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    Tosedostat

    PharmaCompass
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    2D Structure
    Also known as: 238750-77-1, Chr 2797, Chr-2797, Tosedostat (chr2797), Kzk563j2uw, Unii-kzk563j2uw
    Molecular Formula
    C21H30N2O6
    Molecular Weight
    406.5  g/mol
    InChI Key
    FWFGIHPGRQZWIW-SQNIBIBYSA-N
    FDA UNII
    KZK563J2UW
    Tosedostat is a proprietary orally bioavailable inhibitor of the M1 family of aminopeptidases with potential antineoplastic activity. Aminopeptidase inhibitor CHR-2797 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. Noxa is a member of the BH3 (Bcl-2 homology 3)-only subgroup of the proapoptotic Bcl-2 (B-cell CLL/lymphoma 2) protein family.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    cyclopentyl (2S)-2-[[(2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]amino]-2-phenylacetate
    2.1.2 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
    2.1.3 InChI Key
    FWFGIHPGRQZWIW-SQNIBIBYSA-N
    2.1.4 Canonical SMILES
    CC(C)CC(C(C(=O)NO)O)C(=O)NC(C1=CC=CC=C1)C(=O)OC2CCCC2
    2.1.5 Isomeric SMILES
    CC(C)C[C@H]([C@@H](C(=O)NO)O)C(=O)N[C@@H](C1=CC=CC=C1)C(=O)OC2CCCC2
    2.2 Other Identifiers
    2.2.1 UNII
    KZK563J2UW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(2-(hydroxy(hydroxycarbamoyl)methyl)-4-methylpentanoylamino)-2-phenylethanoic Acid Cyclopentyl Ester

    2. Chr 2797

    3. Chr-2797

    4. Chr2797

    2.3.2 Depositor-Supplied Synonyms

    1. 238750-77-1

    2. Chr 2797

    3. Chr-2797

    4. Tosedostat (chr2797)

    5. Kzk563j2uw

    6. Unii-kzk563j2uw

    7. (s)-cyclopentyl 2-((r)-2-((s)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4-methylpentanamido)-2-phenylacetate

    8. Cyclopentyl (s)-2-((r)-2-((s)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4-methylpentanamido)-2-phenylacetate

    9. Tosedostat [inn]

    10. Tosedostat [usan:inn]

    11. Bb-76163

    12. Tosedostat (usan/inn)

    13. Tosedostat [usan]

    14. Chr-2797(tosedostat)

    15. Chr-2797; Tosedostat

    16. Chr2797 - Tosedostat

    17. Tosedostat [who-dd]

    18. Mls006011104

    19. Chembl2103847

    20. Schembl19236550

    21. Chebi:95044

    22. Dtxsid60178577

    23. Bcpp000283

    24. Hms3414a15

    25. Hms3678a15

    26. Cyclopentyl (2s)-2-[[(2r)-2-[(1s)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]amino]-2-phenylacetate

    27. Ex-a2628

    28. Bdbm50277143

    29. Nsc806020

    30. Zinc13914293

    31. Akos024457707

    32. At25061

    33. Bcp9000524

    34. Db11781

    35. Nsc-806020

    36. Ncgc00263175-01

    37. Ac-35830

    38. As-55983

    39. Hy-14807

    40. Smr004676647

    41. Cs-0003570

    42. D10026

    43. 750t771

    44. A857789

    45. Brd-k92241597-001-01-1

    46. Q27166812

    47. Alpha-[[(2r)-2-[(1s)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]amino]benzeneacetic Acid Cyclopentyl Ester

    48. Benzeneacetic Acid, .alpha.-(((2r)-2-((1s)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4- Methyl-1-oxopenty)lamino)-, Cyclopentyl Ester, (.alpha.s)-

    49. Benzeneacetic Acid, Alpha-(((2r)-2-((1s)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4-methyl-1-oxopentyl)amino)-, Cyclopentyl Ester, (alphas)-

    50. Cyclopentyl (2s)-2-((2r)-2-((1s)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4- Methylpentanamido)-2-phenylacetate

    2.4 Create Date
    2007-02-10
    3 Chemical and Physical Properties
    Molecular Weight 406.5 g/mol
    Molecular Formula C21H30N2O6
    XLogP32.3
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count10
    Exact Mass406.21038668 g/mol
    Monoisotopic Mass406.21038668 g/mol
    Topological Polar Surface Area125 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity555
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Pharmacology

    Tosedostat has pleiotropic effects against a range of human tumor cell lines originating from diverse tumor types in vitro and in vivo.

    4.2 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    4.3 Mechanism of Action

    Tosedostat is anti-proliferative agent which induces apoptosis in leukemic cell lines in vitro. The mechanism underlying these anti-cancer actions is unclear, particularly since normal cells are much less sensitive to the agents than transformed cells. It exerts potent anti-proliferative, pro-apoptotic and anti-angiogenic effects in vitro and shows selectivity for transformed over non-transformed cells. It inhibits a number of M1 aminopeptidase enzyme family members in vitro (eg puromycin-sensitive aminopeptidase (PSA), leukotriene A4 hydrolase (LTA4H)).