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 | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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 |
|||
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 Date1967 |
|||
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 Date1967 |
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 |
---|---|---|
Ethacrynic acid-induced convulsions and brain neurotransmitters in mice. | 1992 Oct 6 |
|
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 |
|
Amine oxidase, spermine, and hyperthermia induce cytotoxicity in P-glycoprotein overexpressing multidrug resistant Chinese hamster ovary cells. | 2001 |
|
Rat liver microsomal lipid peroxidation produced during the oxidative metabolism of ethacrynic acid. | 2001 Apr |
|
Overexpression of glutathione-S-transferase A1 in benign adrenocortical adenomas from patients with Cushing's syndrome. | 2001 Apr |
|
Cyclo-oxygenase and lipoxygenase pathways in mast cell dependent-neurogenic inflammation induced by electrical stimulation of the rat saphenous nerve. | 2001 Apr |
|
Overexpression of glutathione S-transferase II and multidrug resistance transport proteins is associated with acquired tolerance to inorganic arsenic. | 2001 Aug |
|
DCPIB is a novel selective blocker of I(Cl,swell) and prevents swelling-induced shortening of guinea-pig atrial action potential duration. | 2001 Dec |
|
Quantitative imaging of glutathione in hippocampal neurons and glia in culture using monochlorobimane. | 2001 Dec 1 |
|
Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta. | 2001 Jan 30 |
|
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 |
|
Ethacrynic acid inhibits pancreatic exocrine secretion. | 2001 Nov |
|
Decreased glutathione S-transferase expression and activity and altered sex steroids in Lake Apopka brown bullheads (Ameiurus nebulosus). | 2001 Nov 12 |
|
Toxicity of ethacrynic acid in isolated rat hepatocytes. | 2002 Apr |
|
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 |
|
Influence of antioxidant depletion on nitrergic relaxation in the pig gastric fundus. | 2002 Feb |
|
Cellular sensitivity determinants to docetaxel in human gastrointestinal cancers. | 2002 Feb |
|
Glutathione might exert an important function in caerulein-stimulated amylase release in isolated rat pancreatic acini. | 2002 Jan |
|
Differential effects of garlic oil and its three major organosulfur components on the hepatic detoxification system in rats. | 2002 Jan 16 |
|
Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells. | 2002 Jul 12 |
|
Purification and characterization of a novel glutathione S-transferase from Asaphis dichotoma. | 2002 Jul 15 |
|
The organochlorine pesticide residues and antioxidant enzyme activities in human breast tumors: is there any association? | 2002 Mar |
|
[The role of thiol oxidants in inhibition of pancreatic exocrine secretory function and glutathione]. | 2002 May |
|
Intra-cochlear administration of dexamethasone attenuates aminoglycoside ototoxicity in the guinea pig. | 2002 May |
|
Glutathione S-transferase of the malarial parasite Plasmodium falciparum: characterization of a potential drug target. | 2002 May |
|
Combined effects of cadmium and nickel on testicular xenobiotic metabolizing enzymes in rats. | 2002 Nov |
|
Complementary DNA cloning, protein expression, and characterization of alpha-class GSTs from Macaca fascicularis liver. | 2002 Nov |
|
Ethacrynic acid rapidly and selectively abolishes blood flow in vessels supplying the lateral wall of the cochlea. | 2002 Nov |
|
Interaction between metamizol and tramadol in a model of acute visceral pain in rats. | 2003 |
|
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 |
|
Exploration of in vitro pro-drug activation and futile cycling by glutathione S-transferases: thiol ester hydrolysis and inhibitor maturation. | 2003 Jun 15 |
|
Modulation of pumpkin glutathione S-transferases by aldehydes and related compounds. | 2003 May |
|
Neurotrophic factor effects on oxidative stress-induced neuronal death. | 2003 May |
|
Analysis of energy metabolism and mechanism of loop diuretics in the thick ascending limb of Henle's loop in dog kidneys. | 2003 May |
|
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 |
|
Continuous administration of antisense oligonucleotides to c-fos reduced the development of seizure susceptibility after ethacrynic acid-induced seizure in mice. | 2003 Sep 25 |
|
Characterization and molecular cloning of a glutathione S-transferase from the whitefly Bemisia tabaci (Hemiptera: Aleyrodidae). | 2004 Apr |
|
Glutathione S-transferases and esterases in placenta after normal and pre-eclamptic pregnancies. | 2004 Apr |
|
Inhibition of glucose-induced electrical activity in rat pancreatic beta-cells by DCPIB, a selective inhibitor of volume-sensitive anion currents. | 2004 Apr 5 |
|
Controlled release of ethacrynic acid from poly(lactide-co-glycolide) films for glaucoma treatment. | 2004 Aug |
|
The influence of anti-irritants on captopril hydrophilic gel. | 2004 Feb |
|
Risk of hospitalization for upper gastrointestinal tract bleeding. | 2004 Jan |
|
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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Record UNII |
K41MYV7MPM
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Record Status |
Validated (UNII)
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Record Version |
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C49184
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