical Name: Tamoxifen citrate
• CAS No.: 54965-24-1
• Deprecated CAS: 7244-97-5
• Molecular Formula: C26H29NO^.C6H8O7
• Molecular Weight: 563.648
• Hs Code.: 29225090
• European Community (EC) Number: 259-415-2
• NSC Number: 757345,180973
• UNII: 7FRV7310N6
• DSSTox Substance ID: DTXSID8021301
• Wikidata: Q27108378
• NCI Thesaurus Code: C855
• RXCUI: 40137
• Pharos Ligand ID: 77VBQQV883JS
• ChEMBL ID: CHEMBL786
• Mol file: 54965-24-1.mol

Synonyms:Citrate, Tamoxifen;ICI 46,474;ICI 46474;ICI 47699;ICI-46,474;ICI-46474;ICI-47699;ICI46,474;ICI46474;ICI47699;Nolvadex;Novaldex;Soltamox;Tamoxifen;Tamoxifen Citrate;Tomaxithen;Zitazonium

Chemical Property of Tamoxifen citrate

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 140-144 °C
• Boiling Point: 665.9 °C at 760 mmHg
• Flash Point: 356.5 °C
• PSA: 144.60000
• LogP: 4.74760
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive & Hygroscopic
• Solubility.: methanol: soluble50mg/mL, clear, colorless
• Water Solubility.: slightly soluble
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 13
• Exact Mass: 563.25191714
• Heavy Atom Count: 41
• Complexity: 690

Purity/Quality:

99.9% ^*data from raw suppliers

Tamoxifen citrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 45-60-61-22-64-36/37/38
• Safety Statements: 53-36/37/39-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Isomeric SMILES: CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Recent ClinicalTrials: Chemotherapy and Stem Cell Transplantation in Treating Patients With Stage IIIB Breast Cancer
• Recent EU Clinical Trials: A randomized, multicenter, double-blind, Phase 3 study of amcenestrant (SAR439859) versus tamoxifen for the treatment of patients with hormone receptor-positive, human epidermal growth factor receptor 2-negative or positive, stage IIB-III breast cancer who have discontinued adjuvant aromatase inhibitor therapy due to treatment-related toxicity
• Description: Tamoxifen citrate (54965-24-1) is an estrogen receptor antagonist/partial agonist. Induces oxidative stress and apoptosis in estrogen receptor-negative cancer cell lines.1 Displays neuroprotective effects in permanent focal ischemia.2 Inhibits PKC.3 Potent agonist at GPR30 (membrane estrogen receptor).4 Clinically useful breast cancer agent.5
• Uses: estrogen antagonist, antineoplastic anti-estrogen, protein kinase C inhibitor, beneficial cardiovascular effects, bone cancer treatment, induces DNA adduct formation Tamoxifen Citrate is a selective estrogen response modifier (SERM), protein kinase C inhibitor and anti-angiogenetic factor. Tamoxifen is a prodrug that is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2D6 and CYP3A4.
• Therapeutic Function: Antiestrogen, Antineoplastic

Technology Process of Tamoxifen citrate

There total 4 articles about Tamoxifen citrate 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:

1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol (748-97-0,82407-94-1) + citric acid (77-92-9,906507-37-7) → tamoxifen citrate (54965-24-1) + (Z)-2-(4-(1,2-diphenylbut-1-enyl)phenoxy)-N,N-dimethylethylamine citrate (54965-24-1)

Guidance literature:

1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol; With hydrogenchloride; In water; isopropyl alcohol; for 5h; Reflux;

citric acid; In acetone; at -5 - 10 ℃; for 10h;

Reference yield:

1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol (748-97-0,82407-94-1) + citric acid (77-92-9,906507-37-7) → tamoxifen citrate (54965-24-1) + (Z)-2-(4-(1,2-diphenylbut-1-enyl)phenoxy)-N,N-dimethylethylamine citrate (54965-24-1)

Guidance literature:

1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol; With hydrogenchloride; In water; isopropyl alcohol; for 5h; Reflux;

citric acid; In acetone; at -5 - 10 ℃; for 10h;

Reference yield:

tamoxifen (10540-29-1,7728-73-6) + citric acid (77-92-9,906507-37-7) → tamoxifen citrate (54965-24-1)

Guidance literature:

In acetonitrile;

DOI:10.1007/s11095-006-9644-7

upstream raw materials:

tamoxifen

citric acid

1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol

Refernces

• 1、 -. "A tamoxifen E isomer preparation method". Paragraph 0055-0059. . Retrieved 2017/03/08.