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Drug-Target Interaction

Drug

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PubChem ID:3278
Structure:
Synonyms:
(2,3-Dichloro-4-(2-ethylacryloyl)phenoxy)acetic acid
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid
(2,3-Dichloro-4-(2-methylenebutyryl)phenoxy)acetic acid
(2,3-Dichloro-4-[2-methylenebutyryl]phenoxy)acetic acid
(4-(2-Methylenebutyryl)-2,3-dichlorophenoxy)acetic acid
1gsf
2, 3-Dichloro-4-(2-methylenebutyl)phenoxyacetic acid
2, 3-Dichloro-4-(2-methylenebutyryl)phenoxyacetic acid
2,3-Dichloro-4(2-methylene- butyryl)phenoxy] acetic acid
2,3-Dichloro-4-(2-methylenebutyl)phenoxyacetic acid
2,3-Dichloro-4-(2-methylenebutyryl)phenoxy acetic acid
2,3-Dichloro-4-(2-methylenebutyryl)phenoxyacetic acid
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
2gss
58-54-8
6500-81-8
6500-81-8 (hydrochloride salt)
AB00051988
AC1L1FKN
Acetic acid, (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-
Acetic acid, (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)-
Acetic acid, [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-
Acetic acid, [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]-
Acetic acid, {[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-}
Acetic acid, {[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]-}
Acide etacrynique
Acide etacrynique [INN-French]
Acido etacrinico
Acido etacrinico [INN-Spanish]
Acidum etacrynicum
Acidum etacrynicum [INN-Latin]
AIDS-159968
AIDS159968
AKOS003404732
bmse000134
BPBio1_000086
BRD-K63630713-001-05-0
BRN 1915060
BSPBio_000078
BSPBio_002010
C13H12Cl2O4
CAS-58-54-8
CCG-38915
CCRIS 4638
CHEBI:4876
CHEMBL456
CPD000058600
Crinuryl
D00313
DB00903
DivK1c_000900
E0526
E4754_FLUKA
E4754_SIGMA
EAA
Edecril
Edecrin
Edecrina
EINECS 200-384-1
Endecril
Etacrinic acid
Etacrynic acid
Etacrynic acid (JP15/INN)
Etacrynic acid (JP16/INN)
Etakrinic acid
Ethacrinic Acid
Ethacrinique (acide)
Ethacryinic Acid
Ethacrynate
Ethacrynic Acid
Ethacrynic acid (USP)
Ethacrynic acid [USAN:BAN]
Ethacrynic Acid, Sodium Salt
Hidromedin
HMS1568D20
HMS1920M16
HMS2089N17
HMS2091D17
HMS2095D20
HMS3259G03
HMS502M22
HSDB 2136
Hydromedin
IDI1_000900
KBio1_000900
KBio2_001293
KBio2_003861
KBio2_006429
KBio3_001230
KBioGR_001207
KBioSS_001293
Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova
Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova [Czech]
Kyselina ethakrynova
Kyselina ethakrynova [Czech]
LS-240
Methylenebutyryl phenoxyacetic acid
Methylenebutyrylphenoxyacetic acid
Mingit
MK 595
MK-595
MLS000069535
MLS002701928
NCGC00016260-01
NCGC00016260-02
NCGC00016260-03
NCGC00016260-04
NCGC00016260-05
NCGC00016260-06
NCGC00016260-07
NCGC00016260-08
NCGC00016260-09
NCGC00016260-10
NCGC00016260-11
NCGC00022601-03
NCGC00022601-04
NCGC00022601-05
NCI60_041898
NINDS_000900
NSC 624008
NSC 85791
NSC624008
NSC85791
Otacril
Prestwick0_000259
Prestwick1_000259
Prestwick2_000259
Prestwick3_000259
Prestwick_671
Reomax
SAM002264611
SBB064161
SMR000058600
SPBio_000054
SPBio_002297
SPECTRUM1500287
Spectrum2_000097
Spectrum3_000425
Spectrum4_000544
Spectrum5_000680
Spectrum_000813
Taladren
UNII-M5DP350VZV
Uregit
WLN: QV1OR BG CG DVY2&U1
[2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid
[2,3-dichloro-4-(2-methylenebutanoyl)phenoxy]acetic acid
[2,3-Dichloro-4-(2-methylenebutyryl)phenoxy]acetic acid
[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
[4-(2-Methylenebutyryl)-2,3-dichlorophenoxy]acetic acid
{[2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic} acid
{[2,} 3-Dichloro-4-(2-methylenebutyryl)phenoxy\]acetic acid
{[2,} 3-dichloro-4-(2-methylenebutyryl)phenoxy]acetic acid
{[4-(2-Methylenebutyryl)-2,3-dichlorophenoxy]acetic} acid
ATC-Codes:
Side-Effects:
Side-EffectFrequency
gout0
fatigue0
liver function tests abnormal0
convulsions0
vertigo0
diarrhea0
tinnitus0
vomiting0
gastrointestinal hemorrhage0
pain0
dysphagia0
nausea0
anorexia0
malaise0
headache0
agranulocytosis0
hypoglycemia0
hyperuricemia0
rash0
acute pancreatitis0
jaundice0
rheumatic carditis0
deafness0
hematuria0
fever0
blurred vision0
chills0
purpura0
thrombocytopenia0
confusion0
hyperglycemia0
neutropenia0
apprehension0

Target

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Uniprot ID:Q9UE37_HUMAN
Synonyms:
Glutathione transferase
EC-Numbers:2.5.1.18
Organism:Homo sapiens
Human
PDB IDs:-

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----
----

References:

14556662
Characterization of cell death induced by ethacrynic acid in a human colon cancer cell line DLD-1 and suppression by N-acetyl-L-cysteine.. Shu Aizawa; Keizou Ookawa; Toshihiro Kudo; Junpei Asano; Makoto Hayakari; Shigeki Tsuchida (2003) Cancer science display abstract
Since ethacrynic acid (EA), an SH modifier as well as glutathione S-transferase (GST) inhibitor, has been suggested to induce apoptosis in some cell lines, its effects on a human colon cancer cell line DLD-1 were examined. EA enhanced cell proliferation at 20-40 microM, while it caused cell death at 60-100 microM. Caspase inhibitors did not block cell death and DNA ladder formation was not detected. Poly(ADP-ribose) polymerase, however, was cleaved into an 82-kDa fragment, different from an 85-kDa fragment that is specific for apoptosisis. The 82-kDa fragment was not recognized by antibody against PARP fragment cleaved by caspase 3. N-Acetyl-L-cysteine (NAC) completely inhibited EA-induced cell death, but 3(2)-t-butyl-4-hydroxyanisole or pyrrolidinedithiocarbamate ammonium salt did not. Glutathione (GSH) levels were dose-dependently increased in cells treated with EA and this increase was hardly affected by NAC addition. Mitogen-activated protein kinase (MAPK) kinase (MEK) 1, extracellular signal-regulated kinase (ERK) 1 and GST P1-1 were increased in cells treated with 25-75 microM EA, while c-Jun N-terminal kinase (JNK) 1 and p38 MAPK were markedly decreased by 100 microM EA. NAC repressed EA-induced alterations in these MAPKs and GST P1-1. p38 MAPK inhibitors, SB203580 and FR167653, dose-dependently enhanced EA-induced cell death. An MEK inhibitor, U0126, did not affect EA-induced cell death. These studies revealed that EA induced cell death concomitantly with a novel PARP fragmentation, but without DNA fragmentation. p38 MAPK was suggested to play an inhibitory role in EA-induced cell death.
8442764
Isoenzyme selective irreversible inhibition of rat and human glutathione S-transferases by ethacrynic acid and two brominated derivatives.. J H Ploemen; J J Bogaards; G A Veldink; B van Ommen; D H Jansen; P J van Bladeren (1993) Biochemical pharmacology display abstract
In the present study it has been shown that ethacrynic acid can inhibit glutathione S-transferase (GST) of the pi-class irreversibly. [14C]Ethacrynic acid, 0.8 nmol/nmol human P1-1 and 0.8 nmol/nmol rat GST 7-7 could be incorporated, resulting in 65-93% inhibition of the activity towards 1-chloro-2,4-dinitrobenzene (CDNB). Isoenzymes of the alpha- and mu-class also bound [14C]ethacrynic acid, however without loss of catalytic activity. Incorporation ranged from 0.3 to 0.6 and 0.2 nmol/nmol enzyme for the mu- and alpha-class GST isoenzymes, respectively. For all isoenzymes, incorporation of [14C]ethacrynic acid could be prevented by preincubation with tetrachloro-1,4-benzoquinone, suggesting, that a cysteine residue is the target site. Protection of GST P1-1 against inhibition by ethacrynic acid by the substrate analog S-hexylglutathione, indicates an active site-directed modification. The monobromo and dibromo dihydro derivatives of ethacrynic acid were synthesized in an effort to produce more reactive compounds. The monobromo derivative did not exhibit enhanced irreversible inhibitory capacity. However, the dibromo dihydro derivative inhibited both human and rat GST isoenzymes of the pi-class very efficiently, resulting in 90-96% inhibition of the activity towards CDNB. Interestingly, this compound is also a powerful irreversible inhibitor of the mu-class GST isoenzymes, resulting in 52-70% inhibition. The two bromine atoms only marginally affect the strong (reversible) competitive inhibitory capacity of ethacrynic acid, with IC50 (microM) of 0.4-0.6 and 4.6-10 for the mu- and pi-class GST isoenzymes, respectively.