Ethacrynic acid
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.
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Chemical Information
| Name | Ethacrynic acid |
|---|---|
| Iupac Chemical Name | 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid |
| Synonyms | Ethacrynic acid; Etacrinic acid; Hydromedin; Crinuryl; Mingit;MK-595; NSC 624008; NSC 85791; Otacril Reomax; Taladren |
| Molecular Formula | C13H12Cl2O4 |
| Molecular Weight | 303.14 |
| Smile | CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl |
| InChiKey | AVOLMBLBETYQHX-UHFFFAOYSA-N |
| 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) |
| CAS Number | 58-54-8 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | 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 |
| Handling | |
| 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. |
| HS Code |
| Targets | |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
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.
Chemical Structure
