Tosedostat
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MedKoo CAT#: 205648

CAS#: 238750-77-1

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.


Chemical Structure

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Tosedostat
CAS# 238750-77-1

Theoretical Analysis

MedKoo Cat#: 205648
Name: Tosedostat
CAS#: 238750-77-1
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

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 850.0 Same day
200.0mg USD 1650.0 Same day
500.0mg USD 2650.0 Same day
1.0g USD 3750.0 2 Weeks
2.0g USD 5650.0 2 Weeks
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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

Preparing Stock Solutions

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.

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

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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.

5. Surface topographies for non-toxic bioadhesion control By Brennan, Anthony B.; Long, Christopher James; Bagan, Joseph W.; Schumacher, James Frederick; Spiecker, Mark M. From U.S. Pat. Appl. Publ. (2010), US 20100226943 A1 20100909.

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.

13. Preparation of cytostatic hydroxamic acid derivatives of amino acids By Pearson, Lindsey Ann; Ayscough, Andrew Paul; Huxley, Philip; Drummond, Alan From U.S. (2002), US 6462023 B1 20021008.

14. Antibacterial hydroxamic acid derivatives By Hunter, Michael George; Beckett, Raymond Paul; Clements, Martin John; Whittaker, Mark From PCT Int. Appl. (2000), WO 2000044373 A1 20000803.

15. Hydroxamic acid derivatives as inhibitors of beta-amyloid production By Johnstone, Mandy; Ayscough, Andrew Paul From PCT Int. Appl. (2000), WO 2000009119 A1 20000224.

16. Hydroxamic acid derivatives of amino acids as antiinflammatories By Ayscough, Andrew Paul; Whittaker, Mark From PCT Int. Appl. (1999), WO 9940910 A1 19990819.

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.



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