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    Vecabrutinib

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: 1510829-06-7, Biib-062, Bsk-4841, Fp0182, Vecabrutinib [inn], Vecabrutinib [usan]
    Molecular Formula
    C22H24ClF4N7O2
    Molecular Weight
    529.9  g/mol
    InChI Key
    QLRRJMOBVVGXEJ-XHSDSOJGSA-N
    FDA UNII
    PQ7O0OB5GU
    Vecabrutinib is an orally available second-generation, reversible inhibitor of Bruton's tyrosine kinase (BTK; Bruton agammaglobulinemia tyrosine kinase), with potential antineoplastic activity. Upon administration, vecabrutinib non-covalently binds to and inhibits the activity of both wild-type and the C481S mutated form of BTK, a resistance mutation in the BTK active site in which cysteine is substituted for serine at residue 481. This prevents the activation of the B-cell antigen receptor (BCR) signaling pathway and BTK-mediated activation of downstream survival pathways. This leads to an inhibition of the growth of malignant B-cells that overexpress BTK. Compared to other BTK inhibitors, SNS-062 does not require interaction with the BTK C481 site and inhibits the proliferation of cells harboring the BTK C481S mutation. Other irreversible BTK inhibitors covalently bind to the C481 site to inhibit BTK's activity; the C481S mutation prevents that binding. BTK, a member of the Src-related BTK/Tec family of cytoplasmic tyrosine kinases, is overexpressed in B-cell malignancies; it plays an important role in the development, activation, signaling, proliferation and survival of B-lymphocytes.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3R,4S)-1-(6-amino-5-fluoropyrimidin-4-yl)-3-[(3R)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxopiperidin-1-yl]piperidine-4-carboxamide
    2.1.2 InChI
    InChI=1S/C22H24ClF4N7O2/c23-12-6-11(22(25,26)27)7-13(8-12)32-15-2-1-4-34(21(15)36)16-9-33(5-3-14(16)19(29)35)20-17(24)18(28)30-10-31-20/h6-8,10,14-16,32H,1-5,9H2,(H2,29,35)(H2,28,30,31)/t14-,15+,16-/m0/s1
    2.1.3 InChI Key
    QLRRJMOBVVGXEJ-XHSDSOJGSA-N
    2.1.4 Canonical SMILES
    C1CC(C(=O)N(C1)C2CN(CCC2C(=O)N)C3=NC=NC(=C3F)N)NC4=CC(=CC(=C4)C(F)(F)F)Cl
    2.1.5 Isomeric SMILES
    C1C[C@H](C(=O)N(C1)[C@H]2CN(CC[C@@H]2C(=O)N)C3=NC=NC(=C3F)N)NC4=CC(=CC(=C4)C(F)(F)F)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    PQ7O0OB5GU
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 1510829-06-7

    2. Biib-062

    3. Bsk-4841

    4. Fp0182

    5. Vecabrutinib [inn]

    6. Vecabrutinib [usan]

    7. Pq7o0ob5gu

    8. Fp-0182

    9. Sns062

    10. (3r,3'r,4's)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxo[1,3'-bipiperidine]-4'-carboxamide

    11. (3r,3'r,4's)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-2-oxo-(1,3'-bipiperidine)-4'-carboxamide

    12. (3r,3'r,4's)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-2-oxo-[1,3'-bipiperidine]-4'-carboxamide

    13. Unii-pq7o0ob5gu

    14. Vecabrutinib (usan/inn)

    15. Vecabrutinib [usan:inn]

    16. Biib062

    17. Vecabrutinib [who-dd]

    18. Chembl4297640

    19. Schembl16765727

    20. Gtpl10231

    21. Bcp29646

    22. Ex-a3159

    23. Bdbm50546200

    24. Fp-182

    25. Nsc810114

    26. Who 10643

    27. Zb1596

    28. Nsc-810114

    29. Ac-36339

    30. Hy-109078

    31. Cs-0033553

    32. D11428

    33. (1,3'-bipiperidine)-4'-carboxamide, 1'-(6-amino-5-fluoro-4-pyrimidinyl)-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-2-oxo-, (3r,3'r,4's)-

    34. (3r,4s)-1-(6-amino-5-fluoropyrimidin-4-yl)-3-[(3r)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxopiperidin-1-yl]piperidine-4-carboxamide

    2.4 Create Date
    2014-01-06
    3 Chemical and Physical Properties
    Molecular Weight 529.9 g/mol
    Molecular Formula C22H24ClF4N7O2
    XLogP32.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count5
    Exact Mass529.1616134 g/mol
    Monoisotopic Mass529.1616134 g/mol
    Topological Polar Surface Area131 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity809
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1