Ethacrynic acid

• CAT Number: R048634
• CAS Number: 58-54-8
• Molecular Formula: C13H12Cl2O4
• Molecular Weight: 303.14
• Purity: ≥95%
• Synonyms: 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
• InChI: 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)
• InChIKey: AVOLMBLBETYQHX-UHFFFAOYSA-N
• SMILES: CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl

Ethacrynic acid has anti-inflammatory and anticancer activity. Ethacrynic acid is an orally active diuretic. Ethacrynic acid is an inhibitor of glutathione S-transferase (GSTs) and Wnt signaling pathways. Ethacrynic acid is a radiosensitizer. Ethacrynic acid can inhibit airway smooth muscle (ASM) contraction in mice. Ethacrynic acid can increase the outflow of aqueous humor from the eye for the study of glaucoma[1][2][3][4][5][6][7][8][9].
Ethacrynic acid (50 μM; 24 h) inhibits Wnt/β-catenin signaling in CLL cells[1].
Ethacrynic acid (1-100 μM; 48 h) is cytotoxic in CLL cells with an IC50 of 8.56 μM[1].
Ethacrynic acid (0.01-0.25 mmol/L; 30 min) increases aqueous humor outflow facility acutely in eye and the outflow rate increases from 28% to 105%[2].
Ethacrynic acid (10-100 μM; 30 min) can inhibit the activation of NF-κB pathway in RAW264.7 cells induced by LPS (100 ng/mL) and has anti-inflammatory activity[3].
Ethacrynic acid (20 μM/mL; 2 h) can increase the radiation intensity in MCF-7 cancer cells after radiation exposure[3].
Ethacrynic acid (100 μmol/L; 62.5-250 min) inhibits tracheal ring contraction induced by high -K+ (80 mmol/L) and acetylcholine (ACh, 100 µmol/L) in a dose-dependent manner with EC50 of 40.28 µmol/L and 56.22 µmol/L, respectively[8].
Ethacrynic acid (100 μmol/L; 500-2500 s) decreases the intracellular Ca2+ concentration induced by high -K+ and ACh from 0.40 to 0.16, 0.50 to 0.39, respectively[8].
Ethacrynic acid (450 μg/mouse; Oral gavage; Once daily for 60 days) can inhibit tumor growth in the mice[5].

Reference

[1]. Lu D, et al. Ethacrynic acid exhibits selective toxicity to chronic lymphocytic leukemia cells by inhibition of the Wnt/beta-catenin pathway. PLoS One. 2009 Dec 14;4(12):e8294.
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[2]. Liang LL, et al. Ethacrynic acid increases facility of outflow in the human eye in vitro. Arch Ophthalmol. 1992 Jan;110(1):106-9.
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[3]. Han Y,et al. Ethacrynic acid inhibits multiple steps in the NF-kappaB signaling pathway. Shock. 2005 Jan;23(1):45-53.
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[4]. Khil MS, et al. Ethacrynic acid: a novel radiation enhancer in human carcinoma cells. Int J Radiat Oncol Biol Phys. 1996 Jan 15;34(2):375-80.
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[5]. Kim Y, et al. In vivo efficacy of the diuretic agent ethacrynic acid against multiple myeloma. Leuk Res. 2012 May;36(5):598-600.
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[6]. Li XQ, et al. Metabolism of Strained Rings: Glutathione S-transferase-Catalyzed Formation of a Glutathione-Conjugated Spiro-azetidine without Prior Bioactivation. Drug Metab Dispos. 2019 Nov;47(11):1247-1256.
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[7]. Harada T, et al. Ethacrynic acid decreases expression of proinflammatory intestinal wall cytokines and ameliorates gastrointestinal stasis in murine postoperative ileus. Clinics (Sao Paulo). 2018 Oct 18;73:e332.
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[8]. Zhao XX, et al. [Ethacrynic acid inhibits airway smooth muscle contraction in mice]. Sheng Li Xue Bao. 2019 Dec 25;71(6):863-873. Chinese. PMID: 31879742.
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[9]. Byun HJ, Kang KJ, Park MK, Lee HJ, Kang JH, Lee EJ, Kim YR, Kim HJ, Kim YW, Jung KC, Kim SY, Lee CH. Ethacrynic Acid Inhibits Sphingosylphosphorylcholine-Induced Keratin 8 Phosphorylation and Reorganization via Transglutaminase-2 Inhibition. Biomol Ther (Seoul). 2013 Sep 30;21(5):338-42.
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[10].