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Epalrestat

Epalrestat structure

CAS No:
82159-09-9
Formula:
C15H13NO3S2
Chemical Name:
Epalrestat
Synonyms:
3-Thiazolidineacetic acid,5-[(2E)-2-methyl-3-phenyl-2-propen-1-ylidene]-4-oxo-2-thioxo-,(5Z)-;3-Thiazolidineacetic acid,5-(2-methyl-3-phenyl-2-propenylidene)-4-oxo-2-thioxo-,(Z,E)-;3-Thiazolidineacetic acid,5-[(2E)-2-methyl-3-phenyl-2-propenylidene]-4-oxo-2-thioxo-,(5Z)-;(5Z)-5-[(2E)-2-Methyl-3-phenyl-2-propen-1-ylidene]-4-oxo-2-thioxo-3-thiazolidineacetic acid;ONO 2235;Epalrestat;Kinedak;Sorbistat;Eabeth;2-[(Z)-5-((E)-2-Methyl-3-phenylallylidene)-4-oxo-2-thioxothiazolidin-3-yl]acetic acid;125654-73-1
Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System

Description

Epalrestat is an aldose reductase inhibitor for the treatment of diabetic neuropathy.Target: Aldose ReductaseEpalrestat may affect or delay progression of the underlying disease process. Data from six clinical trials were evaluated, and it was determined that epalrestat 50 mg 3 times/day may improve motor and sensory nerve conduction velocity and subjective neuropathy symptoms as compared with baseline and placebo. Epalrestat may serve as a new therapeutic option to prevent or slow the p

Epalrestat is a monocarboxylic acid that is 1,3-thiazolidine which is substituted on the nitrogen by a carboxymethyl group, at positions 2 and 4 by thioxo and oxo groups, respectively, and at position 5 by a 2-methyl-3-phenylprop-2-en-1-ylidene group. It is an inhibitor of aldose reductase (which catalyses the conversion of glucose to sorbitol) and is used for the treatment of some diabetic complications, including neuropathy. It has a role as an EC 1.1.1.21 (aldehyde reductase) inhibitor. It is a member of thiazolidines and a monocarboxylic acid.|Epalrestat is under investigation in clinical trial NCT03244358 (Evaluation of Epalrestat in Metastatic Triple-negative Breast Cancer).|Epalrestat is an orally available, a non-competitive, reversible inhibitor of aldose reductase (AR), with potential antineoplastic, antioxidant, and anti-inflammatory activities. Upon oral administration, epalrestat non-competitively binds to AR, a polyol pathway enzyme that catalyzes reactive oxygen species (ROS)-initiated lipid peroxidation-generated lipid aldehydes and their glutathione conjugates, which have been implicated in the activation of transcription factors such as nuclear factor kappa-light-chain-enhancer of activated B cells (NF-kappa B) and activator protein-1 (AP-1), which control the transcription of many inflammatory cytokines. Increased inflammatory cytokines and growth factors promote cell proliferation, a primary feature in the tumorigenesis process. AR is overexpressed in several oxidative stress- and inflammation-related conditions, including cancer.

Epalrestat Basic Attributes

Molecular Weight：

319.4

Exact Mass：

319.40

EC Number：

1312995-182-4

UNII：

424DV0807X

DSSTox ID：

DTXSID1046479

NCI Thesaurus Code：

C72762

Characteristics

PSA：

115

XLogP3：

3.8

Appearance：

yellow to orange

Density：

1.4±0.1 g/cm3

Melting Point：

210-217 °C

Boiling Point：

516.8°C at 760 mmHg

Flash Point：

266.4±32.9 °C

Refractive Index：

1.706

Water Solubility：

DMSO: soluble5mg/mL, clear (warmed)

Storage Conditions：

-20°C Freezer

Toxicity：

Oral-rat LD50: 5.3 mg/kg; Intravenous-Mouse LD50: 0.255 mg/kg

Flammability characteristics：

Combustible, fires emit nitrogen oxides, sulfur oxides pungently stimulate smoke

Safety Information

Packing level：

Hazard category：

6.1

Transport codes：

2811

wgk germany：

RTECS Number：

XJ5131855

Storage features：

Ventilated, low temperature and dry; stored separately from food materials in warehouse

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H300

GHS Classification：

|Danger|H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

most toxic

Drug Information

MeSH：

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

MeSH Entry Terms：

3-carboxymethyl-5-(methyl-3-phenylpropenylidene)rhodanine

Epalrestat Use and Manufacturing

An aldose reductase inhibitor. It is used in treatment of diabetic neuropathy.

Computed Properties

Molecular Weight:319.4
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:319.03368562
Monoisotopic Mass:319.03368562
Topological Polar Surface Area:115
Heavy Atom Count:21
Complexity:519
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzaldehyde

Chlorine dioxide

Acetic acid

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Epalrestat
Manufacturer	Qinhuangdao Zizhu Pharmaceutical Co., Ltd.

Epalrestat Tablets
Ingredients	Main ingredients of this product: Each tablet of this product contains 50 mg of epalrestat. Chemical name of the main ingredient of this product: 5-[(1Z, 2E)-2-methyl-3-phenylpropylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid.
Indication	Not yet clear.
Specifications	50mg

Epalrestat Capsules
Ingredients	5-[(1Z, 2E)-2-methyl-3-phenylpropenylidene]-4-oxo-2-thioxo-3-thiazolidineacetic acid
Indication	Not yet clear
Specifications	50mg
Manufacturer	YANGTZE River Pharmaceutical Group Nanjing Pharmaceutical. Co., Ltd.

See More Related Drugs

Registered Holders

Zhejiang East-Asia Pharmaceutical Co., Ltd.

China
Active
Kangya of Ningxia Pharmaceutical Co., Ltd.

China
Active
Jiangsu Sinopep-Allsino Biopharmaceutical Co., Ltd.

China
Active

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