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Perifosine

CAS No.:
157716-52-4
Catalog Number:
AG001PNU
Molecular Formula:
C25H52NO4P
Molecular Weight:
461.6584
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%
1 week
United States
$157
- +
10mg
98%
1 week
United States
$190
- +
25mg
95%
1 week
United States
$456
- +
50mg
98%
1 week
United States
$515
- +
100mg
98%
1 week
United States
$790
- +
Product Description
Catalog Number:
AG001PNU
Chemical Name:
Perifosine
CAS Number:
157716-52-4
Molecular Formula:
C25H52NO4P
Molecular Weight:
461.6584
MDL Number:
MFCD00927554
IUPAC Name:
(1,1-dimethylpiperidin-1-ium-4-yl) octadecyl phosphate
InChI:
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
InChI Key:
SZFPYBIJACMNJV-UHFFFAOYSA-N
SMILES:
CCCCCCCCCCCCCCCCCCOP(=O)(OC1CC[N+](CC1)(C)C)[O-]
UNII:
2GWV496552
NSC Number:
639966
Properties
Complexity:
454  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
461.363g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
461.668g/mol
Monoisotopic Mass:
461.363g/mol
Rotatable Bond Count:
20  
Topological Polar Surface Area:
58.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
8.3  
Literature
Title Journal
Arsenic trioxide potentiates the anti-cancer activities of sorafenib against hepatocellular carcinoma by inhibiting Akt activation. Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine 20150401
Identification of potent Yes1 kinase inhibitors using a library screening approach. Bioorganic & medicinal chemistry letters 20130801
Perifosine sensitizes curcumin-induced anti-colorectal cancer effects by targeting multiple signaling pathways both in vivo and in vitro. International journal of cancer 20121201
Linker for activation of T-cell family member2 (LAT2) a lipid raft adaptor protein for AKT signaling, is an early mediator of alkylphospholipid anti-leukemic activity. Molecular & cellular proteomics : MCP 20121201
NVP-BEZ235 alone and in combination in mantle cell lymphoma: an effective therapeutic strategy. Expert opinion on investigational drugs 20121101
Inhibition of the AKT/mTOR and erbB pathways by gefitinib, perifosine and analogs of gonadotropin-releasing hormone I and II to overcome tamoxifen resistance in breast cancer cells. International journal of oncology 20121101
Perifosine sensitizes UVB-induced apoptosis in skin cells: new implication of skin cancer prevention? Cellular signalling 20120901
Perifosine enhances mTORC1-targeted cancer therapy by activation of GSK3β in NSCLC cells. Cancer biology & therapy 20120901
In vitro effects of perifosine, bortezomib and lenalidomide against hematopoietic progenitor cells from healthy donors. Investigational new drugs 20120801
Perifosine plus lenalidomide and dexamethasone in relapsed and relapsed/refractory multiple myeloma: a Phase I Multiple Myeloma Research Consortium study. British journal of haematology 20120801
Perifosine plus docetaxel in patients with platinum and taxane resistant or refractory high-grade epithelial ovarian cancer. Gynecologic oncology 20120701
Interleukin-6, osteopontin and Raf/MEK/ERK signaling modulate the sensitivity of human myeloma cells to alkylphosphocholines. Leukemia research 20120601
Perifosine-mediated Akt inhibition in neuroendocrine tumor cells: role of specific Akt isoforms. Endocrine-related cancer 20120601
Perifosine , an oral, anti-cancer agent and inhibitor of the Akt pathway: mechanistic actions, pharmacodynamics, pharmacokinetics, and clinical activity. Expert opinion on drug metabolism & toxicology 20120501
In vitro cytotoxicity of the novel antimyeloma agents perifosine, bortezomib and lenalidomide against different cell lines. Investigational new drugs 20120401
Perifosine induces protective autophagy and upregulation of ATG5 in human chronic myelogenous leukemia cells in vitro. Acta pharmacologica Sinica 20120401
Repression of mammosphere formation of human breast cancer cells by soy isoflavone genistein and blueberry polyphenolic acids suggests diet-mediated targeting of cancer stem-like/progenitor cells. Carcinogenesis 20120301
The Akt inhibitor MK2206 synergizes, but perifosine antagonizes, the BRAF(V600E) inhibitor PLX4032 and the MEK1/2 inhibitor AZD6244 in the inhibition of thyroid cancer cells. The Journal of clinical endocrinology and metabolism 20120201
Metabolic consequences of treatment with AKT inhibitor perifosine in breast cancer cells. NMR in biomedicine 20120201
Evaluating rational non-cross-resistant combination therapy in advanced clear cell renal cell carcinoma: combined mTOR and AKT inhibitor therapy. Cancer chemotherapy and pharmacology 20120101
Synthesis and biological evaluation of cyclopentane-linked alkyl phosphocholines as potential anticancer agents that act by inhibiting Akt phosphorylation. European journal of medicinal chemistry 20120101
Perifosine downregulates MDR1 gene expression and reverses multidrug-resistant phenotype by inhibiting PI3K/Akt/NF-κB signaling pathway in a human breast cancer cell line. Neoplasma 20120101
Induction of sodium/iodide symporter (NIS) expression and radioiodine uptake in non-thyroid cancer cells. PloS one 20120101
Lysolipid containing liposomes for transendothelial drug delivery. BMC research notes 20120101
Perifosine as a potential novel anti-cancer agent inhibits EGFR/MET-AKT axis in malignant pleural mesothelioma. PloS one 20120101
Perifosine-induced inhibition of Akt attenuates brain-derived neurotrophic factor/TrkB-induced chemoresistance in neuroblastoma in vivo. Cancer 20111201
Randomized placebo-controlled phase II trial of perifosine plus capecitabine as second- or third-line therapy in patients with metastatic colorectal cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20111120
Perifosine plus bortezomib and dexamethasone in patients with relapsed/refractory multiple myeloma previously treated with bortezomib: results of a multicenter phase I/II trial. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20111110
Co-administration of perifosine with paclitaxel synergistically induces apoptosis in ovarian cancer cells: more than just AKT inhibition. Cancer letters 20111101
IKBKE protein activates Akt independent of phosphatidylinositol 3-kinase/PDK1/mTORC2 and the pleckstrin homology domain to sustain malignant transformation. The Journal of biological chemistry 20111028
CD81 is essential for the re-entry of hematopoietic stem cells to quiescence following stress-induced proliferation via deactivation of the Akt pathway. PLoS biology 20110901
Perifosine selectively induces cell cycle block and modulates retinoblastoma and E2F1 protein levels in p53 mutated leukemic cell lines. Investigational new drugs 20110401
Induction of programmed cell death by inhibition of AKT with the alkylphosphocholine perifosine in in vitro models of platinum sensitive and resistant ovarian cancers. Archives of gynecology and obstetrics 20110301
Perifosine and CCI 779 co-operate to induce cell death and decrease proliferation in PTEN-intact and PTEN-deficient PDGF-driven murine glioblastoma. PloS one 20110101
Fractionated radiation therapy can induce a molecular profile for therapeutic targeting. Radiation research 20101001
CDC50A plays a key role in the uptake of the anticancer drug perifosine in human carcinoma cells. Biochemical pharmacology 20100915
Dual inhibition of PI3K and mTOR inhibits autocrine and paracrine proliferative loops in PI3K/Akt/mTOR-addicted lymphomas. Blood 20100603
Getting into the AKT. Journal of the National Cancer Institute 20100602
In vitro and in vivo inhibition of neuroblastoma tumor cell growth by AKT inhibitor perifosine. Journal of the National Cancer Institute 20100602
Computational screening for membrane-directed inhibitors of mast cell activation. European journal of medicinal chemistry 20100601
Antiproliferative effects of antiestrogens and inhibitors of growth factor receptor signaling on endometrial cancer cells. Anticancer research 20100601
Inhibition of pulmonary metastasis in a human MT3 breast cancer xenograft model by dual liposomes preventing intravasal fibrin clot formation. Breast cancer research and treatment 20100501
Perifosine-related rapidly progressive corneal ring infiltrate. Cornea 20100501
[Waldenström's macroglobulinemia]. La Revue de medecine interne 20100501
Disruption of cellular cholesterol transport and homeostasis as a novel mechanism of action of membrane-targeted alkylphospholipid analogues. British journal of pharmacology 20100501
Dual inhibition of akt/mammalian target of rapamycin pathway by nanoparticle albumin-bound-rapamycin and perifosine induces antitumor activity in multiple myeloma. Molecular cancer therapeutics 20100401
Preclinical evaluation of radiation and perifosine in a genetically and histologically accurate model of brainstem glioma. Cancer research 20100315
Perifosine plus nutlin-3 combination shows a synergistic anti-leukaemic activity. British journal of haematology 20100301
First-time-in-man and pharmacokinetic study of weekly oral perifosine in patients with solid tumours. European journal of cancer (Oxford, England : 1990) 20100301
Selective targeting of radiation-resistant tumor-initiating cells. Proceedings of the National Academy of Sciences of the United States of America 20100223
Induction of thyroid gene expression and radioiodine uptake in thyroid cancer cells by targeting major signaling pathways. The Journal of clinical endocrinology and metabolism 20100201
Clinical and translational studies of a phase II trial of the novel oral Akt inhibitor perifosine in relapsed or relapsed/refractory Waldenstrom's macroglobulinemia. Clinical cancer research : an official journal of the American Association for Cancer Research 20100201
Enhancing perifosine's anticancer efficacy by preventing autophagy. Autophagy 20100101
Targeting the PI3K/Akt cell survival pathway to induce cell death of HIV-1 infected macrophages with alkylphospholipid compounds. PloS one 20100101
c-Jun NH2-terminal kinase-dependent upregulation of DR5 mediates cooperative induction of apoptosis by perifosine and TRAIL. Molecular cancer 20100101
High-grade glioma mouse models and their applicability for preclinical testing. Cancer treatment reviews 20091201
Perifosine inhibits mammalian target of rapamycin signaling through facilitating degradation of major components in the mTOR axis and induces autophagy. Cancer research 20091201
The alkylphospholipid perifosine induces apoptosis and p21-mediated cell cycle arrest in medulloblastoma. Molecular cancer research : MCR 20091101
Genetic alterations in the phosphoinositide 3-kinase/Akt signaling pathway confer sensitivity of thyroid cancer cells to therapeutic targeting of Akt and mammalian target of rapamycin. Cancer research 20090915
Involvement of mitochondria and recruitment of Fas/CD95 signaling in lipid rafts in resveratrol-mediated antimyeloma and antileukemia actions. Oncogene 20090910
Long-term response in primary renal cancer to sequential antiangiogenic therapy. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20090910
Celecoxib antagonizes perifosine's anticancer activity involving a cyclooxygenase-2-dependent mechanism. Molecular cancer therapeutics 20090901
Emerging treatments for multiple myeloma: beyond immunomodulatory drugs and bortezomib. Seminars in hematology 20090401
Inhibition of breast cancer metastasis by dual liposomes to disturb complex formation. International journal of pharmaceutics 20090331
Perifosine: update on a novel Akt inhibitor. Current oncology reports 20090301
[Akt enzyme: new therapeutic target in cancer and diabetes?]. Orvosi hetilap 20090222
Ocular side effects associated with imatinib mesylate and perifosine for gastrointestinal stromal tumor. Hematology/oncology clinics of North America 20090201
Bortezomib-mediated inhibition of steroid receptor coactivator-3 degradation leads to activated Akt. Clinical cancer research : an official journal of the American Association for Cancer Research 20081115
Synergistic proapoptotic activity of recombinant TRAIL plus the Akt inhibitor Perifosine in acute myelogenous leukemia cells. Cancer research 20081115
Perifosine inhibits growth of human experimental endometrial cancers by blockade of AKT phosphorylation. European journal of obstetrics, gynecology, and reproductive biology 20081101
In vivo activity of perifosine against Leishmania amazonensis. Acta tropica 20081001
Perifosine synergistically enhances TRAIL-induced myeloma cell apoptosis via up-regulation of death receptors. Clinical cancer research : an official journal of the American Association for Cancer Research 20080815
Perifosine induces differentiation and cell death in prostate cancer cells. Cancer letters 20080808
Akt down-modulation induces apoptosis of human prostate cancer cells and synergizes with EGFR tyrosine kinase inhibitors. The Prostate 20080615
The novel Akt inhibitor, perifosine, induces caspase-dependent apoptosis and downregulates P-glycoprotein expression in multidrug-resistant human T-acute leukemia cells by a JNK-dependent mechanism. Leukemia 20080601
Targeting NF-kappaB in Waldenstrom macroglobulinemia. Blood 20080515
A Phase 2 study of perifosine in advanced or metastatic breast cancer. Breast cancer research and treatment 20080301
Ulcerative keratitis in gastrointestinal stromal tumor patients treated with perifosine. Ophthalmology 20080301
The anti-tumor alkylphospholipid perifosine is internalized by an ATP-dependent translocase activity across the plasma membrane of human KB carcinoma cells. Biochimica et biophysica acta 20080201
Targeting Akt and heat shock protein 90 produces synergistic multiple myeloma cell cytotoxicity in the bone marrow microenvironment. Clinical cancer research : an official journal of the American Association for Cancer Research 20080201
Proapoptotic activity and chemosensitizing effect of the novel Akt inhibitor perifosine in acute myelogenous leukemia cells. Leukemia 20080101
Alkylphospholipids inhibit capillary-like endothelial tube formation in vitro: antiangiogenic properties of a new class of antitumor agents. Anti-cancer drugs 20080101
Anticancer alkylphospholipids: mechanisms of action, cellular sensitivity and resistance, and clinical prospects. Current pharmaceutical design 20080101
Genome-wide identification of genetic determinants for the cytotoxicity of perifosine. Human genomics 20080101
The Akt pathway regulates survival and homing in Waldenstrom macroglobulinemia. Blood 20071215
Pharmacodynamic markers of perifosine efficacy. Clinical cancer research : an official journal of the American Association for Cancer Research 20071215
The AKT inhibitor perifosine in biochemically recurrent prostate cancer: a phase II California/Pittsburgh cancer consortium trial. Clinical genitourinary cancer 20071201
Lipid rafts and metabolic energy differentially determine uptake of anti-cancer alkylphospholipids in lymphoma versus carcinoma cells. Biochemical pharmacology 20071115
Combination treatment of prostate cancer cell lines with bioactive soy isoflavones and perifosine causes increased growth arrest and/or apoptosis. Clinical cancer research : an official journal of the American Association for Cancer Research 20071015
Targeting MEK induces myeloma-cell cytotoxicity and inhibits osteoclastogenesis. Blood 20070901
Inhibition of Akt induces significant downregulation of survivin and cytotoxicity in human multiple myeloma cells. British journal of haematology 20070901
A new class of anticancer alkylphospholipids uses lipid rafts as membrane gateways to induce apoptosis in lymphoma cells. Molecular cancer therapeutics 20070801
Alkyl phospholipid perifosine induces myeloid hyperplasia in a murine myeloma model. Experimental hematology 20070701
The alkylphospholipid perifosine induces apoptosis of human lung cancer cells requiring inhibition of Akt and activation of the extrinsic apoptotic pathway. Molecular cancer therapeutics 20070701
A novel ATP-binding cassette transporter from Leishmania is involved in transport of phosphatidylcholine analogues and resistance to alkyl-phospholipids. Molecular microbiology 20070601
In vitro activity of perifosine: a novel alkylphospholipid against the promastigote stage of Leishmania species. Parasitology research 20070401
A phase II trial of perifosine in locally advanced, unresectable, or metastatic pancreatic adenocarcinoma. American journal of clinical oncology 20070201
American Society of Hematology--48th Annual Meeting and Exposition. Updates on hematological therapies. 9-12 December 2006 Orlando, FL, USA. IDrugs : the investigational drugs journal 20070201
Edelfosine and perifosine induce selective apoptosis in multiple myeloma by recruitment of death receptors and downstream signaling molecules into lipid rafts. Blood 20070115
Perifosine may be of therapeutic usefulness in morbid obese females via inhibition of the PI3K/Akt signaling pathway. Medical hypotheses 20070101
Phase II study of daily oral perifosine in patients with advanced soft tissue sarcoma. Cancer 20061115
A phase II study of perifosine (D-21226) in patients with previously untreated metastatic or locally advanced soft tissue sarcoma: A National Cancer Institute of Canada Clinical Trials Group trial. Investigational new drugs 20060901
Phase I and pharmacokinetic study of combined treatment with perifosine and radiation in patients with advanced solid tumours. Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20060801
A phase II trial of perifosine, an oral alkylphospholipid, in recurrent or metastatic head and neck cancer. Cancer biology & therapy 20060701
Inhibition of Akt by the alkylphospholipid perifosine does not enhance the radiosensitivity of human glioma cells. Molecular cancer therapeutics 20060601
Synergistic induction of apoptosis in human leukemia T cells by the Akt inhibitor perifosine and etoposide through activation of intrinsic and Fas-mediated extrinsic cell death pathways. Molecular cancer therapeutics 20060601
Perifosine, an oral bioactive novel alkylphospholipid, inhibits Akt and induces in vitro and in vivo cytotoxicity in human multiple myeloma cells. Blood 20060515
Radiosensitization of squamous cell carcinoma by the alkylphospholipid perifosine in cell culture and xenografts. Clinical cancer research : an official journal of the American Association for Cancer Research 20060301
Enhancement of antitumor activity of the anti-EGF receptor monoclonal antibody cetuximab/C225 by perifosine in PTEN-deficient cancer cells. Oncogene 20060126
Phase II study of perifosine in previously untreated patients with metastatic melanoma. Investigational new drugs 20051201
Synthesis and biological evaluation of spin-labeled alkylphospholipid analogs. Journal of medicinal chemistry 20051006
A phase II study of perifosine in androgen independent prostate cancer. Cancer biology & therapy 20051001
Perifosine inhibits multiple signaling pathways in glial progenitors and cooperates with temozolomide to arrest cell proliferation in gliomas in vivo. Cancer research 20050815
Tumor and normal tissue pharmacokinetics of perifosine, an oral anti-cancer alkylphospholipid. Investigational new drugs 20050801
Coadministration of histone deacetylase inhibitors and perifosine synergistically induces apoptosis in human leukemia cells through Akt and ERK1/2 inactivation and the generation of ceramide and reactive oxygen species. Cancer research 20050315
A phase I trial of perifosine (NSC 639966) on a loading dose/maintenance dose schedule in patients with advanced cancer. Clinical cancer research : an official journal of the American Association for Cancer Research 20041115
In vitro combination treatment with perifosine and UCN-01 demonstrates synergism against prostate (PC-3) and lung (A549) epithelial adenocarcinoma cell lines. Clinical cancer research : an official journal of the American Association for Cancer Research 20040801
Transcriptional activation of p21(waf1/cip1) by alkylphospholipids: role of the mitogen-activated protein kinase pathway in the transactivation of the human p21(waf1/cip1) promoter by Sp1. Cancer research 20040115
Synthesis and antiproliferative activity of alkylphosphocholines. Chemistry and physics of lipids 20031201
Perifosine, a novel alkylphospholipid, inhibits protein kinase B activation. Molecular cancer therapeutics 20031101
Anti-cancer alkyl-lysophospholipids inhibit the phosphatidylinositol 3-kinase-Akt/PKB survival pathway. Anti-cancer drugs 20030201
Alkylphospholipids reversibly open epithelial tight junctions. Anticancer research 20030101
ACCESS oncology and Zentaris sign product partnership. Expert review of anticancer therapy 20021001
Phase I and pharmacological study of daily oral administration of perifosine (D-21266) in patients with advanced solid tumours. European journal of cancer (Oxford, England : 1990) 20020801
Perifosine, a novel alkylphospholipid, induces p21(WAF1) expression in squamous carcinoma cells through a p53-independent pathway, leading to loss in cyclin-dependent kinase activity and cell cycle arrest. Cancer research 20020301
Effects of miltefosine on various biochemical parameters in a panel of tumor cell lines with different sensitivities. Biochemical pharmacology 20010915
Quantitative determination of perifosine, a novel alkylphosphocholine anticancer agent, in human plasma by reversed-phase liquid chromatography-electrospray mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications 20010815
Alkyl-lysophospholipids as anticancer agents and enhancers of radiation-induced apoptosis. International journal of radiation oncology, biology, physics 20010201
Separation and quantitation of alkylphosphocholines and analogues of different liposome formulations by HPTLC. Journal of AOAC International 20010101
Genetics of glioblastoma: a window into its imaging and histopathologic variability. Radiographics : a review publication of the Radiological Society of North America, Inc
Properties