SML0527
Epalrestat
≥98% (HPLC)
Synonym(s):
(5Z)-5-[(2E)-2-Methyl-3-phenyl-2-propen-1-ylidene]-4-oxo-2-thioxo-3-thiazolidineacetic acid
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About This Item
Empirical Formula (Hill Notation):
C15H13NO3S2
CAS Number:
Molecular Weight:
319.40
UNSPSC Code:
12352200
NACRES:
NA.77
Quality Level
Assay
≥98% (HPLC)
form
powder
storage condition
protect from light
color
yellow to orange
solubility
DMSO: 5 mg/mL, clear (warmed)
storage temp.
−20°C
SMILES string
S1\C(=C/C(=C/c2ccccc2)/C)\C(=O)N(C1=S)CC(=O)O
InChI
1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8-
InChI key
CHNUOJQWGUIOLD-NFZZJPOKSA-N
Related Categories
Application
Epalrestat has been used as an aldose reductase inhibitor:
- in the dahomey larvae diet fed forDrosophila
- for non-irradiated and X-ray irradiated human aldose reductase
- to test its protective effect in mice with bleomycin-induced pulmonary fibrosis
Biochem/physiol Actions
Epalrestat inhibits Aldose Reductase (AR) involved in the rate limiting step in the conversion of glucose to sorbitol under hyperglycemic conditions. Aldose reductase has been the target of multiple clinical investigatons to treat diabetic neuropathy and retinopathy. Epalrestat is an approved drug in Japan and India, used for the treatment of diabetic neuropathy.
Epalrestat is an Aldose Reductase inhibitor.
Features and Benefits
This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Other Notes
Light sensitve
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Hyun Ah Jung et al.
The Journal of pharmacy and pharmacology, 60(9), 1227-1236 (2008-08-23)
Important targets for the prevention and treatment of diabetic complications include aldose reductase (AR) inhibitors (ARIs) and inhibitors of advanced glycation endproduct (AGE) formation. Here we evaluate the inhibitory activities of prenylated flavonoids isolated from Sophora flavescens, a traditional herbal
Juan Gu et al.
Journal of ethnopharmacology, 133(1), 6-13 (2010-09-08)
To investigate the effects of lignans extracted from Eucommia ulmoides and epalrestat on vascular remodeling in spontaneously hypertensive rats. Ten-week-old male spontaneously hypertensive rats were randomly divided into 3 groups (12 rats each group), and treated orally with 100 mg/kg/d
J W Steele et al.
Drugs & aging, 3(6), 532-555 (1993-11-01)
Epalrestat is a carboxylic acid derivative which inhibits aldose reductase, an enzyme of the sorbitol (polyol) pathway. Under hyperglycaemic conditions epalrestat reduces intracellular sorbitol accumulation, which has been implicated in the pathogenesis of late-onset complications of diabetes mellitus. Epalrestat 150
Mary Ann Ramirez et al.
Pharmacotherapy, 28(5), 646-655 (2008-05-02)
Diabetic neuropathy is one of the most common long-term complications in patients with diabetes mellitus, with a prevalence of 60-70% in the United States. Treatment options include antidepressants, anticonvulsants, tramadol, and capsaicin. These agents are modestly effective for symptomatic relief
Feyzi Sinan Tokalı et al.
Drug development research, 83(3), 586-604 (2021-09-30)
A series of novel sulfonates containing quinazolin-4(3H)-one ring derivatives was designed to inhibit aldose reductase (ALR2, EC 1.1.1.21). Novel quinazolinone derivatives (1-21) were synthesized from the reaction of sulfonated aldehydes with 3-amino-2-alkylquinazolin-4(3H)-ones in glacial acetic acid with good yields (85%-94%).
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