Alrestatin

Alrestatin
Names
IUPAC name
(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid
Identifiers
51876-97-2
3D model (Jmol) Interactive image
ChEMBL ChEMBL63055
ChemSpider 2036
PubChem 2120
Properties
C14H9NO4
Molar mass 255.226
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

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in clinical use.[3][4] It is structurally related to tolrestat, another ARI that was briefly marketed before being withdrawn in 1997.

Synthesis

Alrestatin can be synthesized by the reaction of naphthoic anhydride with glycine.[5]

Alrestatin synthesis

1,8-Naphthoic anhydride de:Naphthalsäureanhydrid

See also

References

  1. ↑ Gabbay KH, Spack N, Loo S, Hirsch HJ, Ackil AA (April 1979). "Aldose reductase inhibition: studies with alrestatin". Metab Clin Exp. 28 (4 Suppl 1): 471–6. doi:10.1016/0026-0495(79)90059-3. PMID 122298.
  2. ↑ Ehrig T, Bohren KM, Prendergast FG, Gabbay KH (June 1994). "Mechanism of aldose reductase inhibition: binding of NADP+/NADPH and alrestatin-like inhibitors". Biochemistry. 33 (23): 7157–65. doi:10.1021/bi00189a019. PMID 8003482.
  3. ↑ Striker, Gary E.; Gueriguian, John L. (1991). Diabetic complications: epidemiology and pathogenetic mechanisms. New York: Raven Press. pp. 293–4. ISBN 0-88167-648-9.
  4. ↑ Veves, Aristidis (2007). "Aldose reductase inhibitors for the treatment of diabetic neuropathy". In Rayaz A., Malik; Veves, Aristidis. Diabetic Neuropathy: Clinical Management. Totowa, NJ: Humana Press. pp. 309–11. ISBN 1-59745-311-0. Retrieved 2013-02-13.
  5. ↑ Ayerst Mckenna & Harrison, U.S. Patent 3,821,383


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