Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H11Cl2O4.Na |
Molecular Weight | 325.12 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC([O-])=O)C=C1
InChI
InChIKey=CWCSCNSKBSCYCS-UHFFFAOYSA-M
InChI=1S/C13H12Cl2O4.Na/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);/q;+1/p-1
Molecular Formula | C13H11Cl2O4 |
Molecular Weight | 302.13 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00903Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/16092s042,16093s044lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00903
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/16092s042,16093s044lbl.pdf
Ethacrynic acid is a monosulfonamyl loop or high ceiling diuretic. Ethacrynic acid acts on the ascending limb of the loop of Henle and on the proximal and distal tubules. Urinary output is usually dose dependent and related to the magnitude of fluid accumulation. Water and electrolyte excretion may be increased several times over that observed with thiazide diuretics, since ethacrynic acid inhibits reabsorption of a much greater proportion of filtered sodium than most other diuretic agents. Therefore, ethacrynic acid is effective in many patients who have significant degrees of renal insufficiency. Ethacrynic acid has little or no effect on glomerular filtration or on renal blood flow, except following pronounced reductions in plasma volume when associated with rapid diuresis. Ethacrynic acid 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. Diuretics also lower blood pressure initially by reducing plasma and extracellular fluid volume; cardiac output also decreases, explaining its antihypertensive action. Eventually, cardiac output returns to normal with an accompanying decrease in peripheral resistance. Its mode of action does not involve carbonic anhydrase inhibition. Ethacrynic acid is indicated for the treatment of high blood pressure and edema caused by diseases like congestive heart failure, liver failure, and kidney failure.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Glutathione transferases, rat liver Sources: https://www.ncbi.nlm.nih.gov/pubmed/27457758 |
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Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26950276 |
|||
Target ID: P05023|||Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00903 |
|||
Target ID: CHEMBL1874 Sources: http://www.drugbank.ca/drugs/DB00903 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EDECRIN Approved UseEDECRIN is indicated for treatment of edema when an agent with greater diuretic potential than those
commonly employed is required.
1. Treatment of the edema associated with congestive heart failure, cirrhosis of the liver, and renal disease,
including the nephrotic syndrome.
2. Short-term management of ascites due to malignancy, idiopathic edema, and lymphedema.
3. Short-term management of hospitalized pediatric patients, other than infants, with congenital heart disease
or the nephrotic syndrome.
4. Intravenous SODIUM EDECRIN is indicated when a rapid onset of diuresis is desired, e.g., in acute
pulmonary edema, or when gastrointestinal absorption is impaired or oral medication is not practicable. Launch Date-9.40032E10 |
|||
Primary | EDECRIN Approved UseEDECRIN is indicated for treatment of edema when an agent with greater diuretic potential than those
commonly employed is required.
1. Treatment of the edema associated with congestive heart failure, cirrhosis of the liver, and renal disease,
including the nephrotic syndrome.
2. Short-term management of ascites due to malignancy, idiopathic edema, and lymphedema.
3. Short-term management of hospitalized pediatric patients, other than infants, with congenital heart disease
or the nephrotic syndrome.
4. Intravenous SODIUM EDECRIN is indicated when a rapid onset of diuresis is desired, e.g., in acute
pulmonary edema, or when gastrointestinal absorption is impaired or oral medication is not practicable. Launch Date-9.40032E10 |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg 2 times / day multiple, oral Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: edema Sex: unknown Sources: |
Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (severe) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | severe Disc. AE |
50 mg 2 times / day multiple, oral Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: edema Sex: unknown Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Long-lasting c-fos and NGF mRNA expressions and loss of perikaryal parvalbumin immunoreactivity in the development of epileptogenesis after ethacrynic acid-induced seizure. | 1999 Jul 10 |
|
The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance. | 2000 Aug |
|
Rat liver microsomal lipid peroxidation produced during the oxidative metabolism of ethacrynic acid. | 2001 Apr |
|
Glutathione S-transferases from rainbow trout liver and freshly isolated hepatocytes: purification and characterization. | 2001 Feb |
|
Chloride channel antagonists perturb growth and morphology of Neurospora crassa. | 2001 Jul 24 |
|
Heterologous expression and characterization of alternatively spliced glutathione S-transferases from a single Anopheles gene. | 2001 Jul 26 |
|
Determination and characterization of diuretics in human urine by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry. | 2001 Jun |
|
Purification and characterization of multiple glutathione S-transferase isozymes from Chironomidae larvae. | 2001 Jun |
|
3-Methyleneoxindole: an affinity label of glutathione S-transferase pi which targets tryptophan 38. | 2001 Jun 26 |
|
Determination and multivariate statistical analysis of biochemical responses to environmental contaminants in feral freshwater fish Leuciscus cephalus, L. | 2001 May |
|
Efflux of glutathione conjugate of monochlorobimane from striatal and cortical neurons. | 2001 Oct |
|
Purification and characterization of a glutathione S-transferase from the fungus Cunninghamella elegans. | 2001 Sep 25 |
|
The glutathione system in alkylator resistance. | 2002 |
|
A putative role for S-nitrosoglutathione as the source of nitric oxide in photorelaxation of the mouse gastric fundus. | 2002 Aug 30 |
|
Rapid spectrophotometric method for serum glutathione S-transferases activity. | 2002 Dec |
|
Cellular sensitivity determinants to docetaxel in human gastrointestinal cancers. | 2002 Feb |
|
Purification and characterization of a novel glutathione S-transferase from Asaphis dichotoma. | 2002 Jul 15 |
|
Nipradilol induces vasodilation of canine isolated posterior ciliary artery via stimulation of the guanylyl cyclase-cGMP pathway. | 2002 Jul 26 |
|
Influence of temperature, pH, oxygenation, water-type and substrate on biomarker responses in the freshwater clam Corbicula fluminea (Müller). | 2002 May |
|
Complementary DNA cloning, protein expression, and characterization of alpha-class GSTs from Macaca fascicularis liver. | 2002 Nov |
|
Changes in cell proliferation in rat and guinea pig cochlea after aminoglycoside-induced damage. | 2003 Aug 28 |
|
Ethacrynic acid and the sulfa-sensitive patient. | 2003 Jan 13 |
|
A photosensitive vascular smooth muscle store of nitric oxide in mouse aorta: no dependence on expression of endothelial nitric oxide synthase. | 2003 Mar |
|
Mitochondrial dysfunction and death in motor neurons exposed to the glutathione-depleting agent ethacrynic acid. | 2003 Mar 15 |
|
Characterization of cell death induced by ethacrynic acid in a human colon cancer cell line DLD-1 and suppression by N-acetyl-L-cysteine. | 2003 Oct |
|
The influence of anti-irritants on captopril hydrophilic gel. | 2004 Feb |
|
Effects of pH and the presence of micelles on the resolution of diuretics by reversed-phase liquid chromatography. | 2004 Jan 2 |
|
Time course of efferent fiber and spiral ganglion cell degeneration following complete hair cell loss in the chinchilla. | 2004 Jan 30 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Can also be used iv:
The usual intravenous dose for the average sized adult is 50 mg, or 0.5 to 1.0 mg per kg of body weight. Usually only one dose has been necessary; occasionally a second dose at a new injection site, to avoid possible
thrombophlebitis, may be required. A single intravenous dose not exceeding 100 mg has been used in critical situations
Dosage: To Initiate Diuresis
In Adults: The smallest dose required to produce gradual weight loss (about 1 to 2 pounds per day) is
recommended. Onset of diuresis usually occurs at 50 to 100 mg for adults. After diuresis has been achieved, the minimally effective dose (usually from 50 to 200 mg daily) may be given on a continuous or intermittent dosage schedule.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26950276
Ethacrynic acid (10uM) induced both apoptosis and necroptosis in primary CLL cells.
Substance Class |
Chemical
Created
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admin
on
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Wed Jul 05 23:16:35 UTC 2023
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Record UNII |
K41MYV7MPM
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Record Status |
Validated (UNII)
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C49184
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ACTIVE MOIETY |