Perifosine

Base Information

• Chemical Name: Perifosine
• CAS No.: 157716-52-4
• Molecular Formula: C₂₅H₅₂NO₄P
• Molecular Weight: 461.666
• Hs Code.: 2933399090
• European Community (EC) Number: 690-653-3
• NSC Number: 639966
• UNII: 2GWV496552
• DSSTox Substance ID: DTXSID3048946
• Wikipedia: Perifosine
• Wikidata: Q3411917
• NCI Thesaurus Code: C1727
• Metabolomics Workbench ID: 65020
• ChEMBL ID: CHEMBL372764
• Mol file: 157716-52-4.mol

Synonyms:D 21266;D-21266;octadecyl-(1,1-dimethyl-4-piperidylio)phosphate;perifosine

Chemical Property of Perifosine

Chemical Property:

• Melting Point: 271-272° (dec)
• PSA: 68.40000
• LogP: 8.01730
• Storage Temp.: ?20°C
• Solubility.: H2O: soluble10mg/mL, clear
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 20
• Exact Mass: 461.36339614
• Heavy Atom Count: 31
• Complexity: 454

Purity/Quality:

99% ^*data from raw suppliers

Perifosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCOP(=O)([O-])OC1CC[N+](CC1)(C)C
• Recent ClinicalTrials: Perifosine and Torisel (Temsirolimus) for Recurrent/Progressive Malignant Gliomas
• Recent EU Clinical Trials: A Phase III Randomized Study to Assess the Efficacy and Safety of Perifosine Added to the Combination of Bortezomib and Dexamethasone in Multiple Myeloma
• Recent NIPH Clinical Trials: Phase I/II trial of YHI-1003 plus Capecitabine
• Description: Perifosine (KRX-0401) is a novel Akt inhibitor with IC50 of 4.7 μM in MM.1S cells, targets pleckstrin homology domain of Akt. Phase 3.
• Uses: Antineoplastic. It acts as an Akt inhibitor and a PI3K inhibitor, and is a drug candidate being developed for a variety of cancer indications. An alkylphospholipid which inhibits Akt activation and the anti-apoptotic MAPK pathway.

Technology Process of Perifosine

There total 2 articles about Perifosine 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: 16.0%

4-hydroxy-1,1-dimethylpiperidinium p-toluenesulphonate + 1-octadecanol (112-92-5) → perifosine (157716-52-4)

Guidance literature:

1-octadecanol; With triethylamine; trichlorophosphate; In diethyl ether; at 0 - 20 ℃; for 16h;

4-hydroxy-1,1-dimethylpiperidinium p-toluenesulphonate; With dmap; triethylamine; In chloroform; at 20 ℃; for 48h;

With water; In tetrahydrofuran; for 6h; Reflux;

DOI:10.1007/s11095-020-02830-y

Reference yield:

→ perifosine (157716-52-4)

Guidance literature:

upstream raw materials:

1-octadecanol

Refernces

• 1、 -. "Novel alkyl phospholipid derivatives and uses thereof". Page/Page column 60. . Retrieved 2010/11/27.