Perifosine

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Perifosine
Skeletal formula of perifosine
Space-filling model of the perifosine zwitterion
Names
IUPAC name
1,1-Dimethylpiperidinium-4-yl octadecyl phosphate
Other names
D 21266; KRX 0401
Identifiers
157716-52-4 YesY
ChEMBL ChEMBL372764
ChemSpider 130628
7424
Jmol 3D model Interactive image
PubChem 148177
UNII 2GWV496552 YesY
  • 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
  • [O-]P(=O)(OCCCCCCCCCCCCCCCCCC)OC1CC[N+](C)(C)CC1
Properties
C25H52NO4P
Molar mass 461.67 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Perifosine (also KRX-0401) is a drug candidate being developed for a variety of cancer indications. It is an alkyl-phospholipid[1] structurally related to miltefosine. It acts as an Akt inhibitor and a PI3K inhibitor. It was being developed by Keryx Biopharmaceuticals who have licensed it from Æterna Zentaris Inc.[2]

In 2010 perifosine has reached phase II.[3] In one phase II trial for metastatic colon cancer perifosine doubled time to progression.[2]

It has orphan drug status in the U.S. for the treatment of multiple myeloma and neuroblastoma, and for multiple myeloma in the EU.[4]

In 2011 it was in a phase III trial for colorectal cancer,[5] and another for multiple myeloma.[4][6] On April 2, 2012, it was announced that perifosine failed its phase III clinical trial for treatment of colon cancer.[7] Detailed results were released in June 2012.[8] On March 11, 2013 Aeterna Zentaris announced the discontinuing of Phase 3 clinical trial of perifosine for the treatment of relapsed and refractory multiple myeloma http://www.aezsinc.com/en/page.php?p=60&q=550.

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Smartoncology newsletter, Feb 2010
  3. ↑ June 7, 2010: Presentation at the American Society of Clinical Oncology annual meeting of Phase I data on single agent perifosine in the treatment of recurrent pediatric solid tumors, including patients with advanced brain tumors and neuroblastoma. also Phase II trial of the novel oral Akt inhibitor perifosine in relapsed and/or refractory Waldenstrom macroglobulinemia (WM).
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ http://www.clinicaltrial.gov/ct2/show/NCT01097018
  6. ↑ http://www.clinicaltrial.gov/ct2/show/NCT01002248
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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