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82964-04-3,MFCD00864170
Catalog No.:AA00G3NI

82964-04-3 | Tolrestat

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1mg
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5mg
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$166.00   $116.00
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10mg
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$306.00   $214.00
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25mg
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50mg
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100mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00G3NI
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
Properties
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  

Downstream Synthesis Route

[1]Lee;Lee[JournalofPharmaceuticalSciences,1990,vol.79,#7,p.628-633]

[1]Lee;Lee[JournalofPharmaceuticalSciences,1990,vol.79,#7,p.628-633]

[1]Lee;Lee[JournalofPharmaceuticalSciences,1990,vol.79,#7,p.628-633]

[1]Lee;Lee[JournalofPharmaceuticalSciences,1990,vol.79,#7,p.628-633]

[1]Lee;Lee[JournalofPharmaceuticalSciences,1990,vol.79,#7,p.628-633]

Literature

Title: 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.

Journal: Chemico-biological interactions 20130225

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

Journal: Experimental eye research 20120801

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

Journal: Journal of computer-aided molecular design 20120201

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

Journal: Frontiers in pharmacology 20120101

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

Journal: PloS one 20120101

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

Journal: Frontiers in pharmacology 20120101

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

Journal: Computational and mathematical methods in medicine 20120101

Title: Reductive metabolism increases the proinflammatory activity of aldehyde phospholipids.

Journal: Journal of lipid research 20111201

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

Journal: PLoS computational biology 20111201

Title: Structure of aldose reductase from Giardia lamblia.

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

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

Journal: Journal of periodontology 20110601

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

Journal: Journal of natural products 20110527

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

Journal: Diabetologia 20110501

Title: Systematic exploitation of multiple receptor conformations for virtual ligand screening.

Journal: PloS one 20110101

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

Journal: PloS one 20110101

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

Journal: Respiratory research 20110101

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

Journal: Experimental diabetes research 20110101

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

Journal: Diabetes care 20101201

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

Journal: Diabetes care 20101201

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

Journal: Drug metabolism and disposition: the biological fate of chemicals 20101201

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

Journal: Yonsei medical journal 20100501

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

Journal: Bioorganic & medicinal chemistry 20100401

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

Journal: European journal of medicinal chemistry 20100301

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

Journal: Biological & pharmaceutical bulletin 20100101

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

Journal: Biological & pharmaceutical bulletin 20100101

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

Journal: Clinical ophthalmology (Auckland, N.Z.) 20100101

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

Journal: Diabetes 20091101

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

Journal: Circulation research 20091009

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

Journal: Journal of molecular graphics & modelling 20090901

Title: Elevated triglycerides correlate with progression of diabetic neuropathy.

Journal: Diabetes 20090701

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

Journal: Archives of biochemistry and biophysics 20090701

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

Journal: Chemico-biological interactions 20090316

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

Journal: Journal of biochemistry 20090201

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

Journal: Bioorganic & medicinal chemistry 20090201

Title: The cycle of genome-directed medicine.

Journal: Genome medicine 20090101

Title: Advances in pharmacological strategies for the prevention of cataract development.

Journal: Indian journal of ophthalmology 20090101

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

Journal: Diabetic medicine : a journal of the British Diabetic Association 20080701

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

Journal: Journal of molecular biology 20080620

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

Journal: Journal of medicinal chemistry 20080612

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

Journal: The Journal of biological chemistry 20080404

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

Journal: Experimental diabetes research 20080101

Title: Diabetic retinopathy: an update.

Journal: Indian journal of ophthalmology 20080101

Title: C-Peptide effects on renal physiology and diabetes.

Journal: Experimental diabetes research 20080101

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

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

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

Journal: Vascular health and risk management 20071201

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

Journal: Journal of molecular biology 20071109

Title: Aldose reductase inhibitors for the treatment of diabetic polyneuropathy.

Journal: The Cochrane database of systematic reviews 20071017

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

Journal: Endocrinology 20070901

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

Journal: Journal of molecular biology 20070525

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

Journal: Chemistry Central journal 20070101

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

Journal: Investigative ophthalmology & visual science 20061201

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

Journal: Cytokine 20061101

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

Journal: Journal of molecular biology 20061013

Title: Phenolic marine natural products as aldose reductase inhibitors.

Journal: Journal of natural products 20061001

Title: Assessment of basic indirect pharmacodynamic response models with physiological limits.

Journal: Journal of pharmacokinetics and pharmacodynamics 20060401

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

Journal: Diabetes 20060401

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

Journal: Journal of molecular biology 20060210

Title: 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: Journal of medicinal chemistry 20050505

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

Journal: Endocrine reviews 20050501

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

Journal: Diabetes 20050301

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

Journal: Bioorganic & medicinal chemistry 20050117

Title: Aldose reductase-catalyzed reduction of aldehyde phospholipids.

Journal: The Journal of biological chemistry 20041217

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

Journal: Diabetes 20041101

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

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

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

Journal: FEBS letters 20040716

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

Journal: Journal of medicinal chemistry 20031218

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

Journal: Journal of medicinal chemistry 20031120

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

Journal: The Biochemical journal 20030801

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

Journal: Journal of medicinal chemistry 20030410

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

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

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

Journal: Chemico-biological interactions 20030201

Title: Aldose reductase mediates the mitogenic signals of cytokines.

Journal: Chemico-biological interactions 20030201

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

Journal: Chemico-biological interactions 20030201

Title: 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: Journal of medicinal chemistry 20030130

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

Journal: Diabetes 20021001

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

Journal: Circulation research 20020809

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

Journal: Bioorganic & medicinal chemistry 20020401

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

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

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

Journal: Diabetes, obesity & metabolism 20020101

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

Journal: Journal of medicinal chemistry 20011206

Title: Aldose reductase inhibitors.

Journal: Journal of enzyme inhibition 20011201

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

Journal: Atherosclerosis 20011001

Title: Involvement of aldose reductase in the metabolism of atherogenic aldehydes.

Journal: Chemico-biological interactions 20010130

Title: Regulation of vascular smooth muscle cell growth by aldose reductase.

Journal: Chemico-biological interactions 20010130

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

Journal: Journal of medicinal chemistry 20000323

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

Journal: Journal of medicinal chemistry 19850701

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

Journal: Journal of medicinal chemistry 19840301

Title: Sestanj K, et al. N--(trifluoromethyl)-6-methoxy-1-naphthalenylthioxomethyl- N-methylglycine (Tolrestat), a potent, orally active aldose reductase inhibitor. J Med Chem. 1984 Mar;27(3):255-6.

Title: Simard-Duquesne N, et al. The effects of a new aldose reductase inhibitor (tolrestat) in galactosemic and diabetic rats. Metabolism. 1985 Oct;34(10):885-92.

Title: Srivastava S, et al. Aldose reductase protects against early atherosclerotic lesion formation in apolipoprotein E-null mice. Circ Res. 2009 Oct 9;105(8):793-802.

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