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Details

Stereochemistry ACHIRAL
Molecular Formula C13H12Cl2O4
Molecular Weight 303.138
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHACRYNIC ACID

SMILES

CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl

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)

HIDE SMILES / InChI

Molecular Formula C13H12Cl2O4
Molecular Weight 303.138
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Ethacrynic acid-induced convulsions and brain neurotransmitters in mice.
1992 Oct 6
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
Chinchilla models of selective cochlear hair cell loss.
2002 Dec
Rapid spectrophotometric method for serum glutathione S-transferases activity.
2002 Dec
Effects of glutathione S-transferase inhibitors on nitroglycerin action in pig isolated coronary arteries.
2002 Dec
Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells.
2002 Jul 12
[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
Combined effects of cadmium and nickel on testicular xenobiotic metabolizing enzymes in rats.
2002 Nov
Inhibition of the multidrug resistance protein 1 (MRP1) by peptidomimetic glutathione-conjugate analogs.
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
Induction of cytosolic glutathione S-transferases from Atlantic eel (Anguilla Anguilla) after intraperitoneal treatment with polychlorinated biphenyls.
2002 Oct 7
Interaction between metamizol and tramadol in a model of acute visceral pain in rats.
2003
Effect of ethacrynic acid on sodium pump alpha isoforms in SH-SY5Y cells.
2003 Apr
Dopamine-induced oxidative stress in neurons with glutathione deficit: implication for schizophrenia.
2003 Aug 1
Changes in cell proliferation in rat and guinea pig cochlea after aminoglycoside-induced damage.
2003 Aug 28
Interplay between MRP inhibition and metabolism of MRP inhibitors: the case of curcumin.
2003 Dec
Cytosolic and mitochondrial glutathione in microglial cells are differentially affected by oxidative/nitrosative stress.
2003 Feb
Substrate specificity of mouse aldo-keto reductase AKR7A5.
2003 Feb 1
Ethacrynic acid and the sulfa-sensitive patient.
2003 Jan 13
Engineering a new C-terminal tail in the H-site of human glutathione transferase P1-1: structural and functional consequences.
2003 Jan 3
Exploration of in vitro pro-drug activation and futile cycling by glutathione S-transferases: thiol ester hydrolysis and inhibitor maturation.
2003 Jun 15
Coffee diterpenes prevent benzo[a]pyrene genotoxicity in rat and human culture systems.
2003 Jun 27
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 an ectonucleoside triphosphate diphosphohydrolase 1 activity in alkaline phosphatase-depleted rat osseous plate membranes: possible functional involvement in the calcification process.
2003 Mar 21
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
Ethacrynic acid can be effective for refractory congestive heart failure and ascites.
2003 Nov
Late dosing with ethacrynic acid can reduce gentamicin concentration in perilymph and protect cochlear hair cells.
2003 Nov
Improved neural representation of vowels in electric stimulation using desynchronizing pulse trains.
2003 Oct
Desynchronization of electrically evoked auditory-nerve activity by high-frequency pulse trains of long duration.
2003 Oct
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
Antioxidant gene therapy can protect hearing and hair cells from ototoxicity.
2004 Feb
Risk of hospitalization for upper gastrointestinal tract bleeding.
2004 Jan
Transport of 99mTc-MAG3 via rat renal organic anion transporter 1.
2004 Jan
Co-administration of kanamycin and ethacrynic acid as a deafening method for acute animal experiments.
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
Interactions of human organic anion transporters with diuretics.
2004 Mar
Cellular glutathione prevents cytolethality of monomethylarsonic acid.
2004 Mar 1
Patents

Sample Use Guides

In Vivo Use Guide
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
Ethacrynic acid (10uM) induced both apoptosis and necroptosis in primary CLL cells.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:46:15 UTC 2019
Edited
by admin
on Tue Oct 22 00:46:15 UTC 2019
Record UNII
M5DP350VZV
Record Status Validated (UNII)
Record Version
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Name Type Language
ETHACRYNIC ACID
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
(2,3-DICHLORO-4-(2-METHYLENEBUTYRYL)PHENOXY)ACETIC ACID
Systematic Name English
ETHACRYNIC ACID [USAN]
Common Name English
ETHACRYNIC ACID [HSDB]
Common Name English
2-(2,3-DICHLORO-4-(2-METHYLENE-1-OXOBUTYL)PHENOXY)ACETIC ACID
Systematic Name English
MK-595
Code English
4-(METHYLENEBUTYRYL)-2,3-DICHLOROPHENOXY)ACETIC ACID
Common Name English
ACETIC ACID, (2,3-DICHLORO-4-(2-METHYLENE-1-OXOBUTYL)PHENOXY)-
Common Name English
2,3-DICHLORO-4-(2-METHYLENEBUTYRYL)PHENOXY)ACETATE
Common Name English
ETACRYNIC ACID [WHO-DD]
Common Name English
NSC-85791
Code English
ETHACRYNIC ACID [USP]
Common Name English
ETHACRYNIC ACID [MI]
Common Name English
ETACRYNIC ACID [INN]
Common Name English
ETACRYNIC ACID [MART.]
Common Name English
ETHACRYNIC ACID [VANDF]
Common Name English
ETHACRYNATE
Common Name English
ETHACRYNIC ACID [ORANGE BOOK]
Common Name English
NSC-624008
Code English
EDECRIN
Brand Name English
ETHACRYNIC ACID [USP-RS]
Common Name English
ETACRYNIC ACID [EP]
Common Name English
ETACRYNIC ACID
EP   INN   MART.   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C49184
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
WHO-VATC QC03CC01
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
WHO-ATC C03CC01
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
LIVERTOX 380
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
NDF-RT N0000175590
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
NDF-RT N0000175366
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
Code System Code Type Description
HSDB
58-54-8
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
INN
1651
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
DRUG BANK
DB00903
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
NCI_THESAURUS
C485
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
RXCUI
62349
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
ALTERNATIVE
ECHA (EC/EINECS)
200-384-1
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
IUPHAR
7179
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
MESH
D004976
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
WIKIPEDIA
ETACRYNIC ACID
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
CAS
58-54-8
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
ChEMBL
CHEMBL456
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
EVMPD
SUB07255MIG
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
PUBCHEM
3278
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
RXCUI
4109
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
MERCK INDEX
M5042
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY Merck Index
EPA CompTox
58-54-8
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
LactMed
58-54-8
Created by admin on Tue Oct 22 00:46:15 UTC 2019 , Edited by admin on Tue Oct 22 00:46:15 UTC 2019
PRIMARY
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