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CHR2797

CHR2797

  • CAT Number: R012769
  • CAS Number: 238750-77-1
  • Molecular Formula: C₂₁H₃₀N₂O₆
  • Molecular Weight: 406.5
  • Purity: ≥95%
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Tosedostat(cas 238750-77-1) is a proprietary orally bioavailable inhibitor of the M1 family of aminopeptidases with potential antineoplastic activity. Tosedostat is converted intracellularly into a poorly membrane-permeable active metabolite (CHR-79888) which inhibits the M1 family of aminopeptidases, particularly puromycin-sensitive aminopeptidase (PuSA), and leukotriene A4 (LTA4) hydrolase; inhibition of these aminopeptidases in tumor cells may result in amino acid deprivation, inhibition of protein synthesis due to a decrease in the intracellular free amino acid pool, an increase in the level of the proapoptotic protein Noxa, and cell death.

Catalog Number R012769
CAS Number 238750-77-1
Molecular Formula

C₂₁H₃₀N₂O₆

Purity 95%
Target Aminopeptidase
Solubility Soluble in DMSO > 10 mM
Storage Store at -20°C
InChI InChI=1S/C21H30N2O6/c1-13(2)12-16(18(24)20(26)23-28)19(25)22-17(14-8-4-3-5-9-14)21(27)29-15-10-6-7-11-15/h3-5,8-9,13,15-18,24,28H,6-7,10-12H2,1-2H3,(H,22,25)(H,23,26)/t16-,17+,18+/m1/s1
InChIKey FWFGIHPGRQZWIW-SQNIBIBYSA-N
SMILES CC(C)CC(C(C(=O)NO)O)C(=O)NC(C1=CC=CC=C1)C(=O)OC2CCCC2
Reference

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1:Phase II study of tosedostat with cytarabine or decitabine in newly diagnosed older patients with acute myeloid leukaemia or high-risk MDS. Mawad R, Becker PS, Hendrie P, Scott B, Wood BL, Dean C, Sandhu V, Deeg HJ, Walter R, Wang L, Myint H, Singer JW, Estey E, Pagel JM.Br J Haematol. 2016 Jan;172(2):238-45. doi: 10.1111/bjh.13829. Epub 2015 Nov 16. PMID: 26568032 <br />
2:X-ray crystal structures of an orally available aminopeptidase inhibitor, Tosedostat, bound to anti-malarial drug targets PfA-M1 and PfA-M17. Drinkwater N, Bamert RS, Sivaraman KK, Paiardini A, McGowan S.Proteins. 2015 Apr;83(4):789-95. doi: 10.1002/prot.24771. Epub 2015 Feb 28. PMID: 25645579 <br />
3:Tosedostat for the treatment of relapsed and refractory acute myeloid leukemia. DiNardo CD, Cortes JE.Expert Opin Investig Drugs. 2014 Feb;23(2):265-72. doi: 10.1517/13543784.2014.864276. Epub 2013 Dec 9. Review. PMID: 24313331 <br />
4:Two dosing regimens of tosedostat in elderly patients with relapsed or refractory acute myeloid leukaemia (OPAL): a randomised open-label phase 2 study. Cortes J, Feldman E, Yee K, Rizzieri D, Advani AS, Charman A, Spruyt R, Toal M, Kantarjian H.Lancet Oncol. 2013 Apr;14(4):354-62. doi: 10.1016/S1470-2045(13)70037-8. Epub 2013 Feb 28. PMID: 23453583 <br />
5:Efficacy of tosedostat, a novel, oral agent for elderly patients with relapsed or refractory acute myeloid leukemia: a review of the Phase II OPAL trial. Mathisen MS, Ravandi F.Future Oncol. 2012 Apr;8(4):351-7. doi: 10.2217/fon.12.17. Review. PMID: 22515438 <br />
6:Aminopeptidase inhibition by the novel agent CHR-2797 (tosedostat) for the therapy of acute myeloid leukemia. Jenkins C, Hewamana S, Krige D, Pepper C, Burnett A.Leuk Res. 2011 May;35(5):677-81. doi: 10.1016/j.leukres.2010.10.030. Epub 2010 Dec 9. PMID: 21145592 <br />
7:A Phase Ib dose-escalation study to evaluate safety and tolerability of the addition of the aminopeptidase inhibitor tosedostat (CHR-2797) to paclitaxel in patients with advanced solid tumours. van Herpen CM, Eskens FA, de Jonge M, Desar I, Hooftman L, Bone EA, Timmer-Bonte JN, Verweij J.Br J Cancer. 2010 Oct 26;103(9):1362-8. doi: 10.1038/sj.bjc.6605917. Epub 2010 Sep 28. PMID: 20877350 Free PMC Article<br />
8:Phase I/II clinical study of Tosedostat, an inhibitor of aminopeptidases, in patients with acute myeloid leukemia and myelodysplasia. L&#246;wenberg B, Morgan G, Ossenkoppele GJ, Burnett AK, Zachée P, Dührsen U, Dierickx D, Müller-Tidow C, Sonneveld P, Krug U, Bone E, Flores N, Richardson AF, Hooftman L, Jenkins C, Zweegman S, Davies F.J Clin Oncol. 2010 Oct 1;28(28):4333-8. doi: 10.1200/JCO.2009.27.6295. Epub 2010 Aug 23. PMID: 20733120 <br />
9:A first-in-man phase i and pharmacokinetic study on CHR-2797 (Tosedostat), an inhibitor of M1 aminopeptidases, in patients with advanced solid tumors. Reid AH, Protheroe A, Attard G, Hayward N, Vidal L, Spicer J, Shaw HM, Bone EA, Carter J, Hooftman L, Harris A, De Bono JS.Clin Cancer Res. 2009 Aug 1;15(15):4978-85. doi: 10.1158/1078-0432.CCR-09-0306. Epub 2009 Jul 28. PMID: 19638462 Free Article

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