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Fidarestat

CAS No.:
136087-85-9
Catalog Number:
AG01DQ0Z
Molecular Formula:
C12H10FN3O4
Molecular Weight:
279.2239
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$144
- +
5mg
99%
1 week
United States
$411
- +
10mg
99%
1 week
United States
$710
- +
Product Description
Catalog Number:
AG01DQ0Z
Chemical Name:
Fidarestat
CAS Number:
136087-85-9
Molecular Formula:
C12H10FN3O4
Molecular Weight:
279.2239
MDL Number:
MFCD00919183
IUPAC Name:
(2S,4S)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide
InChI:
InChI=1S/C12H10FN3O4/c13-5-1-2-7-6(3-5)12(4-8(20-7)9(14)17)10(18)15-11(19)16-12/h1-3,8H,4H2,(H2,14,17)(H2,15,16,18,19)/t8-,12-/m0/s1
InChI Key:
WAAPEIZFCHNLKK-UFBFGSQYSA-N
SMILES:
O=C1NC(=O)[C@]2(N1)C[C@H](Oc1c2cc(F)cc1)C(=O)N
UNII:
8SH8T1164U
Properties
Complexity:
485  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
279.066g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
279.227g/mol
Monoisotopic Mass:
279.066g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
111A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3  
Literature
Title Journal
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
Prevention of VEGF-induced growth and tube formation in human retinal endothelial cells by aldose reductase inhibition. Journal of diabetes and its complications 20120901
Interplay of sorbitol pathway of glucose metabolism, 12/15-lipoxygenase, and mitogen-activated protein kinases in the pathogenesis of diabetic peripheral neuropathy. Biochemical pharmacology 20120401
Amelioration of acute kidney injury in lipopolysaccharide-induced systemic inflammatory response syndrome by an aldose reductase inhibitor, fidarestat. PloS one 20120101
Amelioration of experimental autoimmune uveoretinitis by aldose reductase inhibition in Lewis rats. Investigative ophthalmology & visual science 20111001
Aldose reductase deficiency protects from autoimmune- and endotoxin-induced uveitis in mice. Investigative ophthalmology & visual science 20111001
Inhibition of aldose reductase prevents colon cancer metastasis. Carcinogenesis 20110801
Aldose reductase inhibition prevents hypoxia-induced increase in hypoxia-inducible factor-1alpha (HIF-1alpha) and vascular endothelial growth factor (VEGF) by regulating 26 S proteasome-mediated protein degradation in human colon cancer cells. The Journal of biological chemistry 20110708
Design and synthesis of potent and selective aldose reductase inhibitors based on pyridylthiadiazine scaffold. European journal of medicinal chemistry 20110501
Inhibition of aldose reductase prevents angiogenesis in vitro and in vivo. Angiogenesis 20110501
Aldose reductase deficiency in mice protects from ragweed pollen extract (RWE)-induced allergic asthma. Respiratory research 20110101
Evaluation of the aldose reductase inhibitor fidarestat on ischemia-reperfusion injury in rat retina. International journal of molecular medicine 20100701
Aldose reductase inhibitor ameliorates renal vascular endothelial growth factor expression in streptozotocin-induced diabetic rats. Yonsei medical journal 20100501
The role of the polyol pathway in acute kidney injury caused by hindlimb ischaemia in mice. The Journal of pathology 20100401
Aldose reductase inhibitor fidarestat attenuates leukocyte-endothelial interactions in experimental diabetic rat retina in vivo. Current eye research 20100201
Aldose reductase inhibitors in the treatment of diabetic peripheral neuropathy: a review. Journal of diabetes and its complications 20100101
Aldose reductase inhibition prevents metaplasia of airway epithelial cells. PloS one 20100101
Docking and molecular dynamics studies toward the binding of new natural phenolic marine inhibitors and aldose reductase. Journal of molecular graphics & modelling 20090901
Charge density and electrostatic interactions of fidarestat, an inhibitor of human aldose reductase. Journal of the American Chemical Society 20090812
[Pathophysiology and treatment for diabetic neuropathy]. Rinsho shinkeigaku = Clinical neurology 20090401
Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress. Chemico-biological interactions 20090316
Prevention of posterior capsular opacification through aldose reductase inhibition. Investigative ophthalmology & visual science 20090201
The aldose reductase inhibitor fidarestat suppresses ischemia-reperfusion-induced inflammatory response in rat retina. Pharmacology 20090101
Aldose reductase inhibitor fidarestat counteracts diabetes-associated cataract formation, retinal oxidative-nitrosative stress, glial activation, and apoptosis. International journal of molecular medicine 20080601
Unusual binding mode of the 2S4R stereoisomer of the potent aldose reductase cyclic imide inhibitor fidarestat (2S4S) in the 15 K crystal structure of the ternary complex refined at 0.78 A resolution: implications for the inhibition mechanism. Journal of medicinal chemistry 20080313
Gene deletion and pharmacological inhibition of aldose reductase protect against retinal ischemic injury. Experimental eye research 20071101
High-fat diet induced neuropathy of pre-diabetes and obesity: effects of 'healthy' diet and aldose reductase inhibition. Diabetes 20071001
Fidarestat improves cardiomyocyte contractile function in db/db diabetic obese mice through a histone deacetylase Sir2-dependent mechanism. Journal of hypertension 20071001
Deletion of aldose reductase leads to protection against cerebral ischemic injury. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20070801
Selectivity determinants of the aldose and aldehyde reductase inhibitor-binding sites. Cellular and molecular life sciences : CMLS 20070801
Effects of fidarestat, an aldose reductase inhibitor, on nerve conduction velocity and bladder function in streptozotocin-treated female rats. Journal of diabetes and its complications 20070101
Effect of the aldose reductase inhibitor fidarestat on experimental diabetic neuropathy in the rat. Diabetologia 20061201
The role of polyol pathway in high glucose-induced endothelial cell damages. Diabetes research and clinical practice 20060901
High glucose-induced activation of the polyol pathway and changes of gene expression profiles in immortalized adult mouse Schwann cells IMS32. Journal of neurochemistry 20060701
Factorizing selectivity determinants of inhibitor binding toward aldose and aldehyde reductases: structural and thermodynamic properties of the aldose reductase mutant Leu300Pro-fidarestat complex. Journal of medicinal chemistry 20050908
Structure of aldehyde reductase holoenzyme in complex with the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity. Journal of medicinal chemistry 20050825
[Progress on the drug therapy for diabetic microangiopathies: aldose reductase inhibitor]. Nihon rinsho. Japanese journal of clinical medicine 20050601
[Role of aldose reductase in the progression of diabetic retinopathies]. Nihon rinsho. Japanese journal of clinical medicine 20050601
Aldose reductase inhibition counteracts oxidative-nitrosative stress and poly(ADP-ribose) polymerase activation in tissue sites for diabetes complications. Diabetes 20050101
Effects of polyol pathway hyperactivity on protein kinase C activity, nociceptive peptide expression, and neuronal structure in dorsal root ganglia in diabetic mice. Diabetes 20041201
High-resolution structures of human aldose reductase holoenzyme in complex with stereoisomers of the potent inhibitor Fidarestat: stereospecific interaction between the enzyme and a cyclic imide type inhibitor. Journal of medicinal chemistry 20040826
Mitogen-activated protein kinase p38 mediates reduced nerve conduction velocity in experimental diabetic neuropathy: interactions with aldose reductase. Diabetes 20040701
Ultrahigh resolution drug design. II. Atomic resolution structures of human aldose reductase holoenzyme complexed with Fidarestat and Minalrestat: implications for the binding of cyclic imide inhibitors. Proteins 20040601
Suppression of 3-deoxyglucosone and heparin-binding epidermal growth factor-like growth factor mRNA expression by an aldose reductase inhibitor in rat vascular smooth muscle cells. Biochemical and biophysical research communications 20040206
Effect of fidarestat and alpha-lipoic acid on diabetes-induced epineurial arteriole vascular dysfunction. Experimental diabesity research 20040101
Erythrocytic sorbitol contents in diabetic patients correlate with blood aldose reductase protein contents and plasma glucose levels, and are normalized by the potent aldose reductase inhibitor fidarestat (SNK-860). Journal of diabetes and its complications 20040101
[The inhibitory effect of aldose reductase inhibitor for proliferation in the lens epithelial cells of rat sugar cataract]. Nippon Ganka Gakkai zasshi 20031001
Fidarestat. Sanwa Kagaku/NC Curex/Sankyo. Current opinion in investigational drugs (London, England : 2000) 20031001
Apoptotic cell death in the lens epithelium of rat sugar cataract. Experimental eye research 20030701
Aldose reductase inhibitor fidarestat prevents retinal oxidative stress and vascular endothelial growth factor overexpression in streptozotocin-diabetic rats. Diabetes 20030301
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
Long-term treatment with fidarestat suppresses the development of diabetic retinopathy in STZ-induced diabetic rats. Journal of diabetes and its complications 20030101
Sorbitol dehydrogenase overexpression potentiates glucose toxicity to cultured retinal pericytes. Biochemical and biophysical research communications 20021129
[Fidarestat (SNK-860)]. Nihon rinsho. Japanese journal of clinical medicine 20020901
Fidarestat (SNK-860), a potent aldose reductase inhibitor, normalizes the elevated sorbitol accumulation in erythrocytes of diabetic patients. Journal of diabetes and its complications 20020101
Fidarestat. Aldos, SK 860, SNK 860. Drugs in R&D 20020101
Aldose reductase inhibitors. Journal of enzyme inhibition 20011201
Clinical efficacy of fidarestat, a novel aldose reductase inhibitor, for diabetic peripheral neuropathy: a 52-week multicenter placebo-controlled double-blind parallel group study. Diabetes care 20011001
Pharmacological properties of fidarestat, a potent aldose reductase inhibitor, clarified by using sorbitol in human and rat erythrocytes. Pharmacology 20010501
A potent aldose reductase inhibitor, (2S,4S)-6-fluoro-2', 5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide (Fidarestat): its absolute configuration and interactions with the aldose reductase by X-ray crystallography. Journal of medicinal chemistry 20000615
Properties