Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H12Cl2O4 |
Molecular Weight | 303.138 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1
InChI
InChIKey=AVOLMBLBETYQHX-UHFFFAOYSA-N
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)
Molecular Formula | C13H12Cl2O4 |
Molecular Weight | 303.138 |
Charge | 0 |
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 |
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Target ID: P05023|||Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00903 |
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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 |
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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 |
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Ethacrynic acid-induced convulsions and brain neurotransmitters in mice. | 1992 Oct 6 |
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Induction of glutathione S-transferase activity and protein expression in brown bullhead (Ameiurus nebulosus) liver by ethoxyquin. | 2001 Jul |
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Detection of drug-induced apoptosis and necrosis in human cervical carcinoma cells using 1H NMR spectroscopy. | 2001 Mar |
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Efflux of glutathione conjugate of monochlorobimane from striatal and cortical neurons. | 2001 Oct |
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Purification and characterization of a glutathione S-transferase from the fungus Cunninghamella elegans. | 2001 Sep 25 |
|
Solutol and cremophor products as new additives in suppository formulation. | 2002 |
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Chinchilla models of selective cochlear hair cell loss. | 2002 Dec |
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Rapid spectrophotometric method for serum glutathione S-transferases activity. | 2002 Dec |
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Influence of antioxidant depletion on nitrergic relaxation in the pig gastric fundus. | 2002 Feb |
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Peptidomimetic glutathione analogues as novel gammaGT stable GST inhibitors. | 2002 Jan |
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Purification and characterization of a novel glutathione S-transferase from Asaphis dichotoma. | 2002 Jul 15 |
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[The role of thiol oxidants in inhibition of pancreatic exocrine secretory function and glutathione]. | 2002 May |
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Complementary DNA cloning, protein expression, and characterization of alpha-class GSTs from Macaca fascicularis liver. | 2002 Nov |
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Ethacrynic acid rapidly and selectively abolishes blood flow in vessels supplying the lateral wall of the cochlea. | 2002 Nov |
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Induction of cytosolic glutathione S-transferases from Atlantic eel (Anguilla Anguilla) after intraperitoneal treatment with polychlorinated biphenyls. | 2002 Oct 7 |
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Substrate specificity of mouse aldo-keto reductase AKR7A5. | 2003 Feb 1 |
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A photosensitive vascular smooth muscle store of nitric oxide in mouse aorta: no dependence on expression of endothelial nitric oxide synthase. | 2003 Mar |
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Mitochondrial dysfunction and death in motor neurons exposed to the glutathione-depleting agent ethacrynic acid. | 2003 Mar 15 |
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Characterization of an ectonucleoside triphosphate diphosphohydrolase 1 activity in alkaline phosphatase-depleted rat osseous plate membranes: possible functional involvement in the calcification process. | 2003 Mar 21 |
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Modulation of pumpkin glutathione S-transferases by aldehydes and related compounds. | 2003 May |
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Neurotrophic factor effects on oxidative stress-induced neuronal death. | 2003 May |
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Late dosing with ethacrynic acid can reduce gentamicin concentration in perilymph and protect cochlear hair cells. | 2003 Nov |
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Improved neural representation of vowels in electric stimulation using desynchronizing pulse trains. | 2003 Oct |
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The influence of anti-irritants on captopril hydrophilic gel. | 2004 Feb |
|
Transport of 99mTc-MAG3 via rat renal organic anion transporter 1. | 2004 Jan |
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Effects of pH and the presence of micelles on the resolution of diuretics by reversed-phase liquid chromatography. | 2004 Jan 2 |
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
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M5DP350VZV
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NCI_THESAURUS |
C49184
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QC03CC01
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C03CC01
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380
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N0000175590
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N0000175366
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DB00903
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ETACRYNIC ACID
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m5042
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DTXSID3025257
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Ethacrynic Acid
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Related Record | Type | Details | ||
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DEGRADENT -> PARENT |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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DEGRADENT -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
POTENCY
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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