Alrestatin

Alrestatin is an inhibitor of aldose reductase, an enzyme involved in the pathogenesis of complications of diabetes mellitus, including diabetic neuropathy.^[1][2]

Quick facts Names, Identifiers ...

Alrestatin

Names
Preferred IUPAC name (1,3-Dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid
Identifiers
CAS Number	51411-04-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL63055
ChemSpider	2036
KEGG	D02835
PubChem CID	2120
UNII	515DHK15LG
CompTox Dashboard (EPA)	DTXSID7045655
InChI 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
SMILES C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)CC(=O)O
Properties
Chemical formula	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). Infobox references

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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in clinical use.^[3][4] It is structurally related to tolrestat, another ARI that was briefly marketed before being withdrawn in 1997.