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    Marizomib

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: Salinosporamide a, 437742-34-2, Npi-0052, (-)-salinosporamide a, Npi 0052, Ml 858
    Molecular Formula
    C15H20ClNO4
    Molecular Weight
    313.77  g/mol
    InChI Key
    NGWSFRIPKNWYAO-SHTIJGAHSA-N
    FDA UNII
    703P9YDP7F
    Marizomib is a naturally-occurring salinosporamide, isolated from the marine actinomycete Salinospora tropica, with potential antineoplastic activity. Marizomib irreversibly binds to and inhibits the 20S catalytic core subunit of the proteasome by covalently modifying its active site threonine residues; inhibition of ubiquitin-proteasome mediated proteolysis results in an accumulation of poly-ubiquitinated proteins, which may result in the disruption of cellular processes, cell cycle arrest, the induction of apoptosis, and the inhibition of tumor growth and angiogenesis. This agent more may more potent and selective than the proteasome inhibitor bortezomib.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
    2.1.2 InChI
    InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1
    2.1.3 InChI Key
    NGWSFRIPKNWYAO-SHTIJGAHSA-N
    2.1.4 Canonical SMILES
    CC12C(C(=O)NC1(C(=O)O2)C(C3CCCC=C3)O)CCCl
    2.1.5 Isomeric SMILES
    C[C@]12[C@H](C(=O)N[C@]1(C(=O)O2)[C@H]([C@H]3CCCC=C3)O)CCCl
    2.2 Other Identifiers
    2.2.1 UNII
    703P9YDP7F
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Homosalinosporamide A

    2. Npi 0052

    3. Npi-0052

    4. Salinosporamide A

    2.3.2 Depositor-Supplied Synonyms

    1. Salinosporamide A

    2. 437742-34-2

    3. Npi-0052

    4. (-)-salinosporamide A

    5. Npi 0052

    6. Ml 858

    7. Salinosporamide A (npi-0052, Marizomib)

    8. 703p9ydp7f

    9. Chebi:48045

    10. (1r,4r,5s)-4-(2-chloroethyl)-1-((s)-((s)-cyclohex-2-en-1-yl)(hydroxy)methyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

    11. (1r,4r,5s)-4-(2-chloroethyl)-1-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

    12. Marizomib [usan:inn]

    13. Marizomibum

    14. Unii-703p9ydp7f

    15. Homosalinosporamide A

    16. Marizomib [inn]

    17. Marizomib (usan/inn)

    18. Marizomib [usan]

    19. Marizomib [who-dd]

    20. Schembl151667

    21. Salinosporamide A [mi]

    22. Chembl371405

    23. Dtxsid00904019

    24. (1s,2r,5r)-2-(2-chloroethyl)-5-[(s)-[(1s)-cyclohex-2-en-1-yl]-hydroxymethyl]-1-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione

    25. Ex-a3259

    26. Zinc3990364

    27. Bdbm50398608

    28. Akos027323566

    29. Db11762

    30. Hy-10985

    31. Cs-0002986

    32. D09640

    33. A872651

    34. Q7404722

    35. (1r,4r,5s)-4-(2-chloroethyl)-1-((s)-((1s)-cyclohex-2-en-1-yl)hydroxymethyl)-5-methyl- 6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione

    36. (1r,4r,5s)-4-(2-chloroethyl)-1-((s)-((s)-cyclohex-2-enyl)(hydroxy)methyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

    37. (1r,4r,5s)-4-(2-chloroethyl)-1-[(s)-[(1s)-cyclohex-2-en-1-yl]-hydroxymethyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

    38. 6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione, 4-(2-chloroethyl)-1-((s)-(1s)-2-cyclohexen-1-ylhydroxymethyl)-5-methyl-, (1r,4r,5s)-

    39. 6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione, 4-(2-chloroethyl)-1-((s)-(1s)-2-cyclohexen-1-ylhydroxymethyl)-5-methyl-, (1r,4r,5s)-

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 313.77 g/mol
    Molecular Formula C15H20ClNO4
    XLogP31.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass313.1080858 g/mol
    Monoisotopic Mass313.1080858 g/mol
    Topological Polar Surface Area75.6 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity508
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of malignant glial tumours