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    4-Chlorokynurenine

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 153152-32-0, L-4-chlorokynurenine, Av-101, L-4-cl-kyn, 77xlh9l40b, 4-chloro kynurenine
    Molecular Formula
    C10H11ClN2O3
    Molecular Weight
    242.66  g/mol
    InChI Key
    HQLHZNDJQSRKDT-QMMMGPOBSA-N
    FDA UNII
    77XLH9L40B
    L-4-chlorokynurenine is an orally bioavailable, blood brain barrier (BBB) penetrating, chlorinated analog of the endogenous neuromodulator kynurenic acid and prodrug of 7-chlorokynurenic acid (7-Cl-KYNA), a N-methyl-D-aspartate receptor (NMDA-R) antagonist at the glycine-coagonist (GlyB) site, with potential anti-hyperalgesic, neuroprotective and anti-epileptic activities. Unlike 7-Cl-KYNA, L-4-chlorokynurenine, upon oral administration, crosses the BBB and is enzymatically converted, through transamination, within activated astrocytes located at sites of injury in the central nervous system (CNS) to its active metabolite, 7-Cl-KYNA, which allows for high levels of this active metabolite at these specific sites. In turn, 7-Cl-KYNA selectively binds to and blocks the GlyB site within the NMDA receptors. This inhibits both NMDA-R overstimulation by the excitatory neurotransmitter glutamate and NMDA-R-mediated excitotoxicity, which prevents neuronal damage and induces analgesia. In addition, another metabolite, 4-chloro-3-hydroxyanthranilic acid, inhibits the synthesis of quinolinic acid, an endogenous NMDA receptor agonist, thereby further preventing excitotoxic damage. Compared to conventional NMDA-R antagonists, NMDA-R GlyB-specific antagonists appear to have fewer side effects.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid
    2.1.2 InChI
    InChI=1S/C10H11ClN2O3/c11-5-1-2-6(7(12)3-5)9(14)4-8(13)10(15)16/h1-3,8H,4,12-13H2,(H,15,16)/t8-/m0/s1
    2.1.3 InChI Key
    HQLHZNDJQSRKDT-QMMMGPOBSA-N
    2.1.4 Canonical SMILES
    C1=CC(=C(C=C1Cl)N)C(=O)CC(C(=O)O)N
    2.1.5 Isomeric SMILES
    C1=CC(=C(C=C1Cl)N)C(=O)C[C@@H](C(=O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    77XLH9L40B
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 153152-32-0

    2. L-4-chlorokynurenine

    3. Av-101

    4. L-4-cl-kyn

    5. 77xlh9l40b

    6. 4-chloro Kynurenine

    7. J578.071c

    8. (s)-2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic Acid

    9. 4-cl-kyn

    10. (s)-4-chlorokynurenine

    11. 4-chloro-l-kynurenine

    12. Starbld0018860

    13. Unii-77xlh9l40b

    14. Schembl727370

    15. 3-(4-chloroanthraniloyl)alanine

    16. Zinc6092007

    17. Db12878

    18. Benzenebutanoic Acid, Alpha,2-diamino-4-chloro-gamma-oxo-, (s)

    19. Benzenebutanoic Acid, .alpha.,2-diamino-4-chloro-.gamma.-oxo-, (s)

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 242.66 g/mol
    Molecular Formula C10H11ClN2O3
    XLogP3-1.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass242.0458199 g/mol
    Monoisotopic Mass242.0458199 g/mol
    Topological Polar Surface Area106 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity285
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1