loader
Please Wait
Applying Filters...

AbbVie Contract Manufacturing AbbVie Contract Manufacturing

X
menu

    Market Place

    Market Place

    Post Enquiry

    Post Enquiry
    menu

    Technical details about Upamostat, learn more about the structure, uses, toxicity, action, side effects and more

    Client Email Product
    Menu

    Upamostat

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass

    Biopharma Group offers CDMO services with expertise in contract R&D for dried products & liquid formulations.

    Rochem, your partner in developing, sourcing, and supplying pharmaceutical & animal health ingredients of Chinese origin.

    2D Structure
    1. 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
    Post Enquiry
    POST ENQUIRY