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Ethacrynic acid (also known as MK-595, NSC-624008, NSC-85791, Hydromedin, Crinuryl, Mingit, Etacrinic acid, Otacril Reomax, Taladren, and Edecrin) is a high ceiling loop diuretic that inhibits the Na+/K+/2Cl-cotransporter NKCC2. The swelling brought on by conditions like congestive heart failure, liver failure, and kidney failure is treated with it, as well as edema, high blood pressure, and these conditions. It works as a high ceiling loop diuretic and has anticancer properties as well as cytotoxicity against primary chronic lymphocytic leukemia cells.
| Targets |
L-type calcium channel
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|---|---|
| ln Vitro |
In CLL cells, ephacrynic acid (50 μM; 24 hours) suppresses Wnt/β-catenin signaling [1]. With an IC50 of 8.56 μM, ethanolic acid (1-100 μM; 48 hours) is cytotoxic to CLL cells [1]. The eye's aqueous humor rises in response to diuretic acid (0.01-0.25 mmol/L; 30 minutes), and the rate of water outflow increases from 28% to 105% [2]. Diuric acid has anti-inflammatory properties and can decrease the activation of NF-κB staining in RAW264.7 cells when used in LPS (100 ng/mL) at 10-100 μM for 30 minutes [3]. MCF-7 spots exposed to radiation are improved by ethanolacrynic acid (20 μM/mL; 2 hours). High-K+ (80 mmol/L) and acetylcholine (acetylcholine, ACh, 100 μmol/L) are inhibited by ethanolic acid (100 μmol/L; 62.5-250 minutes). In mice, the EC50 resulting from contraction of the tracheal ring was 40.28 µmol/L and 56.22 µmol/L, respectively[8]. The intracellular Ca2+ concentrations caused by high K+ and ACh were decreased from 0.40 to 0.16 and from 0.50 to 0.39, respectively, by ethacrynic acid (100 µmol/L; 500-2500 seconds) [8]. Real-time polymerase chain reaction
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| ln Vivo |
Ethacrynic Acid (450 μg/mouse; oral form; once daily for 60 days) suppresses tumor growth in mice [5].
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| Cell Assay |
RT-PCR[1]
Cell Types: Chronic lymphocytic leukemia (CLL) Tested Concentrations: 1 μM, 10 μM, 100 μM Incubation Duration: 16 h Experimental Results: Inhibition of the expression of LEF-1, Cyclin D1 and Fibronectin was concentration-dependent. (LEF-1, Cyclin D1, and Fibronectin are established target genes of the Wnt/b-catenin pathway). Western Blot Analysis [3] Cell Types: RAW 264.7 Tested Concentrations: 10 μM, 20 μM, 50 μM, 100 μM; before LPS treatment (100 ng/mL; 1 h) Incubation Duration: 30 min Experimental Results: Inhibition of iNOS mRNA expression. Inhibits the degradation of IκBα and IκBβ. |
| Animal Protocol |
Animal/Disease Models: Myeloma Balb/c mouse model [5]
Doses: 450 μg/mouse: po (oral gavage); one time/day for 60 days. balb/c (Bagg ALBino) mouse were injected subcutaneously (sc) (sc) with 5 × 105 MPC11 myeloma cells. Experimental Results: Dramatically inhibited tumor growth. |
| References |
[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.
[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. [3]. Han Y,et al. Ethacrynic acid inhibits multiple steps in the NF-kappaB signaling pathway. Shock. 2005 Jan;23(1):45-53. [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. [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. [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. [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. [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. [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. [10]. |
| Molecular Formula |
C13H12CL2O4
|
|---|---|
| Molecular Weight |
303.14
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| Exact Mass |
302.01126
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| Elemental Analysis |
C, 51.51; H, 3.99; Cl, 23.39; O, 21.11
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| CAS # |
58-54-8
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| Related CAS # |
Ethacrynic acid sodium;6500-81-8
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| Appearance |
Solid powder
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| SMILES |
CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl
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| InChi Key |
AVOLMBLBETYQHX-UHFFFAOYSA-N
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| InChi Code |
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)
|
| Chemical Name |
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
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| Synonyms |
Taladren; Ethacrynic acid; Etacrinic acid; Hydromedin; Otacril Reomax; Crinuryl; MK-595; Mingit; NSC 624008; NSC 85791
|
| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 61~100 mg/mL (201.2~329.9 mM)
H2O: ~27.5 mg/mL (~90.7 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.25 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.25 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 1 mg/mL (3.30 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2988 mL | 16.4940 mL | 32.9881 mL | |
| 5 mM | 0.6598 mL | 3.2988 mL | 6.5976 mL | |
| 10 mM | 0.3299 mL | 1.6494 mL | 3.2988 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02852564 | Completed | Drug: Ethacrynic Acid | Bladder Cancer | Eugene Lee, MD | August 2016 | Phase 1 |
| NCT01628731 | Completed | Drug: furosemide Drug: ethacrynic acid |
Fluid Overload | Bambino Gesù Hospital and Research Institute |
October 2012 | Phase 3 |
| NCT02051946 | Completed | Device: Retroject Device Drug: balanced salt solution |
Glaucoma | Molly Walsh | May 2014 | Phase 1 Phase 2 |
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