WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205648
Description: Tosedostat 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.
MedKoo Cat#: 205648
Chemical Formula: C21H30N2O6
Exact Mass: 406.21039
Molecular Weight: 406.47
Elemental Analysis: C, 62.05; H, 7.44; N, 6.89; O, 23.62
Synonym: CHR2797; CHR-2797; CHR 2797; Tosedostat.
IUPAC/Chemical Name: (S)-cyclopentyl 2-((R)-2-((S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4-methylpentanamido)-2-phenylacetate
InChi Key: FWFGIHPGRQZWIW-SQNIBIBYSA-N
InChi Code: 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
SMILES Code: O=C(OC1CCCC1)[C@@H](NC([C@@H]([C@H](O)C(NO)=O)CC(C)C)=O)C2=CC=CC=C2
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
The following data is based on the product molecular weight 406.47 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|
1. Aminopeptidase inhibition by the novel agent CHR-2797 (tosedostat) for the therapy of acute myeloid leukemia By Jenkins, Christopher; Hewamana, Saman; Krige, David; Pepper, Chris; Burnett, Alan From Leukemia Research (2011), 35(5), 677-681.
2. Phase I/II clinical study of tosedostat, an inhibitor of aminopeptidases, in patients with acute myeloid leukemia and myelodysplasia By Loewenberg, Bob; Morgan, Gareth; Ossenkoppele, Gert I.; Burnett, Alan K.; Zachee, Pierre; Duehrsen, Ulrich; Dierickx, Daan; Mueller-Tidow, Carsten; Sonneveld, Pieter; Krug, Utz; et al From Journal of Clinical Oncology (2010), 28(28), 4333-4338.
3. 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 By van Herpen, C. M. L.; Eskens, F. A. L. M.; de Jonge, M.; Desar, I.; Hooftman, L.; Bone, E. A.; Timmer-Bonte, J. N. H.; Verweij, J. From British Journal of Cancer (2010), 103(9), 1362-1368.
4. Quinazoline derivatives and methods of treatment By Tung, Roger From U.S. Pat. Appl. Publ. (2010), US 20100260674 A1 20101014.
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6. Starving to succeed By Davenport, Emma L.; Aronson, Lauren I.; Davies, Faith E. From Autophagy (2009), 5(7), 1052-1054.
7. Gene expression biomarkers of aminopeptidase inhibition in tumor-derived cell lines By Krige, David; Drummond, Alan Hastings From PCT Int. Appl. (2009), WO 2009098451 A2 20090813.
8. A First-in-Man Phase I and Pharmacokinetic Study on CHR-2797 (Tosedostat), an Inhibitor of M1 Aminopeptidases, in Patients with Advanced Solid Tumors By Reid, Alison H. M.; Protheroe, Andrew; Attard, Gerhardt; Hayward, Nikki; Vidal, Laura; Spicer, James; Shaw, Heather M.; Bone, Elizabeth A.; Carter, Joanne; Hooftman, Leon; et al From Clinical Cancer Research (2009), 15(15), 4978-4985.
9. Tosedostat: aminopeptidase inhibitor oncolytic By Owen, R. T.; Castaner, R.; Bolos, J. From Drugs of the Future (2009), 34(2), 115-118.
10. Aminopeptidase inhibition as a targeted treatment strategy in myeloma By Moore, Hannah E.; Davenport, Emma L.; Smith, Emma M.; Muralikrishnan, Srikanth; Dunlop, Alan S.; Walker, Brian A.; Krige, David; Drummond, Alan H.; Hooftman, Leon; Morgan, Gareth J.; et al From Molecular Cancer Therapeutics (2009), 8(4), 762-770.
11. Dosing schedules of leukotriene synthesis inhibitors for human therapy By Hermann, David J.; Hartman, Daniel L.; Van Ess, Peter James; Wang, Wenping From PCT Int. Appl. (2008), WO 2009002746 A1 20081231.
12. CHR-2797: An Antiproliferative Aminopeptidase Inhibitor that Leads to Amino Acid Deprivation in Human Leukemic Cells By Krige, David; Needham, Lindsey A.; Bawden, Lindsay J.; Flores, Nicolas; Farmer, Hannah; Miles, Lauren E. C.; Stone, Erica; Callaghan, Juliana; Chandler, Stephen; Clark, Vanessa L.; et al From Cancer Research (2008), 68(16), 6669-6679.
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17. Aminopeptidase N (CD13) as a target for cancer chemotherapy By Wickstrom Malin; Larsson Rolf; Nygren Peter; Gullbo Joachim From Cancer science (2011), 102(3), 501-8.