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    Upamostat

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    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Upamostat, Upamostat [inn], 1191101-18-4, S5m7kw6u17, 1-piperazinecarboxylic acid, 4-((2s)-3-(3-((e)-amino(hydroxyimino)methyl)phenyl)-1-oxo-2-(((2,4,6-tris(1-methylethyl)phenyl)sulfonyl)amino)propyl)-, ethyl ester, Ethyl 4-((2s)-3-{3-((e)-n'-hydroxycarbamimidoyl)phenyl)-2-(2,3,5-tri(propan-2-yl)benzenesulfonamido)propanoyl)piperazine-1-carboxylate
    Molecular Formula
    C32H47N5O6S
    Molecular Weight
    629.8  g/mol
    InChI Key
    HUASEDVYRABWCV-NDEPHWFRSA-N
    FDA UNII
    S5M7KW6U17
    Upamostat is an orally bioavailable, 3-amidinophenylalanine-derived, second generation serine protease inhibitor prodrug targeting the human urokinase plasminogen activator (uPA) system with potential antineoplastic and antimetastatic activities. After oral administration, upamostat is converted to the active N alpha-(2,4,6-triisopropylphenylsulfonyl)-3-amidino-(L)-phenylalanine-4-ethoxycarbonylpiperazide (WX-UK1), which inhibits several serine proteases, particularly uPA; inhibition of uPA may result in the inhibition of tumor growth and metastasis. uPA is a serine protease involved in degradation of the extracellular matrix and tumor cell migration and proliferation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    ethyl 4-[(2S)-3-[3-[(E)-N'-hydroxycarbamimidoyl]phenyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanoyl]piperazine-1-carboxylate
    2.1.2 InChI
    InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34-40)35-44(41,42)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7/h9-11,16,18-22,28,35,40H,8,12-15,17H2,1-7H3,(H2,33,34)/t28-/m0/s1
    2.1.3 InChI Key
    HUASEDVYRABWCV-NDEPHWFRSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)N1CCN(CC1)C(=O)C(CC2=CC(=CC=C2)C(=NO)N)NS(=O)(=O)C3=C(C=C(C=C3C(C)C)C(C)C)C(C)C
    2.1.5 Isomeric SMILES
    CCOC(=O)N1CCN(CC1)C(=O)[C@H](CC2=CC(=CC=C2)/C(=N\O)/N)NS(=O)(=O)C3=C(C=C(C=C3C(C)C)C(C)C)C(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    S5M7KW6U17
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Rhb-107

    2. Upamostat

    3. Wx-671

    2.3.2 Depositor-Supplied Synonyms

    1. Upamostat

    2. Upamostat [inn]

    3. 1191101-18-4

    4. S5m7kw6u17

    5. 1-piperazinecarboxylic Acid, 4-((2s)-3-(3-((e)-amino(hydroxyimino)methyl)phenyl)-1-oxo-2-(((2,4,6-tris(1-methylethyl)phenyl)sulfonyl)amino)propyl)-, Ethyl Ester

    6. Ethyl 4-((2s)-3-{3-((e)-n'-hydroxycarbamimidoyl)phenyl)-2-(2,3,5-tri(propan-2-yl)benzenesulfonamido)propanoyl)piperazine-1-carboxylate

    7. Ethyl 4-[(2s)-3-[3-[(e)-n'-hydroxycarbamimidoyl]phenyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanoyl]piperazine-1-carboxylate

    8. Unii-s5m7kw6u17

    9. Wx-671

    10. Ethyl 4-((2s)-3-(3-((e)-n'-hydroxycarbamimidoyl)phenyl)-2-(2,3,5-tri(propan-2-yl)benzenesulfonamido)propanoyl)piperazine-1-carboxylate

    11. Upamostat [who-dd]

    12. Schembl12618906

    13. Schembl20669283

    14. 590368-25-5

    15. Ex-a6355

    16. Wx-671wx-671

    17. Db13052

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 629.8 g/mol
    Molecular Formula C32H47N5O6S
    XLogP35
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count12
    Exact Mass629.32470541 g/mol
    Monoisotopic Mass629.32470541 g/mol
    Topological Polar Surface Area163 Ų
    Heavy Atom Count44
    Formal Charge0
    Complexity1070
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1