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    Aspacytarabine [INN]

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Aspacytarabine, Aspacytarabine [inn], Bst-236, Aspacytarabine [usan], Jl7v54z2br, 2098942-53-9
    Molecular Formula
    C13H18N4O8
    Molecular Weight
    358.30  g/mol
    InChI Key
    PVPJTBAEAQVTPN-HRAQMCAYSA-N
    FDA UNII
    JL7V54Z2BR
    Aspacytarabine is a small molecule pro-drug consisting of cytarabine, an antimetabolite analog of cytidine with a modified arabinose sugar moiety, covalently bonded to asparagine, with potential antineoplastic activity. Upon intravenous administration, aspacytarabine targets cancer cells, which often lack asparagine synthetase and are dependent on an external source of amino acids due to their high metabolic rate. Once the prodrug is inside target cells, the cytarabine component is cleaved and competes with cytidine for incorporation into DNA. The arabinose sugar moiety of cytarabine sterically hinders the rotation of the molecule within DNA, resulting in cell cycle arrest, specifically during the S phase of replication. Cytarabine also inhibits DNA polymerase, resulting in a decrease in DNA replication and repair. Because BST-236 specifically targets cancer cells, it may spare normal tissues from cytarabine-related toxicities.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-amino-4-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-4-oxobutanoic acid
    2.1.2 InChI
    InChI=1S/C13H18N4O8/c14-5(12(22)23)3-8(19)15-7-1-2-17(13(24)16-7)11-10(21)9(20)6(4-18)25-11/h1-2,5-6,9-11,18,20-21H,3-4,14H2,(H,22,23)(H,15,16,19,24)/t5-,6+,9+,10-,11+/m0/s1
    2.1.3 InChI Key
    PVPJTBAEAQVTPN-HRAQMCAYSA-N
    2.1.4 Canonical SMILES
    C1=CN(C(=O)N=C1NC(=O)CC(C(=O)O)N)C2C(C(C(O2)CO)O)O
    2.1.5 Isomeric SMILES
    C1=CN(C(=O)N=C1NC(=O)C[C@@H](C(=O)O)N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    JL7V54Z2BR
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Aspacytarabine

    2. Aspacytarabine [inn]

    3. Bst-236

    4. Aspacytarabine [usan]

    5. Jl7v54z2br

    6. 2098942-53-9

    7. Unii-jl7v54z2br

    8. Aspacytarabine [who-dd]

    9. Chembl4297599

    10. Who 10941

    11. L-asparagine, N-(1-.beta.-d-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-

    12. L-asparagine, N-(1-beta-d-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-

    13. N4-(1-.beta.-d-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin-4-yl)-l-asparagine

    14. N4-(1-n2-d-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin-4-yl)- L-asparagine

    2.4 Create Date
    2018-12-16
    3 Chemical and Physical Properties
    Molecular Weight 358.30 g/mol
    Molecular Formula C13H18N4O8
    XLogP3-4.5
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count6
    Exact Mass358.11246355 g/mol
    Monoisotopic Mass358.11246355 g/mol
    Topological Polar Surface Area195 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity621
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1