WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H202890
CAS#: 92981-78-7 (HCl)
Description: Tesmilifene, also known as YMB1002 and Depmpe, is a novel, small molecule that selectively targets multiple-drug resistant (MDR) tumor cells, sensitizing them to chemotherapy. Tesmilifene may offer clinical benefit in a number of tumor types and is being tested with a variety of chemotherapeutic regimens
Hodoodo Cat#: H202890
Name: Tesmilifene HCl
CAS#: 92981-78-7 (HCl)
Chemical Formula: C19H26ClNO
Exact Mass: 283.19
Molecular Weight: 319.870
Elemental Analysis: C, 71.34; H, 8.19; Cl, 11.08; N, 4.38; O, 5.00
Related CAS #: 92981-78-7 (HCl) 98774-23-3 (free base)
Synonym: Tesmilifene; YMB1002; YMB 1002; YMB-1002; Depmpe.
IUPAC/Chemical Name: 2-(4-benzylphenoxy)-N,N-diethylethanamine hydrochloride
InChi Key: TXLHNFOLHRXMAU-UHFFFAOYSA-N
InChi Code: InChI=1S/C19H25NO.ClH/c1-3-20(4-2)14-15-21-19-12-10-18(11-13-19)16-17-8-6-5-7-9-17;/h5-13H,3-4,14-16H2,1-2H3;1H
SMILES Code: CCN(CC)CCOC1=CC=C(CC2=CC=CC=C2)C=C1.[H]Cl
Appearance: Solid powder
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: Soluble in DMSO, not in water
Shelf Life: >5 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: Related CAS# 92981-78-7 (Tesmilifene hydrochloride) 98774-23-3 ( (Tesmilifene free base))
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The following data is based on the product molecular weight 319.87 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Deng T, Liu JC, Pritchard KI, Eisen A, Zacksenhaus E. Preferential killing of breast tumor initiating cells by N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine/tesmilifene. Clin Cancer Res. 2009 Jan 1;15(1):119-30. PubMed PMID: 19118039.
2: Ferguson PJ, Brisson AR, Koropatnick J, Vincent MD. Enhancement of cytotoxicity of natural product drugs against multidrug resistant variant cell lines of human head and neck squamous cell carcinoma and breast carcinoma by tesmilifene. Cancer Lett. 2009 Feb 18;274(2):279-89. Epub 2008 Nov 4. PubMed PMID: 18986763.
3: Xu FY, Queen G, Brandes L, Hatch GM. The phospholipidosis-lnducing potential of the chemopotentiating drug, N,N-Diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine (DPPE, tesmilifene) correlates with its stimulation of phosphatidylserine synthesis and exposure on the plasma membrane in MCF-7 breast cancer cells. Proc West Pharmacol Soc. 2007;50:61-3. PubMed PMID: 18605231.
4: Brandes LJ. N,N-diethyl-2-[4-(phenylmethyl) phenoxy] ethanamine (DPPE; tesmilifene), a chemopotentiating agent with hormetic effects on DNA synthesis in vitro, may improve survival in patients with metastatic breast cancer. Hum Exp Toxicol. 2008 Feb;27(2):143-7. PubMed PMID: 18480139.
5: Kase K, Goswami A, Ohtaki K, Tanabe E, Saino N, Okamoto S. On-demand generation of an efficient catalyst for pyridine formation from unactivated nitriles and alpha,omega-diynes using CoCl2-6H2O, dppe, and Zn. Org Lett. 2007 Mar 1;9(5):931-4. Epub 2007 Jan 30. PubMed PMID: 17261007.
6: Liu J, Tu D, Dancey J, Reyno L, Pritchard KI, Pater J, Seymour LK. Quality of life analyses in a clinical trial of DPPE (tesmilifene) plus doxorubicin versus doxorubicin in patients with advanced or metastatic breast cancer: NCIC CTG Trial MA.19. Breast Cancer Res Treat. 2006 Dec;100(3):263-71. Epub 2006 Jul 6. PubMed PMID: 16823511.
7: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 May;28(4):233-77. PubMed PMID: 16801985.
8: Vincent M. Tesmilifene may enhance breast cancer chemotherapy by killing a clone of aggressive, multi-drug resistant cells through its action on the p-glycoprotein pump. Med Hypotheses. 2006;66(4):715-31. Epub 2006 Jan 18. PubMed PMID: 16413681.
9: Raghavan D, Brandes LJ, Klapp K, Snyder T, Styles E, Tsao-Wei D, Lieskovsky G, Quinn DI, Ramsey EW. Phase II trial of tesmilifene plus mitoxantrone and prednisone for hormone refractory prostate cancer: high subjective and objective response in patients with symptomatic metastases. J Urol. 2005 Nov;174(5):1808-13; discussion 1813. PubMed PMID: 16217292.
10: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Apr;26(3):211-44. PubMed PMID: 15148527.
11: Reyno L, Seymour L, Tu D, Dent S, Gelmon K, Walley B, Pluzanska A, Gorbunova V, Garin A, Jassem J, Pienkowski T, Dancey J, Pearce L, MacNeil M, Marlin S, Lebwohl D, Voi M, Pritchard K; National Cancer Institute of Canada Clinical Trials Group Study MA.19. Phase III study of N,N-diethyl-2-[4-(phenylmethyl) phenoxy]ethanamine (BMS-217380-01) combined with doxorubicin versus doxorubicin alone in metastatic/recurrent breast cancer: National Cancer Institute of Canada Clinical Trials Group Study MA.19. J Clin Oncol. 2004 Jan 15;22(2):269-76. PubMed PMID: 14722035.
12: Deli MA, Abrahám CS, Niwa M, Falus A. N,N-diethyl-2-[4-(phenylmethyl)phenoxy]ethanamine increases the permeability of primary mouse cerebral endothelial cell monolayers. Inflamm Res. 2003 Apr;52 Suppl 1:S39-40. PubMed PMID: 12755402.
13: Bencsáth M, Gidáli J, Brandes LJ, Falus A. Murine and human hematopoietic colony formation: a possible regulatory role for intracellular histamine. Acta Biol Hung. 2002;53(3):299-306. PubMed PMID: 12371609.
14: Szincsák N, Hegyesi H, Hunyadi J, Martin G, Lázár-Molnár E, Kovács P, Rivera E, Falus A, Juhász I. Cimetidine and a tamoxifen derivate reduce tumour formation in SCID mice xenotransplanted with a human melanoma cell line. Melanoma Res. 2002 Jun;12(3):231-40. PubMed PMID: 12140379.
15: Veszely G, Fürész J, Pállinger E, Horkay B, Falus A. Effect of alpha-FMH and DPPE on colony-forming properties of human peripheral progenitor cells. Curr Med Chem. 2002 Jul;9(14):1349-57. PubMed PMID: 12132991.
16: Mésange F, Sebbar M, Capdevielle J, Guillemot JC, Ferrara P, Bayard F, Poirot M, Faye JC. Identification of two tamoxifen target proteins by photolabeling with 4-(2-morpholinoethoxy)benzophenone. Bioconjug Chem. 2002 Jul-Aug;13(4):766-72. PubMed PMID: 12121132.
17: László V, Rothe G, Hegyesi H, Szeberényi JB, Orsó E, Schmitz G, Falus A. Increased histidine decarboxylase expression during in vitro monocyte maturation; a possible role of endogenously synthesised histamine in monocyte/macrophage differentiation. Inflamm Res. 2001 Aug;50(8):428-34. PubMed PMID: 11556524.
18: Brandes LJ, Queen GM, LaBella FS. N,N-diethyl-2-[4-(phenylmethyl)phenoxy] ethanamine (DPPE) a chemopotentiating and cytoprotective agent in clinical trials: interaction with histamine at cytochrome P450 3A4 and other isozymes that metabolize antineoplastic drugs. Cancer Chemother Pharmacol. 2000;45(4):298-304. PubMed PMID: 10755318.
19: Poirot M, De Medina P, Delarue F, Perie JJ, Klaebe A, Faye JC. Synthesis, binding and structure-affinity studies of new ligands for the microsomal anti-estrogen binding site (AEBS). Bioorg Med Chem. 2000 Aug;8(8):2007-16. PubMed PMID: 11003145.
20: Lebwohl DE, Canetta R. New developments in chemotherapy of advanced breast cancer. Ann Oncol. 1999;10 Suppl 6:139-46. Review. PubMed PMID: 10676565.
