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Identification
NameEtacrynic acid
Accession NumberDB00903  (APRD00251)
TypeSmall Molecule
GroupsApproved
Description

A compound that 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. This compound has been classified as a loop or high ceiling diuretic. [PubChem]

Structure
Thumb
Synonyms
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid
acide étacrynique
ácido etacrínico
acidum etacrynicum
Etacrinic acid
Etakrinic acid
Ethacryinic Acid
Ethacrynate
Ethacrynic acid
Methylenebutyrylphenoxyacetic acid
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Edecrintablet25 mg/1oralKAISER FOUNDATION HOSPITALS2013-01-102016-04-23Us
Edecrintablet25 mgoralValeant Canada Lp Valeant Canada S.E.C.2004-10-15Not applicableCanada
Edecrintablet25 mg/1oralAvera Mc Kennan Hospital2015-10-022016-04-05Us
Edecrintablet25 mg/1oralAton Pharma, Inc.1967-01-102016-04-05Us
Edecrin Tab 50mgtablet50 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1968-12-312004-03-04Canada
Ethacrynic Sodiumpowder, for solution50 mg/50mLintravenousOceanside Pharmaceuticals1967-01-102016-04-05Us
Sodium Edecrinpowder for solution50 mgintravenousValeant Canada Lp Valeant Canada S.E.C.1968-12-31Not applicableCanada
Sodium Edecrinpowder, for solution50 mg/50mLintravenousAton Pharma, Inc.1967-01-102016-04-05Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ethacrynate Sodiuminjection, powder, for solution50 mg/50mLintravenousPar Pharmaceutical, Inc.2015-07-302016-04-05Us
Over the Counter ProductsNot Available
International Brands
NameCompany
CrinurylAssia
EdecrilMerck
EdecrinaNot Available
EndecrilNot Available
HidromedinNot Available
HydromedinMerck
MingitNot Available
OtacrilNot Available
ReomaxBioindustria
TaladrenMalesci
UregitNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ethacrynate sodium
ThumbNot applicableDBSALT001225
Categories
UNIIM5DP350VZV
CAS number58-54-8
WeightAverage: 303.138
Monoisotopic: 302.011264286
Chemical FormulaC13H12Cl2O4
InChI KeyInChIKey=AVOLMBLBETYQHX-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
SMILES
CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentPhenoxyacetic acid derivatives
Alternative Parents
Substituents
  • Phenoxyacetate
  • Butyrophenone
  • Phenylpropene
  • Acetophenone
  • Aryl ketone
  • Phenol ether
  • 1,2-dichlorobenzene
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Alkyl aryl ether
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Aryl halide
  • Aryl chloride
  • Vinylogous halide
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of high blood pressure and edema caused by diseases like congestive heart failure, liver failure, and kidney failure.
PharmacodynamicsEthacrynic 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.
Mechanism of actionEthacrynic 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.
Related Articles
AbsorptionOnset of action is rapid, usually within 30 minutes after an oral dose of ethacrynic acid or within 5 minutes after an intravenous injection of ethacrynic acid.
Volume of distributionNot Available
Protein binding> 98%
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOverdosage may lead to excessive diuresis with electrolyte depletion.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Ethacrynic Acid Action PathwayDrug actionSMP00097
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9591
Blood Brain Barrier-0.6921
Caco-2 permeable+0.5597
P-glycoprotein substrateSubstrate0.54
P-glycoprotein inhibitor INon-inhibitor0.5574
P-glycoprotein inhibitor IINon-inhibitor0.9828
Renal organic cation transporterNon-inhibitor0.9052
CYP450 2C9 substrateNon-substrate0.8508
CYP450 2D6 substrateNon-substrate0.8947
CYP450 3A4 substrateNon-substrate0.5262
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8384
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8344
BiodegradationReady biodegradable0.6545
Rat acute toxicity2.4505 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9228
hERG inhibition (predictor II)Non-inhibitor0.9044
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Aton pharma inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral25 mg/1
Tabletoral25 mg
Tabletoral50 mg
Injection, powder, for solutionintravenous50 mg/50mL
Powder for solutionintravenous50 mg
Powder, for solutionintravenous50 mg/50mL
Prices
Unit descriptionCostUnit
Sodium edecrin 50 mg vial527.4USD vial
Edecrin sodium 50 mg vial114.0USD vial
Ethacrynic acid 100% powder26.4USD g
Edecrin 25 mg tablet3.19USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point118.5-120.5Schultz, E.M. and Sprague, J.M.; U.S. Patent 3,255,241; June 7, 1966; assigned to Merck & co., Inc.
logP3.3Not Available
pKa3.5MERCK INDEX (2001)
Predicted Properties
PropertyValueSource
Water Solubility0.0194 mg/mLALOGPS
logP3.42ALOGPS
logP3.66ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.22 m3·mol-1ChemAxon
Polarizability28.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Schultz, E.M. and Sprague, J.M.; U.S. Patent 3,255,241; June 7, 1966; assigned to Merck
& co., Inc.

General ReferencesNot Available
External Links
ATC CodesC03CC01
AHFS Codes
  • 40:28.08
PDB EntriesNot Available
FDA labelDownload (75.2 KB)
MSDSDownload (74 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Ethacrynic acid.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethacrynic acid.
Acetylsalicylic acidAcetylsalicylic acid may decrease the diuretic activities of Ethacrynic acid.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Ethacrynic acid.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Ethacrynic acid.
AlfuzosinAlfuzosin may increase the hypotensive activities of Ethacrynic acid.
AllopurinolThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Allopurinol.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Ethacrynic acid.
AmifostineEthacrynic acid may increase the hypotensive activities of Amifostine.
AmikacinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Amikacin.
ArbekacinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Arbekacin.
BrimonidineBrimonidine may increase the antihypertensive activities of Ethacrynic acid.
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Ethacrynic acid.
ButabarbitalButabarbital may increase the hypotensive activities of Ethacrynic acid.
ButethalButethal may increase the hypotensive activities of Ethacrynic acid.
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Ethacrynic acid.
CaffeineThe risk or severity of adverse effects can be increased when Caffeine is combined with Ethacrynic acid.
CanagliflozinCanagliflozin may increase the hypotensive activities of Ethacrynic acid.
ChlorphenamineThe risk or severity of adverse effects can be increased when Chlorphenamine is combined with Ethacrynic acid.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethacrynic acid.
CisplatinEthacrynic acid may increase the nephrotoxic activities of Cisplatin.
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Ethacrynic acid.
ColesevelamColesevelam can cause a decrease in the absorption of Ethacrynic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclosporineThe risk or severity of adverse effects can be increased when Cyclosporine is combined with Ethacrynic acid.
DiazoxideDiazoxide may increase the hypotensive activities of Ethacrynic acid.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Ethacrynic acid.
DigoxinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Digoxin.
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Ethacrynic acid.
DofetilideEthacrynic acid may increase the QTc-prolonging activities of Dofetilide.
DuloxetineEthacrynic acid may increase the orthostatic hypotensive activities of Duloxetine.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Ethacrynic acid.
FludrocortisoneFludrocortisone may increase the hypokalemic activities of Ethacrynic acid.
FlunisolideFlunisolide may increase the hypokalemic activities of Ethacrynic acid.
FoscarnetThe serum concentration of Foscarnet can be increased when it is combined with Ethacrynic acid.
FosphenytoinFosphenytoin may decrease the diuretic activities of Ethacrynic acid.
FramycetinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Framycetin.
FurosemideFurosemide may increase the ototoxic activities of Ethacrynic acid.
GentamicinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Gentamicin.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Ethacrynic acid.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Ethacrynic acid.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Ethacrynic acid.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Ethacrynic acid.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Ethacrynic acid.
HexobarbitalHexobarbital may increase the hypotensive activities of Ethacrynic acid.
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Ethacrynic acid.
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Ethacrynic acid.
InfliximabInfliximab may decrease the diuretic activities of Ethacrynic acid.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Ethacrynic acid.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Ethacrynic acid.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Ethacrynic acid.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Ethacrynic acid.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Ethacrynic acid.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Ethacrynic acid.
IvabradineEthacrynic acid may increase the arrhythmogenic activities of Ivabradine.
KanamycinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Kanamycin.
LevodopaEthacrynic acid may increase the orthostatic hypotensive activities of Levodopa.
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Ethacrynic acid.
LicoriceLicorice may increase the hypokalemic activities of Ethacrynic acid.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Ethacrynic acid.
LithiumThe serum concentration of Lithium can be decreased when it is combined with Ethacrynic acid.
MecamylamineThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Mecamylamine.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Ethacrynic acid.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Ethacrynic acid.
MethohexitalMethohexital may increase the hypotensive activities of Ethacrynic acid.
MethotrexateThe therapeutic efficacy of Ethacrynic acid can be decreased when used in combination with Methotrexate.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Ethacrynic acid.
MolsidomineMolsidomine may increase the hypotensive activities of Ethacrynic acid.
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Ethacrynic acid.
MoxonidineMoxonidine may increase the hypotensive activities of Ethacrynic acid.
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Ethacrynic acid.
NeomycinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Neomycin.
NetilmicinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Netilmicin.
NicorandilNicorandil may increase the hypotensive activities of Ethacrynic acid.
ObinutuzumabEthacrynic acid may increase the hypotensive activities of Obinutuzumab.
OrciprenalineOrciprenaline may increase the hypokalemic activities of Ethacrynic acid.
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Ethacrynic acid.
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Ethacrynic acid.
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Ethacrynic acid.
PentobarbitalPentobarbital may increase the hypotensive activities of Ethacrynic acid.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Ethacrynic acid.
PerindoprilEthacrynic acid may increase the hypotensive activities of Perindopril.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Ethacrynic acid.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Ethacrynic acid.
PhenytoinPhenytoin may decrease the diuretic activities of Ethacrynic acid.
PrimidonePrimidone may increase the hypotensive activities of Ethacrynic acid.
ProbenecidThe risk or severity of adverse effects can be increased when Probenecid is combined with Ethacrynic acid.
QuinineQuinine may increase the hypotensive activities of Ethacrynic acid.
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Ethacrynic acid.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Ethacrynic acid.
RibostamycinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Ribostamycin.
RisperidoneThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Risperidone.
RituximabEthacrynic acid may increase the hypotensive activities of Rituximab.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Ethacrynic acid.
SecobarbitalSecobarbital may increase the hypotensive activities of Ethacrynic acid.
SpectinomycinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Spectinomycin.
StreptomycinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Streptomycin.
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Ethacrynic acid.
SulpirideThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Sulpiride.
TadalafilTadalafil may increase the antihypertensive activities of Ethacrynic acid.
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Ethacrynic acid.
TobramycinThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Tobramycin.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Ethacrynic acid.
TopiramateEthacrynic acid may increase the hypokalemic activities of Topiramate.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Ethacrynic acid.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Ethacrynic acid.
TreprostinilTreprostinil may increase the hypotensive activities of Ethacrynic acid.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Ethacrynic acid.
VardenafilVardenafil may increase the antihypertensive activities of Ethacrynic acid.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Ethacrynic acid.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Ethacrynic acid.
YohimbineYohimbine may decrease the antihypertensive activities of Ethacrynic acid.
Food Interactions
  • Take with food to reduce irritation.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Sodium:potassium:chloride symporter activity
Specific Function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume.
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular Weight:
121449.13 Da
References
  1. Bowes TJ, Gupta RS: Induction of mitochondrial fusion by cysteine-alkylators ethacrynic acid and N-ethylmaleimide. J Cell Physiol. 2005 Mar;202(3):796-804. [PubMed:15389563 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Ronquist G, Agren GK: A Mg2+- and Ca2+-stimulated adenosine triphosphatase at the outer surface of Ehrlich ascites tumor cells. Cancer Res. 1975 Jun;35(6):1402-6. [PubMed:124205 ]
  2. Proverbio F, Condrescu-Guidi M, Whittembury G: Ouabain-insensitive Na+ stimulation of an Mg-2+ -dependent ATPase in kidney tissue. Biochim Biophys Acta. 1975 Jun 25;394(2):281-92. [PubMed:124600 ]
  3. Valdes RM, Huff MO, El-Masri MA, El-Mallakh RS: Effect of ethacrynic acid on sodium pump alpha isoforms in SH-SY5Y cells. Bipolar Disord. 2003 Apr;5(2):123-8. [PubMed:12680902 ]
  4. Kiil F, Sejersted OM: Analysis of energy metabolism and mechanism of loop diuretics in the thick ascending limb of Henle's loop in dog kidneys. Acta Physiol Scand. 2003 May;178(1):73-82. [PubMed:12713517 ]
  5. Schurek HJ, Aulbert E, Ebel H, Muller-Suur C: Influence of ouabain and ethacrynic acid on sodium transport and NaK-ATPase activity in the isolated perfused rat kidney. Curr Probl Clin Biochem. 1975;4:162-8. [PubMed:127690 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Glutathione transferase activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA2
Uniprot ID:
P09210
Molecular Weight:
25663.675 Da
References
  1. Depeille P, Cuq P, Passagne I, Evrard A, Vian L: Combined effects of GSTP1 and MRP1 in melanoma drug resistance. Br J Cancer. 2005 Jul 25;93(2):216-23. [PubMed:15999103 ]
  2. Awasthi S, Srivastava SK, Ahmad F, Ahmad H, Ansari GA: Interactions of glutathione S-transferase-pi with ethacrynic acid and its glutathione conjugate. Biochim Biophys Acta. 1993 Jul 10;1164(2):173-8. [PubMed:8329448 ]
  3. Iersel ML, Ploemen JP, Struik I, van Amersfoort C, Keyzer AE, Schefferlie JG, van Bladeren PJ: Inhibition of glutathione S-transferase activity in human melanoma cells by alpha,beta-unsaturated carbonyl derivatives. Effects of acrolein, cinnamaldehyde, citral, crotonaldehyde, curcumin, ethacrynic acid, and trans-2-hexenal. Chem Biol Interact. 1996 Oct 21;102(2):117-32. [PubMed:8950226 ]
  4. van Iersel ML, Ploemen JP, Lo Bello M, Federici G, van Bladeren PJ: Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem Biol Interact. 1997 Dec 12;108(1-2):67-78. [PubMed:9463521 ]
  5. Morrow CS, Smitherman PK, Townsend AJ: Combined expression of multidrug resistance protein (MRP) and glutathione S-transferase P1-1 (GSTP1-1) in MCF7 cells and high level resistance to the cytotoxicities of ethacrynic acid but not oxazaphosphorines or cisplatin. Biochem Pharmacol. 1998 Oct 15;56(8):1013-21. [PubMed:9776312 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Bertucci C, Nanni B, Raffaelli A, Salvadori P: Chemical modification of human albumin at cys34 by ethacrynic acid: structural characterisation and binding properties. J Pharm Biomed Anal. 1998 Oct;18(1-2):127-36. [PubMed:9863950 ]
  2. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. [PubMed:9275312 ]
  3. Fehske KJ, Muller WE: High-affinity binding of ethacrynic acid is mediated by the two most important drug binding sites of human serum albumin. Pharmacology. 1986;32(4):208-13. [PubMed:3714803 ]
  4. Lebedev AA, Samokrutova OV: [Study of the binding of diuretics by serum proteins according to changes in tryptophan fluorescence]. Farmakol Toksikol. 1989 May-Jun;52(3):40-3. [PubMed:2792351 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 25, 2016 14:08