Perifosine | CAS#157716-52-4 | AKT inhibitor

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.

Chemical Structure

Perifosine

CAS# 157716-52-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202220
Name: Perifosine
CAS#: 157716-52-4
Chemical Formula: C25H52NO4P
Exact Mass: 461.36
Molecular Weight: 461.660
Elemental Analysis: C, 65.04; H, 11.35; N, 3.03; O, 13.86; P, 6.71

Price and Availability

Size	Price	Availability
10mg	USD 110	Ready to ship
25mg	USD 220	Ready to ship
50mg	USD 400	Ready to ship
100mg	USD 700	Ready to ship
200mg	USD 1250	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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

Appearance: Solid powder

Purity: >96% (or refer to the Certificate of Analysis)

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).

HS Tariff Code: 2934.99.9001

More Info: Perifosine is being developed by Keryx Biopharmaceuticals who have licenced it from Ã†terna 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 ].

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#SSC20709

QC Data:

View QC data: current batch, Lot#SSC20709

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Perifosine is an oral Akt inhibitor which inhibits proliferation of different tumor cell lines with IC50s of 0.6-8.9 μM.
In vitro activity:	Perifosine significantly inhibited RMS (Rhabdomyosarcoma) cell growth in concentration- and time-dependent manners. Meanwhile, perifosine induced dramatic apoptosis in RMS cells. At the signaling level, perifosine blocked AKT activation, while inducing reactive oxygen species (ROS) production as well as JNK and P38 phosphorylations in RMS cells. Reference: Tumour Biol. 2016 Jan;37(1):1025-33. https://link.springer.com/article/10.1007/s13277-015-3740-4
In vivo activity:	Rats pretreated with vehicle or perifosine were monitored for spontaneous seizures from week 1 to week 6 after KA (kainic acid) induced status epilepticus. All the vehicle-treated rats developed spontaneous seizures, with an average of 1.5 ± 0.3 seizures/24 h in week 1 and 3.8 ± 0.5 in week 6. In contrast, the perifosine-pretreated rats had a low frequency of 0.5 ± 0.1 seizures/24 h from week 1 to week 6 (F = 3.124, P < 0.05, Fig. 5B). Reference: Neurosci Bull. 2018 Apr;34(2):283-290. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5856709/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Water	10.0	21.70
	Ethanol	30.0	65.00

Preparing Stock Solutions

The following data is based on the product molecular weight 461.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Shen J, Hong Y, Zhao Q, Zhang JL. Preclinical evaluation of perifosine as a potential promising anti-rhabdomyosarcoma agent. Tumour Biol. 2016 Jan;37(1):1025-33. doi: 10.1007/s13277-015-3740-4. Epub 2015 Aug 13. PMID: 26269112. 2. Li Z, Tan F, Liewehr DJ, Steinberg SM, Thiele CJ. In vitro and in vivo inhibition of neuroblastoma tumor cell growth by AKT inhibitor perifosine. J Natl Cancer Inst. 2010 Jun 2;102(11):758-70. doi: 10.1093/jnci/djq125. Epub 2010 May 12. PMID: 20463309; PMCID: PMC2879416. 3. Zhu F, Kai J, Chen L, Wu M, Dong J, Wang Q, Zeng LH. Akt Inhibitor Perifosine Prevents Epileptogenesis in a Rat Model of Temporal Lobe Epilepsy. Neurosci Bull. 2018 Apr;34(2):283-290. doi: 10.1007/s12264-017-0165-7. Epub 2017 Aug 7. PMID: 28786074; PMCID: PMC5856709.
In vitro protocol:	1. Shen J, Hong Y, Zhao Q, Zhang JL. Preclinical evaluation of perifosine as a potential promising anti-rhabdomyosarcoma agent. Tumour Biol. 2016 Jan;37(1):1025-33. doi: 10.1007/s13277-015-3740-4. Epub 2015 Aug 13. PMID: 26269112. 2. Li Z, Tan F, Liewehr DJ, Steinberg SM, Thiele CJ. In vitro and in vivo inhibition of neuroblastoma tumor cell growth by AKT inhibitor perifosine. J Natl Cancer Inst. 2010 Jun 2;102(11):758-70. doi: 10.1093/jnci/djq125. Epub 2010 May 12. PMID: 20463309; PMCID: PMC2879416.
In vivo protocol:	1. Zhu F, Kai J, Chen L, Wu M, Dong J, Wang Q, Zeng LH. Akt Inhibitor Perifosine Prevents Epileptogenesis in a Rat Model of Temporal Lobe Epilepsy. Neurosci Bull. 2018 Apr;34(2):283-290. doi: 10.1007/s12264-017-0165-7. Epub 2017 Aug 7. PMID: 28786074; PMCID: PMC5856709. 2. Li Z, Tan F, Liewehr DJ, Steinberg SM, Thiele CJ. In vitro and in vivo inhibition of neuroblastoma tumor cell growth by AKT inhibitor perifosine. J Natl Cancer Inst. 2010 Jun 2;102(11):758-70. doi: 10.1093/jnci/djq125. Epub 2010 May 12. PMID: 20463309; PMCID: PMC2879416.

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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.

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