82964-04-3 | Tolrestat

Packsize	Purity	Availability	Price	Discounted Price
1mg	≥98%	in stock	$42.00	$29.00
5mg	≥98%	in stock	$150.00	$105.00
10mg	≥98%	in stock	$276.00	$193.00
25mg	≥98%	in stock	$587.00	$411.00
50mg	≥98%	in stock	$1,148.00	$804.00
100mg	≥98%	in stock	$1,797.00	$1,258.00

Description

• Catalog Number: AH51130
• Chemical Name: Tolrestat
• CAS Number: 82964-04-3
• Molecular Formula: C16H14F3NO3S
• Molecular Weight: 357.3475
• MDL Number: MFCD00864170
• SMILES: COc1ccc2c(c1C(F)(F)F)cccc2C(=S)N(CC(=O)O)C

Computed Properties

• Complexity: 486
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 24
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 4
• XLogP3: 3.7

Literature

• X-ray structure of the V301L aldo-keto reductase 1B10 complexed with NADP(+) and the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity.

  Chemico-biological interactions 20130225

• Osmotic stress, not aldose reductase activity, directly induces growth factors and MAPK signaling changes during sugar cataract formation.

  Experimental eye research 20120801

• The good, the bad and the twisted: a survey of ligand geometry in protein crystal structures.

  Journal of computer-aided molecular design 20120201

• Aldo-Keto Reductase 1B10 and Its Role in Proliferation Capacity of Drug-Resistant Cancers.

  Frontiers in pharmacology 20120101

• The isolation and characterization of β-glucogallin as a novel aldose reductase inhibitor from Emblica officinalis.

  PloS one 20120101

• Biological role of aldo-keto reductases in retinoic Acid biosynthesis and signaling.

  Frontiers in pharmacology 20120101

• Implication of crystal water molecules in inhibitor binding at ALR2 active site.

  Computational and mathematical methods in medicine 20120101

• Reductive metabolism increases the proinflammatory activity of aldehyde phospholipids.

  Journal of lipid research 20111201

• Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

  PLoS computational biology 20111201

• Structure of aldose reductase from Giardia lamblia.

  Acta crystallographica. Section F, Structural biology and crystallization communications 20110901

• Efficacy of structurally diverse aldose reductase inhibitors on experimental periodontitis in rats.

  Journal of periodontology 20110601

• Selective inhibition of the tumor marker aldo-keto reductase family member 1B10 by oleanolic acid.

  Journal of natural products 20110527

• Genetic deficiency of aldose reductase counteracts the development of diabetic nephropathy in C57BL/6 mice.

  Diabetologia 20110501

• Systematic exploitation of multiple receptor conformations for virtual ligand screening.

  PloS one 20110101

• Increased recruitment but impaired function of leukocytes during inflammation in mouse models of type 1 and type 2 diabetes.

  PloS one 20110101

• Aldose reductase deficiency in mice protects from ragweed pollen extract (RWE)-induced allergic asthma.

  Respiratory research 20110101

• Osmolarity and glucose differentially regulate aldose reductase activity in cultured mouse podocytes.

  Experimental diabetes research 20110101

• Diabetic neuropathy: a cross-sectional study of the relationships among tests of neurophysiology.

  Diabetes care 20101201

• Low peripheral nerve conduction velocities and amplitudes are strongly related to diabetic microvascular complications in type 1 diabetes: the EURODIAB Prospective Complications Study.

  Diabetes care 20101201

• A predictive ligand-based Bayesian model for human drug-induced liver injury.

  Drug metabolism and disposition: the biological fate of chemicals 20101201

• Aldose reductase inhibitor ameliorates renal vascular endothelial growth factor expression in streptozotocin-induced diabetic rats.

  Yonsei medical journal 20100501

• Chromene-3-carboxamide derivatives discovered from virtual screening as potent inhibitors of the tumour maker, AKR1B10.

  Bioorganic & medicinal chemistry 20100401

• Synthesis and biological evaluation of [1,2,4]triazino[4,3-a] benzimidazole acetic acid derivatives as selective aldose reductase inhibitors.

  European journal of medicinal chemistry 20100301

• Selective inhibition of the tumor marker AKR1B10 by antiinflammatory N-phenylanthranilic acids and glycyrrhetic acid.

  Biological & pharmaceutical bulletin 20100101

• Rat aldose reductase-like protein (AKR1B14) efficiently reduces the lipid peroxidation product 4-oxo-2-nonenal.

  Biological & pharmaceutical bulletin 20100101

• Prevention of diabetic eye disease: the commonest cause of blindness in individuals younger than 65 years.

  Clinical ophthalmology (Auckland, N.Z.) 20100101

• Reductive metabolism of AGE precursors: a metabolic route for preventing AGE accumulation in cardiovascular tissue.

  Diabetes 20091101

• Aldose reductase protects against early atherosclerotic lesion formation in apolipoprotein E-null mice.

  Circulation research 20091009

• Docking and molecular dynamics studies toward the binding of new natural phenolic marine inhibitors and aldose reductase.

  Journal of molecular graphics & modelling 20090901

• Elevated triglycerides correlate with progression of diabetic neuropathy.

  Diabetes 20090701

• Kinetic studies of AKR1B10, human aldose reductase-like protein: endogenous substrates and inhibition by steroids.

  Archives of biochemistry and biophysics 20090701

• Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress.

  Chemico-biological interactions 20090316

• Prostaglandin F2alpha synthase activities of aldo-keto reductase 1B1, 1B3 and 1B7.

  Journal of biochemistry 20090201

• Correlation of binding constants and molecular modelling of inhibitors in the active sites of aldose reductase and aldehyde reductase.

  Bioorganic & medicinal chemistry 20090201

• The cycle of genome-directed medicine.

  Genome medicine 20090101

• Advances in pharmacological strategies for the prevention of cataract development.

  Indian journal of ophthalmology 20090101

• Stratified analyses for selecting appropriate target patients with diabetic peripheral neuropathy for long-term treatment with an aldose reductase inhibitor, epalrestat.

  Diabetic medicine : a journal of the British Diabetic Association 20080701

• Merging the binding sites of aldose and aldehyde reductase for detection of inhibitor selectivity-determining features.

  Journal of molecular biology 20080620

• Acetic acid aldose reductase inhibitors bearing a five-membered heterocyclic core with potent topical activity in a visual impairment rat model.

  Journal of medicinal chemistry 20080612

• Role of nitric oxide in regulating aldose reductase activation in the ischemic heart.

  The Journal of biological chemistry 20080404

• Effect of C-peptide on diabetic neuropathy in patients with type 1 diabetes.

  Experimental diabetes research 20080101

• Diabetic retinopathy: an update.

  Indian journal of ophthalmology 20080101

• C-Peptide effects on renal physiology and diabetes.

  Experimental diabetes research 20080101

• Structural basis for the high all-trans-retinaldehyde reductase activity of the tumor marker AKR1B10.

  Proceedings of the National Academy of Sciences of the United States of America 20071226

• Current concepts in targeted therapies for the pathophysiology of diabetic microvascular complications.

  Vascular health and risk management 20071201

• Tracing changes in protonation: a prerequisite to factorize thermodynamic data of inhibitor binding to aldose reductase.

  Journal of molecular biology 20071109

• Aldose reductase inhibitors for the treatment of diabetic polyneuropathy.

  The Cochrane database of systematic reviews 20071017

• Aldose reductase-regulated tumor necrosis factor-alpha production is essential for high glucose-induced vascular smooth muscle cell growth.

  Endocrinology 20070901

• Evidence for a novel binding site conformer of aldose reductase in ligand-bound state.

  Journal of molecular biology 20070525

• PocketPicker: analysis of ligand binding-sites with shape descriptors.

  Chemistry Central journal 20070101

• Inhibition of aldose reductase prevents lipopolysaccharide-induced inflammatory response in human lens epithelial cells.

  Investigative ophthalmology & visual science 20061201

• Mediation of aldose reductase in lipopolysaccharide-induced inflammatory signals in mouse peritoneal macrophages.

  Cytokine 20061101

• Expect the unexpected or caveat for drug designers: multiple structure determinations using aldose reductase crystals treated under varying soaking and co-crystallisation conditions.

  Journal of molecular biology 20061013

• Phenolic marine natural products as aldose reductase inhibitors.

  Journal of natural products 20061001

• Assessment of basic indirect pharmacodynamic response models with physiological limits.

  Journal of pharmacokinetics and pharmacodynamics 20060401

• Contribution of aldose reductase to diabetic hyperproliferation of vascular smooth muscle cells.

  Diabetes 20060401

• High-resolution crystal structure of aldose reductase complexed with the novel sulfonyl-pyridazinone inhibitor exhibiting an alternative active site anchoring group.

  Journal of molecular biology 20060210

• 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.

  Journal of medicinal chemistry 20050505

• Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options.

  Endocrine reviews 20050501

• Requirement of aldose reductase for the hyperglycemic activation of protein kinase C and formation of diacylglycerol in vascular smooth muscle cells.

  Diabetes 20050301

• Spirohydantoin derivatives of thiopyrano[2,3-b]pyridin-4(4H)-one as potent in vitro and in vivo aldose reductase inhibitors.

  Bioorganic & medicinal chemistry 20050117

• Aldose reductase-catalyzed reduction of aldehyde phospholipids.

  The Journal of biological chemistry 20041217

• Activation of nuclear factor-kappaB by hyperglycemia in vascular smooth muscle cells is regulated by aldose reductase.

  Diabetes 20041101

• Inhibition of aldose reductase attenuates TNF-alpha-induced expression of adhesion molecules in endothelial cells.

  FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20040801

• Aldose reductase regulates TNF-alpha-induced cell signaling and apoptosis in vascular endothelial cells.

  FEBS letters 20040716

• Rational design of an indolebutanoic acid derivative as a novel aldose reductase inhibitor based on docking and 3D QSAR studies of phenethylamine derivatives.

  Journal of medicinal chemistry 20031218

• Synthesis, activity, and molecular modeling studies of novel human aldose reductase inhibitors based on a marine natural product.

  Journal of medicinal chemistry 20031120

• Human aldose reductase and human small intestine aldose reductase are efficient retinal reductases: consequences for retinoid metabolism.

  The Biochemical journal 20030801

• Novel, highly potent aldose reductase inhibitors: cyano(2-oxo-2,3-dihydroindol-3-yl)acetic acid derivatives.

  Journal of medicinal chemistry 20030410

• Aldose reductase mediates cytotoxic signals of hyperglycemia and TNF-alpha in human lens epithelial cells.

  FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030201

• Hydrogen bonding interactions between aldose reductase complexed with NADP(H) and inhibitor tolrestat studied by molecular dynamics simulations and binding assay.

  Chemico-biological interactions 20030201

• Aldose reductase mediates the mitogenic signals of cytokines.

  Chemico-biological interactions 20030201

• Role of aldose reductase in TNF-alpha-induced apoptosis of vascular endothelial cells.

  Chemico-biological interactions 20030201

• Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversible modification of proteins from monosaccharides.

  Journal of medicinal chemistry 20030130

• Nitric oxide prevents aldose reductase activation and sorbitol accumulation during diabetes.

  Diabetes 20021001

• Aldose reductase is an obligatory mediator of the late phase of ischemic preconditioning.

  Circulation research 20020809

• Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones.

  Bioorganic & medicinal chemistry 20020401

• Pathogenesis of diabetic neuropathy--do hyperglycemia and aldose reductase inhibitors affect neuroactive steroid formation in the rat sciatic nerves?

  Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association 20020101

• Effects of aminoguanidine and tolrestat on the development of ocular and renal structural changes in experimental diabetic rats.

  Diabetes, obesity & metabolism 20020101

• [1,2,4]Triazino[4,3-a]benzimidazole acetic acid derivatives: a new class of selective aldose reductase inhibitors.

  Journal of medicinal chemistry 20011206

• Aldose reductase inhibitors.

  Journal of enzyme inhibition 20011201

• Identification of biochemical pathways for the metabolism of oxidized low-density lipoprotein derived aldehyde-4-hydroxy trans-2-nonenal in vascular smooth muscle cells.

  Atherosclerosis 20011001

• Involvement of aldose reductase in the metabolism of atherogenic aldehydes.

  Chemico-biological interactions 20010130

• Regulation of vascular smooth muscle cell growth by aldose reductase.

  Chemico-biological interactions 20010130

• Molecular modeling of the aldose reductase-inhibitor complex based on the X-ray crystal structure and studies with single-site-directed mutants.

  Journal of medicinal chemistry 20000323

• Aldose reductase inhibitors: a potential new class of agents for the pharmacological control of certain diabetic complications.

  Journal of medicinal chemistry 19850701

• N-[5-(trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]- N-methylglycine (Tolrestat), a potent, orally active aldose reductase inhibitor.

  Journal of medicinal chemistry 19840301