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    Burixafor

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    2D Structure
    Also known as: Burixafor [inn], 1191448-17-5, Tg-0054, 2g17y0q20g, Phosphonic acid, p-(2-(4-(6-amino-2-(((trans-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)-4-pyrimidinyl)-1-piperazinyl)ethyl)-, (2-(4-(6-amino-2-((((1r,4r)-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl)phosphonic acid
    Molecular Formula
    C27H51N8O3P
    Molecular Weight
    566.7  g/mol
    InChI Key
    QLVSJMZJSABWRX-UHFFFAOYSA-N
    FDA UNII
    2G17Y0Q20G
    Burixafor is an orally bioavailable inhibitor of CXC chemokine receptor 4 (CXCR4) with receptor binding and hematopoietic stem cell-mobilization activities. Burixafor binds to the chemokine receptor CXCR4, thereby preventing the binding of stromal derived factor-1 (SDF-1 or CXCL12) to the CXCR4 receptor and subsequent receptor activation; this may induce the mobilization of hematopoietic stem and progenitor cells from the bone marrow into blood. CXCR4, a chemokine receptor belonging to the G protein-coupled receptor (GPCR) gene family, plays an important role in chemotaxis and angiogenesis and is upregulated in several tumor cell types; CXCL12/CXCR4 interaction induces retention of hematopoietic cells in the bone marrow.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[4-[6-amino-2-[[4-[[3-(cyclohexylamino)propylamino]methyl]cyclohexyl]methylamino]pyrimidin-4-yl]piperazin-1-yl]ethylphosphonic acid
    2.1.2 InChI
    InChI=1S/C27H51N8O3P/c28-25-19-26(35-15-13-34(14-16-35)17-18-39(36,37)38)33-27(32-25)31-21-23-9-7-22(8-10-23)20-29-11-4-12-30-24-5-2-1-3-6-24/h19,22-24,29-30H,1-18,20-21H2,(H2,36,37,38)(H3,28,31,32,33)
    2.1.3 InChI Key
    QLVSJMZJSABWRX-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CCC(CC1)NCCCNCC2CCC(CC2)CNC3=NC(=CC(=N3)N4CCN(CC4)CCP(=O)(O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    2G17Y0Q20G
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Burixafor [inn]

    2. 1191448-17-5

    3. Tg-0054

    4. 2g17y0q20g

    5. Phosphonic Acid, P-(2-(4-(6-amino-2-(((trans-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)-4-pyrimidinyl)-1-piperazinyl)ethyl)-

    6. (2-(4-(6-amino-2-((((1r,4r)-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl)phosphonic Acid

    7. Unii-2g17y0q20g

    8. Burixafor [who-dd]

    9. Chembl3545224

    10. Schembl13332861

    11. Schembl13354165

    12. Schembl13354172

    13. Schembl14693228

    14. Schembl14693238

    15. Tg0054

    16. Db11970

    17. Sb17205

    18. Tg 0054

    19. A857839

    20. Q27254687

    21. 2-[4-[6-amino-2-[[4-[[3-(cyclohexylamino)propylamino]methyl]cyclohexyl]methylamino]pyrimidin-4-yl]piperazin-1-yl]ethylphosphonic Acid

    2.4 Create Date
    2009-12-15
    3 Chemical and Physical Properties
    Molecular Weight 566.7 g/mol
    Molecular Formula C27H51N8O3P
    XLogP3-0.1
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count14
    Exact Mass566.38217452 g/mol
    Monoisotopic Mass566.38217452 g/mol
    Topological Polar Surface Area152 Ų
    Heavy Atom Count39
    Formal Charge0
    Complexity724
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1