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    Marimastat

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 154039-60-8, Bb-2516, Bb 2516, Bb2516, D5eqv23tds, Nsc-719333
    Molecular Formula
    C15H29N3O5
    Molecular Weight
    331.41  g/mol
    InChI Key
    OCSMOTCMPXTDND-OUAUKWLOSA-N
    FDA UNII
    D5EQV23TDS
    a matrix metalloproteinase inhibitor active in patients with advanced carcinoma of the pancreas, prostate, or ovary
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N',3-dihydroxy-2-(2-methylpropyl)butanediamide
    2.1.2 InChI
    InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1
    2.1.3 InChI Key
    OCSMOTCMPXTDND-OUAUKWLOSA-N
    2.2 Other Identifiers
    2.2.1 UNII
    D5EQV23TDS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bb-2516

    2.3.2 Depositor-Supplied Synonyms

    1. 154039-60-8

    2. Bb-2516

    3. Bb 2516

    4. Bb2516

    5. D5eqv23tds

    6. Nsc-719333

    7. Gi5712

    8. Kb-r 8898

    9. Ta2516

    10. Gi-5712

    11. Ta-2516

    12. (2s,3r)-3-(((1s)-2,2-dimethyl-1-(methylcarbamoxy)propyl)carboyl)-2-hydroxy-5-methylhexanohydroxamic Acid

    13. Chebi:50662

    14. Dtxsid20165524

    15. Nsc689451

    16. Nsc719333

    17. Marimistat

    18. (2s,3r)-n-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-n',2-dihydroxy-3-(2-methylpropyl)butanediamide

    19. Marimastatum

    20. (2s,3r)-n-((1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl)-n',2-dihydroxy-3-(2-methylpropyl)butanediamide

    21. Refchem:810621

    22. Dtxcid3088015

    23. (2s,3r)-3-((s)-(2,2-dimethyl-1-(methylcarbamoyl) Propyl)carbamoyl)-2-hydroxy-5-methylhexanohydroxamic Acid

    24. Marimastat (bb-2516)

    25. (2r,3s)-n1-((s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-n4,3-dihydroxy-2-isobutylsuccinamide

    26. (2r,3s)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-n',3-dihydroxy-2-(2-methylpropyl)butanediamide

    27. Mfcd00866242

    28. Bb2516;ta2516

    29. Chembl279785

    30. Marimastat [usan]

    31. (2s,3r)-3-(((1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl)carbamoyl)-2-hydroxy-5-methylhexanohydroxamic Acid

    32. (2s,3r)-n(4)-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-n(1),2-dihydroxy-3-(2-methylpropyl)butanediamide

    33. (2r)-n-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-2-[(1s)-1-hydroxy-2-(hydroxyamino)-2-oxo-ethyl]-4-methyl-pentanamide

    34. (2s,3r)-n~4~-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-n~1~,2-dihydroxy-3-(2-methylpropyl)butanediamide

    35. Butanediamide, N4-((1s)-2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s,3r)-

    36. Butanediamide, N4-[(1s)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s,3r)-

    37. Smr002530328

    38. Marimastat (usan/inn)

    39. Unii-d5eqv23tds

    40. Marimastat [usan:inn:ban]

    41. (2s,3r)-3-[[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]carbamoyl]-2-hydroxy-5-methylhexanohydroxamic Acid

    42. Butaneamide,2-dimethyl-1-[(methylamino)carbonyl]propyl]- N1,2-dihydroxy-3-(2-methylpropyl)-, (2s,3r)-

    43. 3hy7

    44. Marimastat [mi]

    45. Marimastat [inn]

    46. D03795

    47. Marimastat [mart.]

    48. Marimastat [who-dd]

    49. Schembl34033

    50. Mls003899230

    51. Mls006010669

    52. Cid_119031

    53. Gtpl5220

    54. Orb1300377

    55. Marimastat, >=98% (hplc)

    56. Ex-a643

    57. Glxc-06760

    58. Bdbm50063917

    59. S7156

    60. Akos024457206

    61. Ccg-267821

    62. Cs-3456

    63. Db00786

    64. Gi 5712

    65. Nsc 719333

    66. Nsc-689451

    67. Ta 2516

    68. Marimastat - Cas 154039-60-8

    69. (2s,3r)-n'-[(1s)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-n,2-dihydroxy-3-(2-methylpropyl)butanediamide

    70. Ac-35828

    71. As-57129

    72. Butanediamide, N(sup 4)-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n(sup 1),2-dihydroxy-3-(2-methylpropyl)-, (2s-(n(sup 4)(r*),2r*,3s*))-

    73. Butanediamide, N4-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s-(n4(r*),2r*,3s*))-

    74. Fm161188

    75. Hy-12169

    76. Ns00068619

    77. Q6763659

    78. Brd-k21396683-001-04-8

    79. (2s,3r)-n4-[(1s)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-n1,2-dihydroxy-3-(2-methylpropyl)butanediamide;bb 2516;ta 2516

    80. Butanediamide, N(sup 4)-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-n1,2-dihydroxy-3-(2-methylpropyl)-, (2s-(n4(r*),2r*,3s*))-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 331.41 g/mol
    Molecular Formula C15H29N3O5
    XLogP30.5
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count8
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area128
    Heavy Atom Count23
    Formal Charge0
    Complexity431
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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

    For the treatment of various cancers

    5 Pharmacology and Biochemistry
    5.1 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.

    5.2 Mechanism of Action

    Marimastat is a broad spectrum matrix metalloprotease inhibitor. It mimics the peptide structure of natural MMP substrates and binds to matrix metalloproteases, thereby preventing the degradation of the basement membrane by these proteases. This antiprotease action prevents the migration of endothelial cells needed to form new blood vessels. Inhibition of MMPs also prevents the entry and exit of tumor cells into existing blood cells, thereby preventing metastasis.

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