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MedKoo Cat#: 145928 | Name: Erufosine

Description:

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

Erufosine is an experimental anticancer agent that belongs to the class of alkylphosphocholines, which are known for their ability to disrupt cellular membranes. It works by inhibiting the phosphoinositide signaling pathway, leading to changes in cell membrane dynamics and the induction of apoptosis (programmed cell death) in tumor cells. Erufosine has shown promise in preclinical studies as a potential treatment for various types of cancer, including solid tumors and hematologic malignancies. Its mechanism of action is thought to involve the modulation of cell signaling pathways, making it a candidate for targeted cancer therapy with lower toxicity compared to traditional chemotherapy.

Chemical Structure

Erufosine
Erufosine
CAS#202867-33-2

Theoretical Analysis

MedKoo Cat#: 145928

Name: Erufosine

CAS#: 202867-33-2

Chemical Formula: C28H58NO4P

Exact Mass: 503.4100

Molecular Weight: 503.75

Elemental Analysis: C, 66.76; H, 11.61; N, 2.78; O, 12.70; P, 6.15

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Erufosine; ERPC 3; ERPC-3; ERPC3;
IUPAC/Chemical Name
(Z)-docos-13-en-1-yl (3-(trimethylammonio)propyl) phosphate
InChi Key
JRNJGNRNGUZCTF-SEYXRHQNSA-N
InChi Code
1S/C28H58NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27-32-34(30,31)33-28-25-26-29(2,3)4/h12-13H,5-11,14-28H2,1-4H3/b13-12-
SMILES Code
CCCCCCCC\C=C/CCCCCCCCCCCCOP([O-])(=O)OCCC[N+](C)(C)C
Appearance
To be determined
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 503.75 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
1: Gaillard B, Seguin C, Remy JS, Pons F, Lebeau L. Erufosine (ErPC3) Cationic Prodrugs as Dual Gene Delivery Reagents for Combined Antitumor Therapy. Chemistry. 2019 Dec 5;25(68):15662-15679. doi: 10.1002/chem.201903976. Epub 2019 Nov 4. PMID: 31549752. 2: Wertheimer C, Brandlhuber U, Kook D, Mayer WJ, Laubichler P, Wolf A, Kampik A, Eibl-Lindner K. Erufosine, a phosphoinositide-3-kinase inhibitor, to mitigate posterior capsule opacification in the human capsular bag model. J Cataract Refract Surg. 2015 Jul;41(7):1484-9. doi: 10.1016/j.jcrs.2015.02.034. Epub 2015 Jul 22. PMID: 26210048. 3: Kapoor V, Zaharieva MM, Das SN, Berger MR. Erufosine simultaneously induces apoptosis and autophagy by modulating the Akt-mTOR signaling pathway in oral squamous cell carcinoma. Cancer Lett. 2012 Jun 1;319(1):39-48. doi: 10.1016/j.canlet.2011.12.032. Epub 2011 Dec 24. PMID: 22202640. 4: Dineva IK, Zaharieva MM, Konstantinov SM, Eibl H, Berger MR. Erufosine suppresses breast cancer in vitro and in vivo for its activity on PI3K, c-Raf and Akt proteins. J Cancer Res Clin Oncol. 2012 Nov;138(11):1909-17. doi: 10.1007/s00432-012-1271-6. Epub 2012 Jun 30. PMID: 22752602. 5: Bagley RG, Kurtzberg L, Rouleau C, Yao M, Teicher BA. Erufosine, an alkylphosphocholine, with differential toxicity to human cancer cells and bone marrow cells. Cancer Chemother Pharmacol. 2011 Dec;68(6):1537-46. doi: 10.1007/s00280-011-1658-0. Epub 2011 Apr 28. PMID: 21526352. 6: Ansari SS, Akgün N, Berger MR. Erufosine increases RhoB expression in oral squamous carcinoma cells independent of its tumor suppressive mode of action - a short report. Cell Oncol (Dordr). 2017 Feb;40(1):89-96. doi: 10.1007/s13402-016-0302-8. Epub 2016 Nov 3. PMID: 27812856. 7: Tzoneva R, Stoyanova T, Petrich A, Popova D, Uzunova V, Momchilova A, Chiantia S. Effect of Erufosine on Membrane Lipid Order in Breast Cancer Cell Models. Biomolecules. 2020 May 22;10(5):802. doi: 10.3390/biom10050802. PMID: 32455962; PMCID: PMC7277205. 8: Abdik H. Antineoplastic effects of erufosine on small cell and non-small cell lung cancer cells through induction of apoptosis and cell cycle arrest. Mol Biol Rep. 2022 Apr;49(4):2963-2971. doi: 10.1007/s11033-022-07117-6. Epub 2022 Jan 11. PMID: 35015224. 9: Königs SK, Pallasch CP, Lindner LH, Schwamb J, Schulz A, Brinker R, Claasen J, Veldurthy A, Eibl H, Hallek M, Wendtner CM. Erufosine, a novel alkylphosphocholine, induces apoptosis in CLL through a caspase-dependent pathway. Leuk Res. 2010 Aug;34(8):1064-9. doi: 10.1016/j.leukres.2009.12.003. Epub 2010 Jan 21. PMID: 20092894. 10: Zaharieva MM, Konstantinov SM, Pilicheva B, Karaivanova M, Berger MR. Erufosine: a membrane targeting antineoplastic agent with signal transduction modulating effects. Ann N Y Acad Sci. 2007 Jan;1095:182-92. doi: 10.1196/annals.1397.022. PMID: 17404031. 11: Yosifov DY, Todorov PT, Zaharieva MM, Georgiev KD, Pilicheva BA, Konstantinov SM, Berger MR. Erucylphospho-N,N,N-trimethylpropylammonium (erufosine) is a potential antimyeloma drug devoid of myelotoxicity. Cancer Chemother Pharmacol. 2011 Jan;67(1):13-25. doi: 10.1007/s00280-010-1273-5. Epub 2010 Feb 23. PMID: 20177898. 12: Avsar Abdik E, Kaleagasioglu F, Abdik H, Sahin F, Berger MR. ABT-737 and erufosine combination against castration-resistant prostate cancer: a promising but cell-type specific response associated with the modulation of anti-apoptotic signaling. Anticancer Drugs. 2019 Apr;30(4):383-393. doi: 10.1097/CAD.0000000000000736. PMID: 30557204. 13: Trochopoulos AGX, Ilieva Y, Kroumov AD, Dimitrova LL, Pencheva-El Tibi I, Philipov S, Berger MR, Najdenski HM, Yoncheva K, Konstantinov SM, Zaharieva MM. Micellar Curcumin Substantially Increases the Antineoplastic Activity of the Alkylphosphocholine Erufosine against TWIST1 Positive Cutaneous T Cell Lymphoma Cell Lines. Pharmaceutics. 2022 Dec 1;14(12):2688. doi: 10.3390/pharmaceutics14122688. PMID: 36559182; PMCID: PMC9781439. 14: Kaleağasıoğlu F, Berger MR. Differential effects of erufosine on proliferation, wound healing and apoptosis in colorectal cancer cell lines. Oncol Rep. 2014 Mar;31(3):1407-16. doi: 10.3892/or.2013.2942. Epub 2013 Dec 20. PMID: 24366062. 15: Fiegl M, Lindner LH, Juergens M, Eibl H, Hiddemann W, Braess J. Erufosine, a novel alkylphosphocholine, in acute myeloid leukemia: single activity and combination with other antileukemic drugs. Cancer Chemother Pharmacol. 2008 Jul;62(2):321-9. doi: 10.1007/s00280-007-0612-7. Epub 2007 Oct 6. PMID: 17922125; PMCID: PMC2755757. 16: Ansari SS, Sharma AK, Soni H, Ali DM, Tews B, König R, Eibl H, Berger MR. Induction of ER and mitochondrial stress by the alkylphosphocholine erufosine in oral squamous cell carcinoma cells. Cell Death Dis. 2018 Feb 20;9(3):296. doi: 10.1038/s41419-018-0342-2. PMID: 29463797; PMCID: PMC5833417. 17: Henke G, Lindner LH, Vogeser M, Eibl HJ, Wörner J, Müller AC, Bamberg M, Wachholz K, Belka C, Jendrossek V. Pharmacokinetics and biodistribution of Erufosine in nude mice--implications for combination with radiotherapy. Radiat Oncol. 2009 Oct 23;4:46. doi: 10.1186/1748-717X-4-46. PMID: 19852786; PMCID: PMC2773776. 18: Chometon G, Cappuccini F, Raducanu A, Aumailley M, Jendrossek V. The membrane-targeted alkylphosphocholine erufosine interferes with survival signals from the extracellular matrix. Anticancer Agents Med Chem. 2014 May;14(4):578-91. doi: 10.2174/1871520614666140313120417. PMID: 24628265. 19: Henke G, Meier V, Lindner LH, Eibl H, Bamberg M, Belka C, Budach W, Jendrossek V. Effects of ionizing radiation in combination with Erufosine on T98G glioblastoma xenograft tumours: a study in NMRI nu/nu mice. Radiat Oncol. 2012 Oct 18;7:172. doi: 10.1186/1748-717X-7-172. PMID: 23078969; PMCID: PMC3539870. 20: Ansari SS, Sharma AK, Zepp M, Ivanova E, Bergmann F, König R, Berger MR. Upregulation of cell cycle genes in head and neck cancer patients may be antagonized by erufosine's down regulation of cell cycle processes in OSCC cells. Oncotarget. 2017 Dec 20;9(5):5797-5810. doi: 10.18632/oncotarget.23537. PMID: 29464035; PMCID: PMC5814175.