{{Chembox | ImageFile = Alrestatin.svg | ImageClass = skin-invert-image | ImageSize = 160px | ImageAlt = | PIN = (1,3-Dioxo-1''H''-benzo[''de'']isoquinolin-2(3''H'')-yl)acetic acid | OtherNames = |Section1={{Chembox Identifiers | CASNo = 51411-04-2 | PubChem = 2120 | ChemSpiderID = 2036 | ChEMBL = 63055 | UNII = 515DHK15LG | KEGG = D02835 | SMILES = C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)CC(=O)O | 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) | InChIKey = GCUCIFQCGJIRNT-UHFFFAOYAQ | StdInChI = 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) | StdInChIKey = GCUCIFQCGJIRNT-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=14 | H=9 | N=1 | O=4 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Alrestatin''' is an inhibitor of aldose reductase, an enzyme involved in the pathogenesis of complications of diabetes mellitus, including diabetic neuropathy.<ref>{{cite journal |vauthors=Gabbay KH, Spack N, Loo S, Hirsch HJ, Ackil AA |title=Aldose reductase inhibition: studies with alrestatin |journal=Metab Clin Exp |volume=28 |issue=4 Suppl 1 |pages=471–6 |date=April 1979 |pmid=122298 |doi=10.1016/0026-0495(79)90059-3}}</ref><ref>{{cite journal |vauthors=Ehrig T, Bohren KM, Prendergast FG, Gabbay KH |title=Mechanism of aldose reductase inhibition: binding of NADP+/NADPH and alrestatin-like inhibitors |journal=Biochemistry |volume=33 |issue=23 |pages=7157–65 |date=June 1994 |pmid=8003482 |doi= 10.1021/bi00189a019}}</ref>
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.<ref>{{cite book |author1=Striker, Gary E. |author2=Gueriguian, John L. |title=Diabetic complications: epidemiology and pathogenetic mechanisms |publisher=Raven Press |location=New York |year=1991 |pages=293–4 |isbn=0-88167-648-9}}</ref><ref>{{cite book |author =Veves, Aristidis |editor1=Rayaz A., Malik |editor2=Veves, Aristidis |title=Diabetic Neuropathy: Clinical Management |chapter=Aldose reductase inhibitors for the treatment of diabetic neuropathy |publisher=Humana Press |location=Totowa, NJ |year=2007 |pages=309–11 |isbn=978-1-59745-311-0 |chapter-url=https://books.google.com/books?id=dMKoFySox7kC&pg=PA310 |access-date=2013-02-13}}</ref> 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 naphthalic anhydride with glycine.<ref>Ayerst Mckenna & Harrison, {{US patent|3,821,383}}</ref> thumb|center|500px|Alrestatin synthesis
==See also== *Amonafide * Scriptaid
==References== {{reflist}}
Category:Experimental diabetes drugs Category:Imides Category:Carboxylic acids