Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H12F3N3O3S |
| Molecular Weight | 419.377 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1=NN(CC2=NC3=CC(=CC=C3S2)C(F)(F)F)C(=O)C4=CC=CC=C14
InChI
InChIKey=BCSVCWVQNOXFGL-UHFFFAOYSA-N
InChI=1S/C19H12F3N3O3S/c20-19(21,22)10-5-6-15-14(7-10)23-16(29-15)9-25-18(28)12-4-2-1-3-11(12)13(24-25)8-17(26)27/h1-7H,8-9H2,(H,26,27)
Zopolrestat is a novel carboxylic acid aldose reductase inhibitor. It has been shown to normalize sorbitol, fructose, and myoinositol levels in sciatic nerve, lens, retina, and kidney in diabetic rats and to restore normal renal plasma flow in galactosemic rats. It is being evaluated as an aldose reductase inhibitor for the treatment of diabetic complications.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Aldose reductase activation is a key component of myocardial response to ischemia. | 2002 Feb |
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| Hyperglycemia increases endothelial superoxide that impairs smooth muscle cell Na+-K+-ATPase activity. | 2002 Mar |
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| Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversible modification of proteins from monosaccharides. | 2003 Jan 30 |
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| Aldose reductase induced by hyperosmotic stress mediates cardiomyocyte apoptosis: differential effects of sorbitol and mannitol. | 2003 Oct 3 |
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| Interaction between the polyol pathway and non-enzymatic glycation on aortic smooth muscle cell migration and monocyte adhesion. | 2004 Dec 10 |
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| Effects of inhibition of the polyol pathway during chronic peritoneal exposure to a dialysis solution. | 2005 Feb |
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| [Effects of aldose reductase on the transforming growth factor-beta1-induced expression of fibronectin and collagen IV: experiment with cultured rat mesangial cells]. | 2005 Jul 13 |
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| [Effects of aldose reductase on the expression of fibronectin and collagen IV in cultured rat renal mesangial cells]. | 2005 Mar |
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| Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options. | 2005 May |
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| Aldose reductase pathway mediates JAK-STAT signaling: a novel axis in myocardial ischemic injury. | 2005 May |
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| Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications. | 2005 May 5 |
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| Aldose reductase regulates TGF-beta1-induced production of fibronectin and type IV collagen in cultured rat mesangial cells. | 2006 Apr |
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| Mediation of aldose reductase in lipopolysaccharide-induced inflammatory signals in mouse peritoneal macrophages. | 2006 Nov |
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| Expect the unexpected or caveat for drug designers: multiple structure determinations using aldose reductase crystals treated under varying soaking and co-crystallisation conditions. | 2006 Oct 13 |
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| Aldose reductase inhibition prevents endotoxin-induced uveitis in rats. | 2007 Oct |
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| A 41-year-old man with polyarthritis and severe autonomic neuropathy. | 2008 Aug |
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| Endotoxin causes pulmonary hypertension by upregulating smooth muscle endothelin type-B receptors: role of aldose reductase. | 2008 Aug |
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| Inhibition of aldose reductase prevents experimental allergic airway inflammation in mice. | 2009 Aug 6 |
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| Cancer biomarker AKR1B10 and carbonyl metabolism. | 2009 Mar 16 |
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| Inhibition of aldose reductase prevents growth factor-induced G1-S phase transition through the AKT/phosphoinositide 3-kinase/E2F-1 pathway in human colon cancer cells. | 2010 Apr |
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| Polyol pathway impairs the function of SERCA and RyR in ischemic-reperfused rat hearts by increasing oxidative modifications of these proteins. | 2010 Jul |
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| Role of aldose reductase in the high glucose induced expression of fibronectin in human mesangial cells. | 2010 Jul |
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| [Effect of PKC signalling pathway and aldose reductase on expression of fibronectin induced by transforming growth factor-β1 in human mesangial cells]. | 2010 Jun |
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| Inhibition of aldose reductase attenuates endotoxin signals in human non-pigmented ciliary epithelial cells. | 2010 May |
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| Elevated Serum Sorbitol and not Fructose in Type 2 Diabetic Patients. | 2010 May 4 |
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| Aldose reductase and AGE-RAGE pathways: central roles in the pathogenesis of vascular dysfunction in aging rats. | 2010 Oct |
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| Aldose reductase inhibition suppresses airway inflammation. | 2011 May 30 |
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| Anti-neuroinflammatory efficacy of the aldose reductase inhibitor FMHM via phospholipase C/protein kinase C-dependent NF-κB and MAPK pathways. | 2013 Nov 15 |
Sample Use Guides
Hearts from acute diabetic (Type I) and age-matched control rats were isolated and retrogradely perfused. Hearts had either control perfusion or exposure to 1 microM zopolrestat for 10 min, followed by 20 min of global ischemia and 60 min of reperfusion. Zopolrestat blunted the rise in [Na]i during ischemia in both diabetic hearts and non-diabetic hearts. The end-ischemic [Na]i was 21.3 +/- 2.6 mM in the zopolrestat treated diabetics and 25.9 +/- 2.3 in zopolrestat treated non-diabetics, versus 31.6 +/- 2.6 mM and 32.9 +/- 2.8 mM in the untreated diabetics and untreated non-diabetics, respectively, (P = 0.002). Similarly, the rise in [Ca]i at the end of ischemia was significantly reduced in zopolrestat treated diabetic and non-diabetic hearts (P = 0.005). Zopolrestat increased the activity of Na-,K(+)-ATPase in diabetic hearts under baseline conditions (11.70 +/- 0.95 versus 7.28 +/- 0.98 mumol/h/mg protein, P = 0.005) as well as during ischemia and reperfusion. Similar changes in Na+,K(+)-ATPase activity were also observed in non-diabetic hearts.
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C72880
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ACTIVE MOIETY
