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Anti-diabetic drugs
Alrestatin
Другие языки:

    Alrestatin

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    Alrestatin
    Alrestatin.svg
    Names
    Preferred IUPAC name
    (1,3-Dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid
    Identifiers
    3D model (JSmol)
    ChEMBL
    ChemSpider
    KEGG
    PubChem CID
    UNII
    • InChI=1S/C14H9NO4/c16-11(17)7-15-13(18)9-5-1-3-8-4-2-6-10(12(8)9)14(15)19/h1-6H,7H2,(H,16,17)
      Key: GCUCIFQCGJIRNT-UHFFFAOYSA-N
    • InChI=1/C14H9NO4/c16-11(17)7-15-13(18)9-5-1-3-8-4-2-6-10(12(8)9)14(15)19/h1-6H,7H2,(H,16,17)
      Key: GCUCIFQCGJIRNT-UHFFFAOYAQ
    • C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)CC(=O)O
    Properties
    C14H9NO4
    Molar mass 255.229 g·mol−1
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    Alrestatin is an inhibitor of aldose reductase, an enzyme involved in the pathogenesis of complications of diabetes mellitus, including diabetic neuropathy.

    Alrestat was first synthesized in 1969 and was the first aldose reductase inhibitor (ARI) with oral bioavailability to undergo clinical trials, in the late 1970s and early 1980s. Low-quality trials and a high incidence of adverse effects (particularly hepatotoxicity) led to termination of its development, and it was never in clinical use. It is structurally related to tolrestat, another ARI that was briefly marketed before being withdrawn in 1997.

    Synthesis

    Alrestatin can be synthesized by the reaction of 1,8-naphthoic anhydride with glycine.

    Alrestatin synthesis

    See also


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