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MedKoo Cat#: 202220 | Name: Perifosine
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Description:

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

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
Perifosine
CAS#157716-52-4

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

Price and Availability

Size Price Availability Quantity
10mg USD 110.00 Ready to ship
25mg USD 220.00 Ready to ship
50mg USD 400.00 Ready to ship
100mg USD 700.00 Ready to ship
200mg USD 1,250.00 Ready to ship
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Related CAS #
No Data
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 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 ].        
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/
Solvent mg/mL mM
Solubility
Water 10.0 21.70
Ethanol 30.0 65.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

Recalculate based on batch purity %
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.
1: Correction to: In Vitro and In Vivo Inhibition of Neuroblastoma Tumor Cell Growth by AKT Inhibitor Perifosine. J Natl Cancer Inst. 2024 Aug 1;116(8):1406. doi: 10.1093/jnci/djae167. Erratum for: J Natl Cancer Inst. 2010 Jun 2;102(11):758-70. doi: 10.1093/jnci/djq125. PMID: 38994894. 2: Zhao W, Zhou L, Zhao W, Yang H, Lu Z, Zhang L, Zhang Y, Xie Y, Lu H, Han W, He J, Qiu X, Jia F, Zhao W, Zhang B, Wang Z. The combination of temozolomide and perifosine synergistically inhibit glioblastoma by impeding DNA repair and inducing apoptosis. Cell Death Discov. 2024 Jul 8;10(1):315. doi: 10.1038/s41420-024-02085-1. PMID: 38977680; PMCID: PMC11231210. 3: Hossain MA. Targeting the RAS upstream and downstream signaling pathway for cancer treatment. Eur J Pharmacol. 2024 Jun 10;979:176727. doi: 10.1016/j.ejphar.2024.176727. Epub ahead of print. PMID: 38866361. 4: Wu M, Li C, Zhou X, Wu Z, Feng J, Guo X, Fang R, Lian Q, Pan M, Lai X, Peng Y. Wogonin preconditioning of MSCs improved their therapeutic efficiency for colitis through promoting glycolysis. Inflammopharmacology. 2024 Aug;32(4):2575-2587. doi: 10.1007/s10787-024-01491-2. Epub 2024 May 16. PMID: 38753221. 5: Zhou L, Zhao H, Zhang C, Chen Z, Li D, Qian G. Study on the mechanism of CXCL12/CXCR4-axis-mediated upregulation of IL-8 and IL-6 on the biological function of acute T lymphocyte leukaemia cells. Cytotechnology. 2024 Feb;76(1):97-111. doi: 10.1007/s10616-023-00600-3. Epub 2023 Oct 28. PMID: 38304623; PMCID: PMC10828134. 6: Yang Y, Yu L, Zhu T, Xu S, He J, Mao N, Liu Z, Wang D. Neuroprotective effects of Rehmannia glutinosa polysaccharide on chronic constant light (CCL)-induced oxidative stress and autophagic cell death via the AKT/mTOR pathway in mouse hippocampus and HT-22 cells. Int J Biol Macromol. 2024 Mar;261(Pt 2):129813. doi: 10.1016/j.ijbiomac.2024.129813. Epub 2024 Jan 28. PMID: 38286367. 7: Lin X, Wang W, Chang X, Chen C, Guo Z, Yu G, Shao W, Wu S, Zhang Q, Zheng F, Li H. ROS/mtROS promotes TNTs formation via the PI3K/AKT/mTOR pathway to protect against mitochondrial damages in glial cells induced by engineered nanomaterials. Part Fibre Toxicol. 2024 Jan 15;21(1):1. doi: 10.1186/s12989-024-00562-0. PMID: 38225661; PMCID: PMC10789074. 8: Torrens-Mas M, Collado-Solé A, Sola-Leyva A, Carrasco-Jiménez MP, Oliver J, Pons DG, Roca P, Sastre-Serra J. Mitochondrial Functionality Is Regulated by Alkylphospholipids in Human Colon Cancer Cells. Biology (Basel). 2023 Nov 22;12(12):1457. doi: 10.3390/biology12121457. PMID: 38132283; PMCID: PMC10740929. 9: Kang SC, Sarn NB, Venegas J, Tan Z, Hitomi M, Eng C. Germline PTEN genotype- dependent phenotypic divergence during the early neural developmental process of forebrain organoids. Mol Psychiatry. 2023 Nov 29. doi: 10.1038/s41380-023-02325-3. Epub ahead of print. PMID: 38030818. 10: Liu Y, Zhang X, Zhang P, He T, Zhang W, Ma D, Li P, Chen J. A high- throughput Gaussia luciferase reporter assay for screening potential gasdermin E activators against pancreatic cancer. Acta Pharm Sin B. 2023 Oct;13(10):4253-4272. doi: 10.1016/j.apsb.2023.07.018. Epub 2023 Jul 20. PMID: 37799380; PMCID: PMC10548051. 11: Hasan GM, Hassan MI, Sohal SS, Shamsi A, Alam M. Therapeutic Targeting of Regulated Signaling Pathways of Non-Small Cell Lung Carcinoma. ACS Omega. 2023 Jul 17;8(30):26685-26698. doi: 10.1021/acsomega.3c02424. PMID: 37546685; PMCID: PMC10398694. 12: Gama SM, Varela VA, Ribeiro NM, Bizzarro B, Hernandes C, Aloia TPA, Amano MT, Pereira WO. AKT inhibition interferes with the expression of immune checkpoint proteins and increases NK-induced killing of HL60-AML cells. Einstein (Sao Paulo). 2023 Jun 19;21:eAO0171. doi: 10.31744/einstein_journal/2023AO0171. PMID: 37341216; PMCID: PMC10247281. 13: Yin X, Xu Z, Zhang X, Wu J, Lu W. Deficiency of lipopolysaccharide binding protein facilitates adipose browning, glucose uptake and oxygen consumption in mouse embryonic fibroblasts via activating PI3K/Akt/mTOR pathway and inhibiting autophagy. Cell Cycle. 2023 Apr;22(8):967-985. doi: 10.1080/15384101.2023.2169521. Epub 2023 Jan 29. PMID: 36710409; PMCID: PMC10054173. 14: Jin J, Xu F, Zhang Y, Guan J, Fu J. Myocardial ischemia-reperfusion injury is probably due to the excessive production of mitochondrial ROS caused by the activation of 5-HT degradation system mediated by PAF receptor. Mol Immunol. 2023 Mar;155:27-43. doi: 10.1016/j.molimm.2023.01.004. Epub 2023 Jan 20. PMID: 36682136. 15: Holz C, Lange S, Sekora A, Knuebel G, Krohn S, Murua Escobar H, Junghanss C, Richter A. Combined BCL-2 and PI3K/AKT Pathway Inhibition in KMT2A-Rearranged Acute B-Lymphoblastic Leukemia Cells. Int J Mol Sci. 2023 Jan 10;24(2):1359. doi: 10.3390/ijms24021359. PMID: 36674872; PMCID: PMC9865387. 16: Adamová B, Říhová K, Pokludová J, Beneš P, Šmarda J, Navrátilová J. Synergistic cytotoxicity of perifosine and ABT-737 to colon cancer cells. J Cell Mol Med. 2023 Jan;27(1):76-88. doi: 10.1111/jcmm.17636. Epub 2022 Dec 15. PMID: 36523175; PMCID: PMC9806293. 17: Gong B, Zhang J, Hua Z, Liu Z, Thiele CJ, Li Z. Corrigendum: Downregulation of ATXN3 enhances the sensitivity to AKT inhibitors (Perifosine or MK-2206), but decreases the sensitivity to chemotherapeutic drugs (etoposide or cisplatin) in neuroblastoma cells. Front Oncol. 2022 Aug 3;12:984514. doi: 10.3389/fonc.2022.984514. Erratum for: Front Oncol. 2021 Jul 12;11:686898. doi: 10.3389/fonc.2021.686898. PMID: 35992874; PMCID: PMC9382292. 18: Toson B, Fortes IS, Roesler R, Andrade SF. Targeting Akt/PKB in pediatric tumors: A review from preclinical to clinical trials. Pharmacol Res. 2022 Sep;183:106403. doi: 10.1016/j.phrs.2022.106403. Epub 2022 Aug 18. PMID: 35987481. 19: Tong Z, Li G, Su C, Zhou L, Zhang L, Chen Q, Xia Q. L-Borneol 7-O-[β-D-Apiofuranosyl-(1→6)]-β-D-Glucopyranoside Alleviates Myocardial Ischemia-Reperfusion Injury in Rats and Hypoxic/Reoxygenated Injured Myocardial Cells via Regulating the PI3K/AKT/mTOR Signaling Pathway. J Immunol Res. 2022 May 12;2022:5758303. doi: 10.1155/2022/5758303. PMID: 35600046; PMCID: PMC9119761. 20: She PF, Xu LL, Liu YQ, Li ZH, Liu SS, Li YM, Zhou LY, Wu Y. [Perifosine inhibits biofilm formation of Pseudomonas aeruginosa by interacting with PqsE protein]. Zhonghua Yu Fang Yi Xue Za Zhi. 2022 Feb 6;56(2):192-196. Chinese. doi: 10.3760/cma.j.cn112150-20211020-00970. PMID: 35184449.

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