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SML1083

Sigma-Aldrich

Ethacrynic acid

≥97% (HPLC)

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
EC Number:
200-384-1
MDL number:
MFCD00056693
UNSPSC Code:
12352106
PubChem Substance ID:
329825461
NACRES:
NA.77

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)

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Hyun Jung Byun et al.
Biomolecules & therapeutics, 21(5), 338-342 (2013-11-19)
Sphingosylphosphorylcholine (SPC) is significantly increased in the malicious ascites of tumor patients and induces perinuclear reorganization of keratin 8 (K8) filaments in PANC-1 cells. The reorganization contributes to the viscoelasticity of metastatic cancer cells resulting in increased migration. Recently, we
Raymond P Wu et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(16), 7479-7484 (2010-04-07)
Recent studies show that redox-active small molecules are selectively cytotoxic to chronic lymphocytic leukemia (CLL). Although elevated levels of reactive oxygen species in CLL cells have been implicated, the molecular mechanism underlying this selectivity is unclear. In other cell types
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