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 Date-9.40032E10 |
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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 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 |
---|---|---|
Ethacrynic acid-induced convulsions and brain neurotransmitters in mice. | 1992 Oct 6 |
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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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Decreased glutathione S-transferase expression and activity and altered sex steroids in Lake Apopka brown bullheads (Ameiurus nebulosus). | 2001 Nov 12 |
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Purification and characterization of a glutathione S-transferase from the fungus Cunninghamella elegans. | 2001 Sep 25 |
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A putative role for S-nitrosoglutathione as the source of nitric oxide in photorelaxation of the mouse gastric fundus. | 2002 Aug 30 |
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Glutathione might exert an important function in caerulein-stimulated amylase release in isolated rat pancreatic acini. | 2002 Jan |
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Peptidomimetic glutathione analogues as novel gammaGT stable GST inhibitors. | 2002 Jan |
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Intra-cochlear administration of dexamethasone attenuates aminoglycoside ototoxicity in the guinea pig. | 2002 May |
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Cloning and expression of a novel Mu class murine glutathione transferase isoenzyme. | 2002 Sep 15 |
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Characterization of the electrophile binding site and substrate binding mode of the 26-kDa glutathione S-transferase from Schistosoma japonicum. | 2003 Apr 1 |
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Dopamine-induced oxidative stress in neurons with glutathione deficit: implication for schizophrenia. | 2003 Aug 1 |
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Changes in cell proliferation in rat and guinea pig cochlea after aminoglycoside-induced damage. | 2003 Aug 28 |
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Ethacrynic acid and the sulfa-sensitive patient. | 2003 Jan 13 |
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Engineering a new C-terminal tail in the H-site of human glutathione transferase P1-1: structural and functional consequences. | 2003 Jan 3 |
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Exploration of in vitro pro-drug activation and futile cycling by glutathione S-transferases: thiol ester hydrolysis and inhibitor maturation. | 2003 Jun 15 |
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Coffee diterpenes prevent benzo[a]pyrene genotoxicity in rat and human culture systems. | 2003 Jun 27 |
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A novel Cl- inward-rectifying current in the plasma membrane of the calcifying marine phytoplankton Coccolithus pelagicus. | 2003 Mar |
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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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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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Ethacrynic acid can be effective for refractory congestive heart failure and ascites. | 2003 Nov |
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Desynchronization of electrically evoked auditory-nerve activity by high-frequency pulse trains of long duration. | 2003 Oct |
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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 |
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Characterization and molecular cloning of a glutathione S-transferase from the whitefly Bemisia tabaci (Hemiptera: Aleyrodidae). | 2004 Apr |
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Glutathione S-transferases and esterases in placenta after normal and pre-eclamptic pregnancies. | 2004 Apr |
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Inhibition of glucose-induced electrical activity in rat pancreatic beta-cells by DCPIB, a selective inhibitor of volume-sensitive anion currents. | 2004 Apr 5 |
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Controlled release of ethacrynic acid from poly(lactide-co-glycolide) films for glaucoma treatment. | 2004 Aug |
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The influence of anti-irritants on captopril hydrophilic gel. | 2004 Feb |
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Antioxidant gene therapy can protect hearing and hair cells from ototoxicity. | 2004 Feb |
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Transport of 99mTc-MAG3 via rat renal organic anion transporter 1. | 2004 Jan |
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Co-administration of kanamycin and ethacrynic acid as a deafening method for acute animal experiments. | 2004 Jan |
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Interactions of human organic anion transporters with diuretics. | 2004 Mar |
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
by
admin
on
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Thu Jul 06 23:12:54 UTC 2023
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Record UNII |
M5DP350VZV
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Record Status |
Validated (UNII)
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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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C485
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M5DP350VZV
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ETACRYNIC ACID
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M5DP350VZV
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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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DEGRADENT -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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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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