Perifosine (BioDeep_00000182272)
human metabolite blood metabolite
代谢物信息卡片
1,1-dimethyl-4-{[(octadecyloxy)phosphinato]oxy}piperidin-1-ium
化学式: C25H52NO4P (461.36337620000006)
中文名称: 哌立福新
谱图信息:
最多检出来源 Mus musculus(blood) 87.5%
分子结构信息
SMILES: CCCCCCCCCCCCCCCCCCOP(=O)([O-])OC1CC[N+](CC1)(C)C
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
描述信息
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C2188 - Alkylphosphocholine Compound
C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C61074 - Serine/Threonine Kinase Inhibitor
C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer
Perifosine is an oral Akt inhibitor which inhibits proliferation of different tumor cell lines with IC50s of 0.6-8.9 μM.
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:67272
- PubChem: 148177
- HMDB: HMDB0256342
- DrugBank: DB06641
- ChEMBL: CHEMBL372764
- Wikipedia: Perifosine
- chemspider: 130628
- CAS: 157716-52-4
- medchemexpress: HY-50909
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Xueyao Yin, Zhiye Xu, Xinxin Zhang, Jiahua Wu, Weina Lu. 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 (Georgetown, Tex.).
2023 Jan; ?(?):1-19. doi:
10.1080/15384101.2023.2169521. [PMID: 36710409] - P F She, L L Xu, Y Q Liu, Z H Li, S S Liu, Y M Li, L Y Zhou, Y Wu. [Perifosine inhibits biofilm formation of Pseudomonas aeruginosa by interacting with PqsE protein].
Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine].
2022 Feb; 56(2):192-196. doi:
10.3760/cma.j.cn112150-20211020-00970. [PMID: 35184449] - Carolina Hassibe Thomé, Germano Aguiar Ferreira, Diego Antonio Pereira-Martins, Guilherme Augusto Dos Santos, César Alexander Ortiz, Lucas Eduardo Botelho de Souza, Lays Martins Sobral, Cleide Lúcia Araújo Silva, Priscila Santos Scheucher, Cristiane Damas Gil, Andréia Machado Leopoldino, Douglas R A Silveira, Juan L Coelho-Silva, Fabíola Traina, Luisa C Koury, Raul A M Melo, Rosane Bittencourt, Katia Pagnano, Ricardo Pasquini, Elenaide C Nunes, Evandro M Fagundes, Ana Beatriz F Gloria, Fábio Rodrigues Kerbauy, Maria de Lourdes Chauffaille, Armand Keating, Martin S Tallman, Raul C Ribeiro, Richard Dillon, Arnold Ganser, Bob Löwenberg, Peter Valk, Francesco Lo-Coco, Miguel A Sanz, Nancy Berliner, Vitor Marcel Faça, Eduardo M Rego. NTAL is associated with treatment outcome, cell proliferation and differentiation in acute promyelocytic leukemia.
Scientific reports.
2020 06; 10(1):10315. doi:
10.1038/s41598-020-66223-2. [PMID: 32587277] - Germano Aguiar Ferreira, Carolina Hassibe Thomé, Ana Maria Sper Simão, Priscila Santos Scheucher, Cleide Lúcia Araújo Silva, Fernando Chahud, Pietro Ciancaglini, Andreia Machado Leopoldino, Eduardo Magalhães Rego, Vitor Marcel Faça, Guilherme Augusto Dos Santos. The lipid raft protein NTAL participates in AKT signaling in mantle cell lymphoma.
Leukemia & lymphoma.
2019 11; 60(11):2658-2668. doi:
10.1080/10428194.2019.1607326. [PMID: 31060403] - Jeremy S Logue, Alexander X Cartagena-Rivera, Richard S Chadwick. c-Src activity is differentially required by cancer cell motility modes.
Oncogene.
2018 04; 37(16):2104-2121. doi:
10.1038/s41388-017-0071-5. [PMID: 29379163] - Masayuki Yamaji, Akinobu Ota, Md Wahiduzzaman, Sivasundaram Karnan, Toshinori Hyodo, Hiroyuki Konishi, Shinobu Tsuzuki, Yoshitaka Hosokawa, Masayuki Haniuda. Novel ATP-competitive Akt inhibitor afuresertib suppresses the proliferation of malignant pleural mesothelioma cells.
Cancer medicine.
2017 Nov; 6(11):2646-2659. doi:
10.1002/cam4.1179. [PMID: 28960945] - Kimikazu Matsumoto, Hiroyuki Shichino, Hiroshi Kawamoto, Yoshiyuki Kosaka, Motoaki Chin, Koji Kato, Hideo Mugishima. Phase I study of perifosine monotherapy in patients with recurrent or refractory neuroblastoma.
Pediatric blood & cancer.
2017 Nov; 64(11):. doi:
10.1002/pbc.26623. [PMID: 28521076] - James C League-Pascual, Cynthia M Lester-McCully, Shaefali Shandilya, Lukas Ronner, Louis Rodgers, Rafael Cruz, Cody J Peer, William D Figg, Katherine E Warren. Plasma and cerebrospinal fluid pharmacokinetics of select chemotherapeutic agents following intranasal delivery in a non-human primate model.
Journal of neuro-oncology.
2017 05; 132(3):401-407. doi:
10.1007/s11060-017-2388-x. [PMID: 28290002] - Brian H Kushner, Nai-Kong V Cheung, Shakeel Modak, Oren J Becher, Ellen M Basu, Stephen S Roberts, Kim Kramer, Ira J Dunkel. A phase I/Ib trial targeting the Pi3k/Akt pathway using perifosine: Long-term progression-free survival of patients with resistant neuroblastoma.
International journal of cancer.
2017 Jan; 140(2):480-484. doi:
10.1002/ijc.30440. [PMID: 27649927] - Pablo Ríos-Marco, Antonio Ríos, José M Jiménez-López, María P Carrasco, Carmen Marco. Cholesterol homeostasis and autophagic flux in perifosine-treated human hepatoblastoma HepG2 and glioblastoma U-87 MG cell lines.
Biochemical pharmacology.
2015 Jul; 96(1):10-9. doi:
10.1016/j.bcp.2015.04.015. [PMID: 25934232] - Diane E Cole, Cynthia M Lester-McCully, Brigitte C Widemann, Katherine E Warren. Plasma and cerebrospinal fluid pharmacokinetics of the Akt inhibitor, perifosine, in a non-human primate model.
Cancer chemotherapy and pharmacology.
2015 May; 75(5):923-8. doi:
10.1007/s00280-015-2711-1. [PMID: 25740692] - Anze Testen, Rok Podlipec, Janez Mravljak, Andrea Orthmann, Marjeta Šentjurc, Reiner Zeisig, Janez Štrancar, Tilen Koklic. How perifosine affects liposome-encapsulated drug delivery across a cell barrier.
Therapeutic delivery.
2015; 6(4):423-41. doi:
10.4155/tde.14.127. [PMID: 25996042] - William D Figg, Manish Monga, Donna Headlee, Avni Shah, Cindy H Chau, Cody Peer, Richard Messman, Yusri A Elsayed, Anthony J Murgo, Giovanni Melillo, Qin C Ryan, Mikhail Kalnitskiy, Adrian M Senderowicz, Melinda Hollingshead, Susan G Arbuck, Edward A Sausville. A phase I and pharmacokinetic study of oral perifosine with different loading schedules in patients with refractory neoplasms.
Cancer chemotherapy and pharmacology.
2014 Nov; 74(5):955-67. doi:
10.1007/s00280-014-2569-7. [PMID: 25183650] - Tilen Koklic. Perifosine induced release of contents of trans cell-barrier transport efficient liposomes.
Chemistry and physics of lipids.
2014 Oct; 183(?):50-9. doi:
10.1016/j.chemphyslip.2014.05.006. [PMID: 24863642] - Joachim Fensterle, Babette Aicher, Irene Seipelt, Michael Teifel, Juergen Engel. Current view on the mechanism of action of perifosine in cancer.
Anti-cancer agents in medicinal chemistry.
2014 May; 14(4):629-35. doi:
10.2174/1871520614666140309225912. [PMID: 24628236] - Wim J van Blitterswijk, Marcel Verheij. Anticancer mechanisms and clinical application of alkylphospholipids.
Biochimica et biophysica acta.
2013 Mar; 1831(3):663-74. doi:
10.1016/j.bbalip.2012.10.008. [PMID: 23137567] - Neeharika Srivastava, Daniel C Cho. Perifosine in renal cell carcinoma.
Expert opinion on investigational drugs.
2013 Feb; 22(2):285-91. doi:
10.1517/13543784.2013.754422. [PMID: 23253151] - Daniel C Cho, Thomas E Hutson, Wolfram Samlowski, Peter Sportelli, Brad Somer, Paul Richards, Jeffrey A Sosman, Igor Puzanov, M Dror Michaelson, Keith T Flaherty, Robert A Figlin, Nicholas J Vogelzang. Two phase 2 trials of the novel Akt inhibitor perifosine in patients with advanced renal cell carcinoma after progression on vascular endothelial growth factor-targeted therapy.
Cancer.
2012 Dec; 118(24):6055-62. doi:
10.1002/cncr.27668. [PMID: 22674198] - Rok Podlipec, Tilen Koklic, Janez Strancar, Janez Mravljak, Marjeta Sentjurc. Influence of cancerostatic perifosine on membrane fluidity of liposomes and different cell lines as measured by electron paramagnetic resonance.
Croatian medical journal.
2012 Dec; 53(6):558-67. doi:
10.3325/cmj.2012.53.558. [PMID: 23275321] - Carolina H Thomé, Guilherme A dos Santos, Germano A Ferreira, Priscila S Scheucher, Clarice Izumi, Andreia M Leopoldino, Ana Maria Simão, Pietro Ciancaglini, Kleber T de Oliveira, Alice Chin, Samir M Hanash, Roberto P Falcão, Eduardo M Rego, Lewis J Greene, Vitor M Faça. 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.
2012 Dec; 11(12):1898-912. doi:
10.1074/mcp.m112.019661. [PMID: 23001822] - Martin Schmidt-Hieber, Robert Dabrowski, Babette Aicher, Philipp Lohneis, Antonia Busse, Carola Tietze-Buerger, Birgit Reufi, Eckhard Thiel, Igor Wolfgang Blau. In vitro effects of perifosine, bortezomib and lenalidomide against hematopoietic progenitor cells from healthy donors.
Investigational new drugs.
2012 Aug; 30(4):1396-403. doi:
10.1007/s10637-011-9705-6. [PMID: 21750922] - J J Gills, C Zhang, M S Abu-Asab, S S Castillo, C Marceau, J LoPiccolo, A P Kozikowski, M Tsokos, T Goldkorn, P A Dennis. Ceramide mediates nanovesicle shedding and cell death in response to phosphatidylinositol ether lipid analogs and perifosine.
Cell death & disease.
2012 Jul; 3(?):e340. doi:
10.1038/cddis.2012.72. [PMID: 22764099] - Maria Theresa E Montales, Omar M Rahal, Jie Kang, Theodore J Rogers, Ronald L Prior, Xianli Wu, Rosalia C M Simmen. 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.
2012 Mar; 33(3):652-60. doi:
10.1093/carcin/bgr317. [PMID: 22219179] - William S Holland, Clifford G Tepper, Jose E Pietri, Danielle C Chinn, David R Gandara, Philip C Mack, Primo N Lara. Evaluating rational non-cross-resistant combination therapy in advanced clear cell renal cell carcinoma: combined mTOR and AKT inhibitor therapy.
Cancer chemotherapy and pharmacology.
2012 Jan; 69(1):185-94. doi:
10.1007/s00280-011-1684-y. [PMID: 21644050] - Francisco Muñoz-Martínez, Cristina Torres, Santiago Castanys, Francisco Gamarro. CDC50A plays a key role in the uptake of the anticancer drug perifosine in human carcinoma cells.
Biochemical pharmacology.
2010 Sep; 80(6):793-800. doi:
10.1016/j.bcp.2010.05.017. [PMID: 20510206] - José Batista, Tim Friedrichson, Georg Schlechtingen, Tobias Braxmeier, Gary Jennings, Jürgen Bajorath. Computational screening for membrane-directed inhibitors of mast cell activation.
European journal of medicinal chemistry.
2010 Jun; 45(6):2700-4. doi:
10.1016/j.ejmech.2010.01.061. [PMID: 20153565] - María P Carrasco, José M Jiménez-López, Pablo Ríos-Marco, Josefa L Segovia, Carmen Marco. Disruption of cellular cholesterol transport and homeostasis as a novel mechanism of action of membrane-targeted alkylphospholipid analogues.
British journal of pharmacology.
2010 May; 160(2):355-66. doi:
10.1111/j.1476-5381.2010.00689.x. [PMID: 20423345] - Nicholas J Vogelzang, Wolfram Samlowski, Alan Weissman. Long-term response in primary renal cancer to sequential antiangiogenic therapy.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2009 Sep; 27(26):e106-7. doi:
10.1200/jco.2009.23.4021. [PMID: 19667262] - M Reis-Sobreiro, C Gajate, F Mollinedo. Involvement of mitochondria and recruitment of Fas/CD95 signaling in lipid rafts in resveratrol-mediated antimyeloma and antileukemia actions.
Oncogene.
2009 Sep; 28(36):3221-34. doi:
10.1038/onc.2009.183. [PMID: 19561642] - Jane Wenzel, Reiner Zeisig, Iduna Fichtner. Inhibition of breast cancer metastasis by dual liposomes to disturb complex formation.
International journal of pharmaceutics.
2009 Mar; 370(1-2):121-8. doi:
10.1016/j.ijpharm.2008.11.023. [PMID: 19100823] - Joell J Gills, Phillip A Dennis. Perifosine: update on a novel Akt inhibitor.
Current oncology reports.
2009 Mar; 11(2):102-10. doi:
10.1007/s11912-009-0016-4. [PMID: 19216841] - Gustavo Ayala, Jun Yan, Rile Li, Yi Ding, Timothy C Thompson, Martha P Mims, Teresa G Hayes, Vivian MacDonnell, R Garret Lynch, Anna Frolov, Brian J Miles, Thomas M Wheeler, J Wade Harper, Ming-Jer Tsai, Michael M Ittmann, Dov Kadmon. 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.
2008 Nov; 14(22):7511-8. doi:
10.1158/1078-0432.ccr-08-0839. [PMID: 19010869] - Esther Castanys-Muñoz, José María Pérez-Victoria, Francisco Gamarro, Santiago Castanys. Characterization of an ABCG-like transporter from the protozoan parasite Leishmania with a role in drug resistance and transbilayer lipid movement.
Antimicrobial agents and chemotherapy.
2008 Oct; 52(10):3573-9. doi:
10.1128/aac.00587-08. [PMID: 18644961] - Daniel Floryk, Timothy C Thompson. Perifosine induces differentiation and cell death in prostate cancer cells.
Cancer letters.
2008 Aug; 266(2):216-26. doi:
10.1016/j.canlet.2008.02.060. [PMID: 18395973] - F Chiarini, M Del Sole, S Mongiorgi, G C Gaboardi, A Cappellini, I Mantovani, M Y Follo, J A McCubrey, A M Martelli. 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.
2008 Jun; 22(6):1106-16. doi:
10.1038/leu.2008.79. [PMID: 18385752] - Francisco Muñoz-Martínez, Cristina Torres, Santiago Castanys, Francisco Gamarro. 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.
2008 Feb; 1778(2):530-40. doi:
10.1016/j.bbamem.2007.10.017. [PMID: 18005660] - V Papa, P L Tazzari, F Chiarini, A Cappellini, F Ricci, A M Billi, C Evangelisti, E Ottaviani, G Martinelli, N Testoni, J A McCubrey, A M Martelli. Proapoptotic activity and chemosensitizing effect of the novel Akt inhibitor perifosine in acute myelogenous leukemia cells.
Leukemia.
2008 Jan; 22(1):147-60. doi:
10.1038/sj.leu.2404980. [PMID: 17928881] - Wim J van Blitterswijk, Marcel Verheij. Anticancer alkylphospholipids: mechanisms of action, cellular sensitivity and resistance, and clinical prospects.
Current pharmaceutical design.
2008; 14(21):2061-74. doi:
10.2174/138161208785294636. [PMID: 18691116] - Stefan R Vink, Arnold H van der Luit, Jeffrey B Klarenbeek, Marcel Verheij, Wim J van Blitterswijk. Lipid rafts and metabolic energy differentially determine uptake of anti-cancer alkylphospholipids in lymphoma versus carcinoma cells.
Biochemical pharmacology.
2007 Nov; 74(10):1456-65. doi:
10.1016/j.bcp.2007.07.041. [PMID: 17803969] - Arnold H van der Luit, Stefan R Vink, Jeffrey B Klarenbeek, Daniel Perrissoud, Eric Solary, Marcel Verheij, Wim J van Blitterswijk. A new class of anticancer alkylphospholipids uses lipid rafts as membrane gateways to induce apoptosis in lymphoma cells.
Molecular cancer therapeutics.
2007 Aug; 6(8):2337-45. doi:
10.1158/1535-7163.mct-07-0202. [PMID: 17699729] - Esther Castanys-Muñoz, Nele Alder-Baerens, Thomas Pomorski, Francisco Gamarro, Santiago Castanys. A novel ATP-binding cassette transporter from Leishmania is involved in transport of phosphatidylcholine analogues and resistance to alkyl-phospholipids.
Molecular microbiology.
2007 Jun; 64(5):1141-53. doi:
10.1111/j.1365-2958.2007.05653.x. [PMID: 17542911] - Consuelo Gajate, Faustino Mollinedo. Edelfosine and perifosine induce selective apoptosis in multiple myeloma by recruitment of death receptors and downstream signaling molecules into lipid rafts.
Blood.
2007 Jan; 109(2):711-9. doi:
10.1182/blood-2006-04-016824. [PMID: 17003375] - Howard H Bailey, Michelle R Mahoney, David S Ettinger, William J Maples, Paula M Fracasso, Anne M Traynor, Charles Erlichman, Scott H Okuno. Phase II study of daily oral perifosine in patients with advanced soft tissue sarcoma.
Cancer.
2006 Nov; 107(10):2462-7. doi:
10.1002/cncr.22308. [PMID: 17058289] - Stefan R Vink, Jan H M Schellens, Jos H Beijnen, Herbert Sindermann, Jürgen Engel, Ria Dubbelman, Gemi Moppi, Michel J X Hillebrand, Harry Bartelink, Marcel Verheij. 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.
2006 Aug; 80(2):207-13. doi:
10.1016/j.radonc.2006.07.032. [PMID: 16914220] - Stefan R Vink, Saskia Lagerwerf, Elly Mesman, Jan H M Schellens, Adrian C Begg, Wim J van Blitterswijk, Marcel Verheij. 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.
2006 Mar; 12(5):1615-22. doi:
10.1158/1078-0432.ccr-05-2033. [PMID: 16533789] - Stefan R Vink, Jan H M Schellens, Wim J van Blitterswijk, Marcel Verheij. Tumor and normal tissue pharmacokinetics of perifosine, an oral anti-cancer alkylphospholipid.
Investigational new drugs.
2005 Aug; 23(4):279-86. doi:
10.1007/s10637-005-1436-0. [PMID: 16012787] - Lynn Van Ummersen, Kim Binger, Jennifer Volkman, Rebecca Marnocha, Kendra Tutsch, Jill Kolesar, Rhoda Arzoomanian, Dona Alberti, George Wilding. 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.
2004 Nov; 10(22):7450-6. doi:
10.1158/1078-0432.ccr-03-0406. [PMID: 15569974] - Sudhir B Kondapaka, Sheo S Singh, Girija P Dasmahapatra, Edward A Sausville, Krishnendu K Roy. Perifosine, a novel alkylphospholipid, inhibits protein kinase B activation.
Molecular cancer therapeutics.
2003 Nov; 2(11):1093-103. doi:
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Anticancer research.
2003 Jan; 23(1A):27-32. doi:
NULL. [PMID: 12680191] - E W Woo, R Messmann, E A Sausville, W D Figg. 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.
2001 Aug; 759(2):247-57. doi:
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International journal of radiation oncology, biology, physics.
2001 Feb; 49(2):415-9. doi:
10.1016/s0360-3016(00)01476-0. [PMID: 11173135] - N G Knebel, S Grieb, M Winkler, M Locher, E van der Vlis, E R Verheij. Quantification of perifosine, an alkylphosphocholine anti-tumour agent, in plasma by pneumatically assisted electrospray tandem mass spectrometry coupled with high-performance liquid chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
1999 Jan; 721(2):257-69. doi:
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