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MedKoo Cat#: 317791 | Name: Ethacrynic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Etharcrynic Acid is a compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic. Ethacrynic Acid is an unsaturated ketone derivative of aryloxyacetic acid without a sulfonamide substituent belonging to the class of loop diuretics. Ethacrynic acid is extensively bound to plasma proteins; both ethacrynic acid in its unchanged form as well as its metabolites are excreted in bile and urine.

Chemical Structure

Ethacrynic acid
Ethacrynic acid
CAS#58-54-8 (free acid)

Theoretical Analysis

MedKoo Cat#: 317791

Name: Ethacrynic acid

CAS#: 58-54-8 (free acid)

Chemical Formula: C13H12Cl2O4

Exact Mass: 302.0113

Molecular Weight: 303.14

Elemental Analysis: C, 51.51; H, 3.99; Cl, 23.39; O, 21.11

Price and Availability

Size Price Availability Quantity
500mg USD 90.00 Ready to ship
1g USD 150.00 Ready to ship
2g USD 250.00 Ready to ship
5g USD 450.00 Ready to ship
10g USD 750.00 Ready to ship
20g USD 1,250.00 Ready to ship
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Related CAS #
6500-81-8 (sodium) 58-54-8 (free acid)
Synonym
Ethacrynic acid; Etacrinic acid; Hydromedin; Crinuryl; Mingit;MK-595; NSC 624008; NSC 85791; Otacril Reomax; Taladren
IUPAC/Chemical Name
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
InChi Key
AVOLMBLBETYQHX-UHFFFAOYSA-N
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)
SMILES Code
CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Ethacrynic acid is an inhibitor of glutathione S-transferases (GSTs) and a potent inhibitor of NF-kB-signaling pathway.
In vitro activity:
The effects of ethacrynic acid (ECA) were examined on sphingosylphosphorylcholine (SPC) or TGF-β1-induced EMT process in A549 and H1299 cells via reverse transcription polymerase chain reaction and Western blotting. It was found that ECA inhibited SPC-induced EMT and SPC-induced WNT signalling in EMT. It was observed that SPC induces the expression of NDP [Norrie disease protein] and WNT-2, whereas ECA suppressed their expression. SPC-induced WNT activation, EMT, migration, and invasion were suppressed by NDP small-interfering RNA (siNDP), but NDP overexpression (pNDP) enhanced these events in A549 and H1299 cells. Accordingly, NDP expression may influence lung cancer prognosis. In summary, these results revealed that ECA inhibited SPC or TGF-β1-induced EMT in A549 and H1299 lung cancer cells by downregulating NDP expression and inhibiting WNT activation. Therefore, ECA might be a new drug candidate for lung cancer treatment. Reference: Biochem Pharmacol. 2021 Jan;183:114339. https://linkinghub.elsevier.com/retrieve/pii/S0006-2952(20)30575-X
In vivo activity:
The aim of this study was to investigate the inhibitory effect and the underlying mechanism of ethacrynic acid (EA) on the contraction in mice. BL-420S force measuring system was used to measure the tension of mouse tracheal rings. The whole cell patch clamp technique was utilized to record the channel currents of airway smooth muscle (ASM) cells. The calcium imaging system was used to determine the intracellular Ca2+ concentration ([Ca2+]i) in ASM cells. The results showed that EA significantly inhibited the high K+ (80 mmol/L) and acetylcholine (ACh, 100 µmol/L)-induced contraction of mouse tracheal rings in a dose-dependent manner. The maximal relaxation percentages were (97.02 ± 1.56)% and (85.21 ± 0.03)%, and the median effective concentrations were (40.28 ± 2.20) μmol/L and (56.22 ± 7.62) μmol/L, respectively. EA decreased the K+ and ACh-induced elevation of [Ca2+]i from 0.40 ± 0.04 to 0.16 ± 0.01 and from 0.50 ± 0.01 to 0.39 ± 0.01, respectively. In addition, EA inhibited L-type voltage-dependent calcium channel (LVDCC) and store-operated calcium channel (SOCC) currents in ASM cells, and Ca2+ influx. Moreover, EA decreased the resistance of the respiratory system (Rrs) in vivo in mice. These results indicated that EA inhibits LVDCC and SOCC, which results in termination of Ca2+ influx and decreases of [Ca2+]i, leading to relaxation of ASM. Taken together, EA might be a potential bronchodilator. Reference: Sheng Li Xue Bao. 2019 Dec 25;71(6):863-873. http://www.actaps.com.cn/qikan/manage/wenzhang/2019-6-07.pdf
Solvent mg/mL mM
Solubility
DMSO 61.0 202.22
Water 27.5 90.72
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 303.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Yu L, Kim HJ, Park MK, Byun HJ, Kim EJ, Kim B, Nguyen MT, Kim JH, Kang GJ, Lee H, Kim SY, Rho SB, Lee CH. Ethacrynic acid, a loop diuretic, suppresses epithelial-mesenchymal transition of A549 lung cancer cells via blocking of NDP-induced WNT signaling. Biochem Pharmacol. 2021 Jan;183:114339. doi: 10.1016/j.bcp.2020.114339. Epub 2020 Nov 13. PMID: 33189676.
In vivo protocol:
1. Zhao XX, Chen WW, Chen YY, Liu MS, Li MY, Cao L, Liu QH. [Ethacrynic acid inhibits airway smooth muscle contraction in mice]. Sheng Li Xue Bao. 2019 Dec 25;71(6):863-873. Chinese. PMID: 31879742.
1: Nguyen BD, Roarke MC, Young JR, Yang M, Osborn HH. Diuretic Renal Scintigraphy in Patients with Sulfonamide Allergies: Possible Alternative Use of Ethacrynic Acid. J Nucl Med Technol. 2015 Dec;43(4):239-41. doi: 10.2967/jnmt.115.161331. Epub 2015 Oct 15. PubMed PMID: 26471332. 2: Jang JH, Lee HS, Oh SH, Park MH. Efficacy of the cat deafening method: Co-administration of ethacrynic acid and kanamycin. Acta Otolaryngol. 2015 Nov 25:1-4. [Epub ahead of print] PubMed PMID: 26605909. 3: Dou W, Wu JJ, Chen SC, Wei DD, Wang JJ. Effects of Ethacrynic Acid Addition to Diet on Fitness and Development in the Psocid Liposcelis bostrychophila Badonnel. Environ Entomol. 2015 Oct 16. pii: nvv157. [Epub ahead of print] PubMed PMID: 26475825. 4: Ward WM, Hoffman JD, Loo G. Genotoxic effect of ethacrynic acid and impact of antioxidants. Toxicol Appl Pharmacol. 2015 Jul 1;286(1):17-26. doi: 10.1016/j.taap.2015.03.016. Epub 2015 Mar 25. PubMed PMID: 25817893. 5: Agonigi G, Riedel T, Zacchini S, Păunescu E, Pampaloni G, Bartalucci N, Dyson PJ, Marchetti F. Synthesis and Antiproliferative Activity of New Ruthenium Complexes with Ethacrynic-Acid-Modified Pyridine and Triphenylphosphine Ligands. Inorg Chem. 2015 Jul 6;54(13):6504-12. doi: 10.1021/acs.inorgchem.5b00802. Epub 2015 Jun 15. PubMed PMID: 26073654. 6: El Brahmi N, Mignani SM, Caron J, El Kazzouli S, Bousmina MM, Caminade AM, Cresteil T, Majoral JP. Investigations on dendrimer space reveal solid and liquid tumor growth-inhibition by original phosphorus-based dendrimers and the corresponding monomers and dendrons with ethacrynic acid motifs. Nanoscale. 2015 Mar 7;7(9):3915-22. doi: 10.1039/c4nr05983b. PubMed PMID: 25503793. 7: Ricci Z, Haiberger R, Pezzella C, Garisto C, Favia I, Cogo P. Furosemide versus ethacrynic acid in pediatric patients undergoing cardiac surgery: a randomized controlled trial. Crit Care. 2015 Jan 7;19:2. doi: 10.1186/s13054-014-0724-5. PubMed PMID: 25563826; PubMed Central PMCID: PMC4305226. 8: Wang M, Gorasiya S, Antoine DJ, Sitapara RA, Wu W, Sharma L, Yang H, Ashby CR Jr, Vasudevan D, Zur M, Thomas DD, Mantell LL. The compromise of macrophage functions by hyperoxia is attenuated by ethacrynic acid via inhibition of NF-κB-mediated release of high-mobility group box-1. Am J Respir Cell Mol Biol. 2015 Feb;52(2):171-82. doi: 10.1165/rcmb.2013-0544OC. PubMed PMID: 24992505; PubMed Central PMCID: PMC4370245. 9: Nagy T, Kovács V, Hardi P, Veres TG, Takács I, Jancsó G, Sinay L, Fazekas G, Pintér Ö, Arató E. Inhibition of Glutathione S-Transferase by Ethacrynic Acid Augments Ischemia-Reperfusion Damage and Apoptosis and Attenuates the Positive Effect of Ischemic Postconditioning in a Bilateral Acute Hindlimb Ischemia Rat Model. J Vasc Res. 2015;52(1):53-61. doi: 10.1159/000381984. Epub 2015 May 29. PubMed PMID: 26045187. 10: Miller JL, Schaefer J, Tam M, Harrison DL, Johnson PN. Ethacrynic Acid continuous infusions in critically ill pediatric patients. J Pediatr Pharmacol Ther. 2014 Jan;19(1):49-55. doi: 10.5863/1551-6776-19.1.49. PubMed PMID: 24782692; PubMed Central PMCID: PMC3998969. 11: 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. doi: 10.4062/biomolther.2013.066. PubMed PMID: 24244820; PubMed Central PMCID: PMC3825196. 12: Liu G, Wang R, Wang Y, Li P, Zhao G, Zhao L, Jing Y. Ethacrynic acid oxadiazole analogs induce apoptosis in malignant hematologic cells through downregulation of Mcl-1 and c-FLIP, which was attenuated by GSTP1-1. Mol Cancer Ther. 2013 Sep;12(9):1837-47. doi: 10.1158/1535-7163.MCT-12-1224. Epub 2013 Jun 26. PubMed PMID: 23804706. 13: Na YR, Han KC, Park H, Yang EG. Menadione and ethacrynic acid inhibit the hypoxia-inducible factor (HIF) pathway by disrupting HIF-1α interaction with p300. Biochem Biophys Res Commun. 2013 May 17;434(4):879-84. doi: 10.1016/j.bbrc.2013.04.044. Epub 2013 Apr 22. PubMed PMID: 23618863. 14: Zhang P, Chen JH, Dong X, Tang MT, Gao LY, Zhao GS, Yu LG, Guo XL. 6r, a novel oxadiazole analogue of ethacrynic acid, exhibits antitumor activity both in vitro and in vivo by induction of cell apoptosis and S-phase arrest. Biomed Pharmacother. 2013 Feb;67(1):58-65. doi: 10.1016/j.biopha.2012.10.011. Epub 2012 Nov 19. PubMed PMID: 23201007. 15: Wang R, Liu C, Xia L, Zhao G, Gabrilove J, Waxman S, Jing Y. Ethacrynic acid and a derivative enhance apoptosis in arsenic trioxide-treated myeloid leukemia and lymphoma cells: the role of glutathione S-transferase p1-1. Clin Cancer Res. 2012 Dec 15;18(24):6690-701. doi: 10.1158/1078-0432.CCR-12-0770. Epub 2012 Oct 18. PubMed PMID: 23082001; PubMed Central PMCID: PMC3525753. 16: Kim Y, Gast SM, Endo T, Lu D, Carson D, Schmidt-Wolf IG. In vivo efficacy of the diuretic agent ethacrynic acid against multiple myeloma. Leuk Res. 2012 May;36(5):598-600. doi: 10.1016/j.leukres.2012.01.025. Epub 2012 Mar 2. PubMed PMID: 22386728. 17: Li T, Liu G, Li H, Yang X, Jing Y, Zhao G. The synthesis of ethacrynic acid thiazole derivatives as glutathione S-transferase pi inhibitors. Bioorg Med Chem. 2012 Apr 1;20(7):2316-22. doi: 10.1016/j.bmc.2012.02.011. Epub 2012 Feb 13. PubMed PMID: 22370342. 18: Zanellato I, Bonarrigo I, Sardi M, Alessio M, Gabano E, Ravera M, Osella D. Evaluation of platinum-ethacrynic acid conjugates in the treatment of mesothelioma. ChemMedChem. 2011 Dec 9;6(12):2287-93. doi: 10.1002/cmdc.201100426. Epub 2011 Oct 24. PubMed PMID: 22025407. 19: Liu H, Ding DL, Jiang HY, Wu XW, Salvi R, Sun H. Ototoxic destruction by co-administration of kanamycin and ethacrynic acid in rats. J Zhejiang Univ Sci B. 2011 Oct;12(10):853-61. doi: 10.1631/jzus.B1100040. PubMed PMID: 21960349; PubMed Central PMCID: PMC3190101. 20: Schmidt M, Kim Y, Gast SM, Endo T, Lu D, Carson D, Schmidt-Wolf IG. Increased in vivo efficacy of lenalidomide and thalidomide by addition of ethacrynic acid. In Vivo. 2011 May-Jun;25(3):325-33. PubMed PMID: 21576405.