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    Razuprotafib

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 1008510-37-9, Akb-9778, Razuprotafib [inn], Razuprotafib [usan], 0wax4ut396, Razuprotafib (usan)
    Molecular Formula
    C26H26N4O6S3
    Molecular Weight
    586.7  g/mol
    InChI Key
    KWJDHELCGJFUHW-SFTDATJTSA-N
    FDA UNII
    0WAX4UT396
    Razuprotafib is a small molecule inhibitor of vascular endothelial protein tyrosine phosphatase (VE-PTP), with potential vasculature stabilizing activity. Upon administration, razuprotafib targets, binds to and inhibits VE-PTP, which is a negative regulator of the endothelial cell (EC)-specific receptor tyrosine kinase (RTK) Tie2. This restores Tie2 activation, which may improve endothelial function and stabilize blood vessels. VE-PTP is upregulated in stressed endothelium associated with a variety of diseases. Tie2 plays an important role in endothelial function and vascular stability. A decrease in Tie2 activation leads to vascular leakage and inflammation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [4-[(2S)-2-[[(2S)-2-(methoxycarbonylamino)-3-phenylpropanoyl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid
    2.1.2 InChI
    InChI=1S/C26H26N4O6S3/c1-36-26(32)29-21(15-17-6-3-2-4-7-17)24(31)27-20(22-16-38-25(28-22)23-8-5-13-37-23)14-18-9-11-19(12-10-18)30-39(33,34)35/h2-13,16,20-21,30H,14-15H2,1H3,(H,27,31)(H,29,32)(H,33,34,35)/t20-,21-/m0/s1
    2.1.3 InChI Key
    KWJDHELCGJFUHW-SFTDATJTSA-N
    2.1.4 Canonical SMILES
    COC(=O)NC(CC1=CC=CC=C1)C(=O)NC(CC2=CC=C(C=C2)NS(=O)(=O)O)C3=CSC(=N3)C4=CC=CS4
    2.1.5 Isomeric SMILES
    COC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC2=CC=C(C=C2)NS(=O)(=O)O)C3=CSC(=N3)C4=CC=CS4
    2.2 Other Identifiers
    2.2.1 UNII
    0WAX4UT396
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Akb-9778

    2.3.2 Depositor-Supplied Synonyms

    1. 1008510-37-9

    2. Akb-9778

    3. Razuprotafib [inn]

    4. Razuprotafib [usan]

    5. 0wax4ut396

    6. Razuprotafib (usan)

    7. [4-[(2s)-2-[[(2s)-2-(methoxycarbonylamino)-3-phenylpropanoyl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic Acid

    8. Carbamic Acid, N-((1s)-2-oxo-1-(phenylmethyl)-2-(((1s)-2-(4-(sulfoamino)phenyl)-1-(2-(2-thienyl)-4-thiazolyl)ethyl)amino)ethyl)-, C-methyl Ester

    9. N-(4-{(2s)-2-{(2s)-2-[(methoxycarbonyl)amino]-3-phenylpropanamido}-2-[2-(thiophen-2-yl)-1,3-thiazol-4-yl]ethyl}phenyl)sulfamic Acid

    10. Razuprotafib [usan:inn]

    11. Unii-0wax4ut396

    12. Razuprotafib [who-dd]

    13. Schembl679459

    14. Chembl3931971

    15. Gtpl11336

    16. Akb9778

    17. Bdbm359124

    18. Us10220048, Compound Aa34

    19. Who 10271

    20. Compound Aa34 [us10220048]

    21. At18581

    22. Hy-109041

    23. Cs-0031483

    24. D11540

    25. N-(4-((2s)-2-((2s)-2-((methoxycarbonyl)amino)- 3-phenylpropanamido)-2-(2-(thiophen-2-yl)-1,3-thiazol4-yl)ethyl)phenyl)sulfamic Acid

    2.4 Create Date
    2010-07-26
    3 Chemical and Physical Properties
    Molecular Weight 586.7 g/mol
    Molecular Formula C26H26N4O6S3
    XLogP33.7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count12
    Exact Mass586.10144808 g/mol
    Monoisotopic Mass586.10144808 g/mol
    Topological Polar Surface Area212 Ų
    Heavy Atom Count39
    Formal Charge0
    Complexity906
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Mechanism of Action

    Razuprotafib inhibits [VE-PTP](https://go.drugbank.com/bio_entities/BE0003769) (a negative regulator of Tie2 in diseased blood vessels) by binding and inhibiting the intracellular catalytic domain of VE-PTP that inactivates Tie2. This in turn allows razuprotafib to restore Tie2 activation to allow for enhancement of endothelial function and stabilization of blood vessels. Razuprotafib is being investigated against diabetic vascular complications and acute respiratory distress syndrome (ARDS) in COVID-19.