Perifosine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202220

CAS#: 157716-52-4

Description: Perifosine is an orally active alkyl-phosphocholine compound with potential antineoplastic activity. Targeting cellular membranes, perifosine modulates membrane permeability, membrane lipid composition, phospholipid metabolism, and mitogenic signal transduction, resulting in cell differentiation and inhibition of cell growth. This agent also inhibits the anti-apoptotic mitogen-activated protein kinase (MAPK) pathway and modulates the balance between the MAPK and pro-apoptotic stress-activated protein kinase (SAPK/JNK) pathways, thereby inducing apoptosis. Perifosine has a lower gastrointestinal toxicity profile than the related agent miltefosine.


Price and Availability

Size
Price

20mg
USD 150
500mg
USD 1850
Size
Price

50mg
USD 350
1g
USD 2250
Size
Price

200mg
USD 950

Perifosine, purity > 98%, is in stock. The same day shipping out after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 202220
Name: Perifosine
CAS#: 157716-52-4
Chemical Formula: C25H52NO4P
Exact Mass: 461.3634
Molecular Weight: 461.66
Elemental Analysis: C, 65.04; H, 11.35; N, 3.03; O, 13.86; P, 6.71


Synonym: KRX-0401; KRX 0401; KRX0401; NKA17;NSC639966;NSC 639966;NSC-639966; D 21266; D-21266

IUPAC/Chemical Name: 1,1-dimethylpiperidin-1-ium-4-yl octadecyl phosphate.

InChi Key: SZFPYBIJACMNJV-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H52NO4P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-29-31(27,28)30-25-20-22-26(2,3)23-21-25/h25H,4-24H2,1-3H3

SMILES Code: O=P(OC1CC[N+](C)(C)CC1)([O-])OCCCCCCCCCCCCCCCCCC


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Perifosine is being developed by Keryx Biopharmaceuticals who have licenced it from Æterna Zentaris Inc. In 2010 perifosine has reached phase II. In one phase II trial for metastatic colon cancer perifosine doubled time to progression. In 2011 it was in a phase III trial for colorectal cancer, and another for multiple myeloma. Perifosine has orphan drug status in the U.S. for the treatment of multiple myeloma and neuroblastoma, and for multiple myeloma in the EU. [source: http://en.wikipedia.org/wiki/Perifosine ].
   
   


References

1: Amantini C, Morelli MB, Santoni M, Soriani A, Cardinali C, Farfariello V, Eleuteri AM, Bonfili L, Mozzicafreddo M, Nabissi M, Cascinu S, Santoni G. Sorafenib induces cathepsin B-mediated apoptosis of bladder cancer cells by regulating the Akt/PTEN pathway. The Akt inhibitor, perifosine, enhances the sorafenib-induced cytotoxicity against bladder cancer cells. Oncoscience. 2015 Mar 23;2(4):395-409. eCollection 2015. PubMed PMID: 26097873; PubMed Central PMCID: PMC4468325.

2: Kim MN, Ro SW, Kim DY, Kim DY, Cho KJ, Park JH, Lim HY, Han KH. Efficacy of perifosine alone and in combination with sorafenib in an HrasG12V plus shp53 transgenic mouse model of hepatocellular carcinoma. Cancer Chemother Pharmacol. 2015 Jun 3. [Epub ahead of print] PubMed PMID: 26037205.

3: Testen A, Podlipec R, Mravljak J, Orthmann A, Šentjurc M, Zeisig R, Štrancar J, Koklic T. How perifosine affects liposome-encapsulated drug delivery across a cell barrier. Ther Deliv. 2015 Apr;6(4):423-41. doi: 10.4155/tde.14.127. PubMed PMID: 25996042.

4: Ríos-Marco P, Ríos A, Jiménez-López JM, Carrasco MP, Marco C. Cholesterol homeostasis and autophagic flux in perifosine-treated human hepatoblastoma HepG2 and glioblastoma U-87 MG cell lines. Biochem Pharmacol. 2015 Jul 1;96(1):10-9. doi: 10.1016/j.bcp.2015.04.015. Epub 2015 Apr 28. PubMed PMID: 25934232.

5: Cole DE, Lester-McCully CM, Widemann BC, Warren KE. Plasma and cerebrospinal fluid pharmacokinetics of the Akt inhibitor, perifosine, in a non-human primate model. Cancer Chemother Pharmacol. 2015 May;75(5):923-8. doi: 10.1007/s00280-015-2711-1. Epub 2015 Mar 5. PubMed PMID: 25740692.

6: Zhang J, Hong Y, Shen J. Combination treatment with perifosine and MEK-162 demonstrates synergism against lung cancer cells in vitro and in vivo. Tumour Biol. 2015 Feb 20. [Epub ahead of print] PubMed PMID: 25697899.

7: Guidetti A, Carlo-Stella C, Locatelli SL, Malorni W, Mortarini R, Viviani S, Russo D, Marchianò A, Sorasio R, Dodero A, Farina L, Giordano L, Di Nicola M, Anichini A, Corradini P, Gianni AM. Phase II study of perifosine and sorafenib dual-targeted therapy in patients with relapsed or refractory lymphoproliferative diseases. Clin Cancer Res. 2014 Nov 15;20(22):5641-51. doi: 10.1158/1078-0432.CCR-14-0770. Epub 2014 Sep 19. PubMed PMID: 25239609.

8: Figg WD, Monga M, Headlee D, Shah A, Chau CH, Peer C, Messman R, Elsayed YA, Murgo AJ, Melillo G, Ryan QC, Kalnitskiy M, Senderowicz AM, Hollingshead M, Arbuck SG, Sausville EA. A phase I and pharmacokinetic study of oral perifosine with different loading schedules in patients with refractory neoplasms. Cancer Chemother Pharmacol. 2014 Nov;74(5):955-67. doi: 10.1007/s00280-014-2569-7. Epub 2014 Sep 3. PubMed PMID: 25183650.

9: Tomiyasu H, Goto-Koshino Y, Fujino Y, Ohno K, Tsujimoto H. Antitumour effect and modulation of expression of the ABCB1 gene by perifosine in canine lymphoid tumour cell lines. Vet J. 2014 Jul;201(1):83-90. doi: 10.1016/j.tvjl.2014.04.002. Epub 2014 Apr 13. PubMed PMID: 24881508.

10: Koklic T. Perifosine induced release of contents of trans cell-barrier transport efficient liposomes. Chem Phys Lipids. 2014 Oct;183:50-9. doi: 10.1016/j.chemphyslip.2014.05.006. Epub 2014 May 23. PubMed PMID: 24863642.