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SML1083

Ethacrynic acid

Name: Ethacrynic acid
Brand: SIGMA

≥97% (HPLC), glutathione S-transferase inhibitor, powder

Synonym(s):

2-[2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid, ECA, Etacrynic acid, [2,3-Dichloro-4-(2-ethylacryloyl)phenoxy]acetic acid, (2,3-Dichloro-4-[2-methylenebutyryl]phenoxy)acetic acid

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About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₂Cl₂O₄

CAS Number:

58-54-8

Molecular Weight:

303.14

NACRES:

NA.77

PubChem Substance ID:

329825461

UNSPSC Code:

12352106

EC Number:

200-384-1

MDL number:

MFCD00056693

Assay:

≥97% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Ethacrynic acid, ≥97% (HPLC)

Quality Level

100

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

ClC1=C(Cl)C(C(C(CC)=C)=O)=CC=C1OCC(O)=O

InChI

1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)

InChI key

AVOLMBLBETYQHX-UHFFFAOYSA-N

Gene Information

human ... SLC12A1(6557)

Description

Biochem/physiol Actions

Ethacrynic acid increases the cytotoxicity of chlorambucil in rat and human tumor cell lines.

Ethacrynic acid is non sulfonamide loop diuretic that is used to treat high blood pressure and the swelling caused by diseases like congestive heart failure. Ethacrynic acid blocks sodium-potassium-chloride cotransport. Also, Ethacrynic acid potently inhibits glutathione S-transferase family members. Studies show that ethacrynic acid potently inhibits Tgase-2 (transglutaminase-2) dependent metastasis of cancer cells including lung and pancreatic cancers.

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pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Effect of a glutathione S-transferase inhibitor on oxidative stress and ischemia-reperfusion-induced apoptotic signalling of cultured cardiomyocytes.

E Röth et al.

Experimental and clinical cardiology, 16(3), 92-96 (2011-11-09)

Oxidative stress and ischemia-reperfusion (I/R) injury are crucial in the pathogenesis of cardiovascular diseases. The antioxidant glutathione S-transferase (GST) is responsible for the high-capacity metabolic inactivation of electrophilic compounds and toxic substrates. The main objective of the present study was

Inhibition of rat and human glutathione S-transferase isoenzymes by ethacrynic acid and its glutathione conjugate.

Ploemen J H, et al.

Biochemical Pharmacology, 40(7), 1631-1635 (1990)

Glutathione-S-transferase activity in various organs of Crocodylus siamensis and its attenuation role in aflatoxin B1-induced cell apoptosis in human hepatocarcinoma cells.

Piriyaporn Thiendedsakul et al.

Veterinary world, 15(1), 46-54 (2022-04-05)

The crocodile is a model for studying relevant sources of environmental contamination. They were determined an appropriate biomonitoring species for various toxins. The cytosolic and microsomal fraction of crocodiles plays a role in detoxifying xenobiotics. Cytochrome P450 1A2 (CYP1A2) metabolizes

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Global Trade Item Number

SKU	GTIN
SML1083-10MG	04061837107566