Page last updated: 2024-08-02 02:55:04

b 1287

Description

E5564: structure in first source [MeSH]

eritoran tetrasodium : An organic sodium salt which is the tetrasodium salt of eritoran. [CHeBI]

Cross-References

ID SourceID
PubMed CID6450173
CHEMBL ID3301672
CHEBI ID46692
MeSH IDM0297733

Synonyms (32)

Synonym
eritoran sodium
fuo195tc7o ,
e 5564
eritoran tetrasodium [usan]
unii-fuo195tc7o
b1287 saccharide
eritoran tetrasodium
e-5564
b-1287 ,
185954-98-7
D04043
e5564
eritoran tetrasodium (usan)
tetrasodium 3-o-decyl-2-deoxy-6-o-{2-deoxy-3-o-[(3r)-3-methoxydecyl]-6-o-methyl-2-[(11z)-octadec-11-enoylamino]-4-o-phosphonato-beta-d-glucopyranosyl}-2-[(3-oxotetradecanoyl)amino]-1-o-phosphonato-alpha-d-glucopyranose
CHEBI:46692 ,
alpha-d-glucopyranose, 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-(((11z)-1-oxo-11-octadecenyl)amino)-4-o-phosphono-beta-d-glucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-, 1-(dihydrogen phosphate), tetrasodium salt
3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-((11z)-octadec-11-enoylamino)-4-o-phosphonato-beta-d-glucopyranosyl)-2-((3-oxotetradecanoyl)amino)-alpha-d-glucopyranosyl tetrasodium phosphate
alpha-d-glucopyranose, 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-(((11z)-1-oxo-11-octadecenyl)amino)-4-o-phosphono-beta-d-glucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-,1-(dihydrogen phosphate), tetrasodium salt
b1287 ,
tetrasodium [(2r,3r,4r,5s,6r)-4-decoxy-5-hydroxy-6-[[(2r,3r,4r,5s,6r)-4-[(3r)-3-methoxydecoxy]-6-(methoxymethyl)-3-[[(z)-octadec-11-enoyl]amino]-5-phosphonatooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] phosphate
.alpha.-d-glucopyranose, 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-(((11z)-1-oxo-11-octadecenyl)amino)-4-o-phosphono-.beta.-d-glucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-, 1-(dihydrogen phosphate), tetrasodium salt
3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-((11z)-octadec-11-enoylamino)-4-o-phosphonato-.beta.-d-glucopyranosyl)-2-((3-oxotetradecanoyl)amino)-.alpha.-d-glucopyranosyl tetrasodium phosphate
eritoran tetrasodium salt
eritoran tetrasodium [who-dd]
1029325-41-4
eritoran tetrasodium salt [mi]
eritoran sodium [jan]
CHEMBL3301672
185954-98-7 (tetrasodium)
Q27120680
EX-A5459
tetrasodium;[(2r,3r,4r,5s,6r)-4-decoxy-5-hydroxy-6-[[(2r,3r,4r,5s,6r)-4-[(3r)-3-methoxydecoxy]-6-(methoxymethyl)-3-[[(z)-octadec-11-enoyl]amino]-5-phosphonatooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] phosphate

Drug Classes (1)

ClassDescription
organic sodium salt

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (2.56)18.2507
2000's23 (58.97)29.6817
2010's15 (38.46)24.3611
2020's0 (0.00)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (15.38%)5.53%
Reviews2 (5.13%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other31 (79.49%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
meclofenamate sodium anhydrousorganic sodium salt00low000000
4-phenylbutyric acid, sodium saltorganic sodium saltEC 3.5.1.98 (histone deacetylase) inhibitor;
geroprotector;
neuroprotective agent;
orphan drug;
prodrug
00low000000
sodium citrate, anhydrousorganic sodium saltanticoagulant;
flavouring agent
00low000000
sulfobromophthalein sodiumorganic sodium saltdye00low000000
suramin sodiumorganic sodium saltangiogenesis inhibitor;
antinematodal drug;
antineoplastic agent;
apoptosis inhibitor;
EC 2.7.11.13 (protein kinase C) inhibitor;
GABA antagonist;
GABA-gated chloride channel antagonist;
purinergic receptor P2 antagonist;
ryanodine receptor agonist;
trypanocidal drug
00low000000
evans blueorganic sodium saltfluorochrome;
histological dye;
sodium channel blocker;
teratogenic agent
00low000000
sodium carbonatecarbonate salt;
organic sodium salt
00low000000
eosine yellowish-(ys)organic sodium salt;
organobromine compound
fluorochrome;
histological dye
00low000000
fast green fcforganic sodium saltfluorochrome;
food colouring;
histological dye
00low000000
dexamethasone sodium phosphateorganic sodium saltglucocorticoid receptor agonist00low000000
red 2gorganic sodium salthistological dye00low000000
biebrich scarletorganic sodium salthistological dye00low000000
chromotrope 2rorganic sodium salthistological dye00low000000
carbenicillin disodiumorganic sodium salt00low000000
light green sforganic sodium salthistological dye00low000000
brilliant croceinorganic sodium salthistological dye00low000000
etidronate disodiumorganic sodium saltantineoplastic agent;
bone density conservation agent;
chelator
00low000000
sytroniron chelate;
organic sodium salt
00low000000
cromolyn sodiumorganic sodium saltanti-asthmatic drug;
drug allergen
00low000000
clodronate disodiumone-carbon compound;
organic sodium salt
bone density conservation agent00low000000
foscarnet sodiumone-carbon compound;
organic sodium salt
antiviral drug00low000000
pyranineorganic sodium saltfluorochrome00low000000
betamethasone sodium phosphateorganic sodium salt;
tertiary alpha-hydroxy ketone
00low000000
c.i. direct red 80organic sodium saltfluorochrome;
histological dye
00low000000
disodium alpha-sulfobenzylpenicillinorganic sodium salt00low000000
estramustine phosphate sodiumorganic sodium salt00low000000
sodium thiocyanateorganic sodium salt00low000000
sodium bicarbonateone-carbon compound;
organic sodium salt
antacid;
food anticaking agent
00low000000
sodium acetate, anhydrousorganic sodium saltNMR chemical shift reference compound00low000000
sodium benzoateorganic sodium saltalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
00low000000
dipyroneorganic sodium saltanti-inflammatory agent;
antipyretic;
antirheumatic drug;
cyclooxygenase 3 inhibitor;
non-narcotic analgesic;
peripheral nervous system drug;
prodrug
00low000000
formic acid, sodium saltorganic sodium saltastringent;
buffer
00low000000
sodium propionateorganic sodium saltantifungal drug;
food preservative
00low000000
ponceau sorganic sodium salt;
organosulfonate salt
fluorochrome;
histological dye
00low000000
sodium ethoxideorganic sodium saltnucleophilic reagent00low000000
nabamdithiocarbamate salt;
organic sodium salt
antifungal agrochemical00low000000
sodium dodecyl sulfateorganic sodium saltdetergent;
protein denaturant
00low000000
chloramine-torganic sodium saltallergen;
antifouling biocide;
disinfectant
00low000000
primulineorganic sodium salt;
organosulfonate salt
fluorochrome;
histological dye
00low000000
metanil yelloworganic sodium salthistological dye00low000000
alizarin red sorganic sodium salt;
organosulfonate salt
histological dye00low000000
diclofenac sodiumorganic sodium salt00low000000
sodium butyrateorganic sodium saltEC 3.5.1.98 (histone deacetylase) inhibitor;
geroprotector
00low000000
sulfacetamide sodiumhydrate;
organic sodium salt
antiinfective agent;
antimicrobial agent;
EC 2.5.1.15 (dihydropteroate synthase) inhibitor
00low000000
lasalocid sodiumbenzoates;
organic sodium salt
coccidiostat;
ionophore
00low000000
lissamine rhodamine borganic sodium saltfluorescent probe;
fluorochrome;
histological dye
00low000000
cefotaxime sodiumorganic sodium salt00low000000
l 749345organic sodium saltantibacterial drug00low000000
thiopental sodiumorganic sodium saltintravenous anaesthetic00low000000
eosine i bluishorganic sodium saltfluorescent dye;
histological dye
00low000000
rabeprazole sodiumorganic sodium salt00low000000
pantoprazole sodiumorganic sodium saltanti-ulcer drug;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
00low000000
azocarmine gorganic sodium salthistological dye00low000000
pravastatin sodiumorganic sodium salt;
statin (semi-synthetic)
anticholesteremic drug00low000000
valproate sodiumorganic sodium saltgeroprotector00low000000
tazobactam sodiumorganic sodium saltantiinfective agent;
antimicrobial agent;
EC 3.5.2.6 (beta-lactamase) inhibitor
00low000000
cilastatin sodiumorganic sodium saltEC 3.4.13.19 (membrane dipeptidase) inhibitor;
protease inhibitor
00low000000
beraprost sodiumorganic sodium saltanti-inflammatory agent;
antihypertensive agent;
platelet aggregation inhibitor;
prostaglandin receptor agonist;
vasodilator agent
00low000000
tofisopamorganic sodium saltantipyretic;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug
00low000000
azuletil sodiumorganic sodium salt;
organosulfonate salt
anti-ulcer drug;
thromboxane A2 antagonist
00low000000
brequinar sodiumorganic sodium saltanticoronaviral agent;
antimetabolite;
antineoplastic agent;
antiviral agent;
EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor;
immunosuppressive agent;
pyrimidine synthesis inhibitor
00low000000
sri 62320organic sodium salt;
statin (synthetic)
00low000000
methylprednisolone suleptanateorganic sodium saltanti-asthmatic drug;
anti-inflammatory agent;
glucocorticoid receptor agonist;
prodrug
00low000000
ampicillin sodiumorganic sodium salt00low000000
cerivastatin sodiumorganic sodium salt;
statin (synthetic)
00low000000
montelukast sodiumorganic sodium salt00low000000
cyanotriphenylborateorganic sodium salt;
tetraorganoborate salt
00low000000
thiopental sodiumorganic sodium saltintravenous anaesthetic00low000000
ahr 5850organic sodium saltcyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor
00low000000
cefamandole nafateorganic sodium saltantibacterial drug;
prodrug
00low000000
cytomelorganic sodium salt00low000000
letterorganic sodium salt00low000000
sodium lactatelactate salt;
organic sodium salt
food acidity regulator;
food preservative
00low000000
cefmetazole sodiumorganic sodium saltantimicrobial agent00low000000
piperacillin sodiumorganic sodium salt00low000000
methicillin sodiumorganic sodium salt00low000000
dicloxacillin sodiumorganic sodium salt00low000000
nafcillin sodiumorganic sodium salt00low000000
oxacillin sodiumorganic sodium salt00low000000
sodium cholatecholate salt;
organic sodium salt
00low000000
penicillin g sodiumorganic sodium salt00low000000
cefamandole nafateorganic sodium saltantibacterial drug00low000000
sodium diatrizoateorganic sodium salt;
organoiodine compound
radioopaque medium00low000000
docusate sodiumorganic sodium salt00low000000
phenobarbital sodiumbarbiturates;
organic sodium salt
00low000000
cephapirin sodiumcephalosporin;
organic sodium salt
antibacterial drug00low000000
cloxacillin sodiumorganic sodium salt00low000000
sodium cephalothinorganic sodium salt00low000000
cefazolin sodiumorganic sodium salt00low000000
tolmetin sodiumhydrate;
organic sodium salt
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-steroidal anti-inflammatory drug
00low000000
nuclear fast redorganic sodium saltfluorochrome;
histological dye
00low000000
fractalsorganic sodium salt;
statin (synthetic)
00low000000
prednisolone sodium succinateorganic sodium saltanti-inflammatory drug00low000000
naproxen sodiumorganic sodium saltantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug
00low000000
alendronate sodiumhydrate;
organic sodium salt
bone density conservation agent;
EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor
00low000000
azlocillin sodiumorganic sodium salt00low000000
nafcillin sodiumhydrate;
organic sodium salt
00low000000
nxl 104organic sodium saltantibacterial drug;
antimicrobial agent;
EC 3.5.2.6 (beta-lactamase) inhibitor
00low000000
methampicillin, monosodium salt, (2s-(2alpha,5alpha,6beta(s*)))-isomerorganic sodium salt00low000000
ssr128129eorganic sodium saltantineoplastic agent;
fibroblast growth factor receptor antagonist
00low000000
8-bromocyclic gmp, sodium saltorganic sodium saltmuscle relaxant;
protein kinase G agonist
00low000000
dy-676organic sodium saltfluorochrome00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
chlorpromazineorganochlorine compound;
phenothiazines;
tertiary amine
anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
phenothiazine antipsychotic drug
2000200024.0low001000
fluphenazineN-alkylpiperazine;
organofluorine compound;
phenothiazines
anticoronaviral agent;
dopaminergic antagonist;
phenothiazine antipsychotic drug
2000200024.0low001000
lidocainebenzenes;
monocarboxylic acid amide;
tertiary amino compound
anti-arrhythmia drug;
drug allergen;
environmental contaminant;
local anaesthetic;
xenobiotic
2000200024.0low001000
s-methylisothiopseudouronium2006200618.0low000100
trifluoperazineN-alkylpiperazine;
N-methylpiperazine;
organofluorine compound;
phenothiazines
antiemetic;
calmodulin antagonist;
dopaminergic antagonist;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor;
phenothiazine antipsychotic drug
2000200024.0low001000
acetylcysteineacetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid
antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
2014201410.0low000010
manganeseelemental manganese;
manganese group element atom
Escherichia coli metabolite;
micronutrient
2004200420.0low000100
acetylglucosamineN-acetyl-D-glucosamineepitope2013201311.0low000010
galactosamineD-galactosamine;
primary amino compound
toxin2009201014.5low000200
isothiuronium2006200618.0low000100
glucosamineD-glucosamineEscherichia coli metabolite;
geroprotector;
mouse metabolite
201820186.0low000010
bilirubinbiladienes;
dicarboxylic acid
antioxidant;
human metabolite;
mouse metabolite
2009201014.5low000200
e 55312000200024.0low001000
mocetinostataminopyrimidine;
benzamides;
pyridines;
secondary amino compound;
secondary carboxamide;
substituted aniline
antineoplastic agent;
apoptosis inducer;
autophagy inducer;
cardioprotective agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
hepatotoxic agent
2014201410.0low000010
lipid adodecanoate ester;
lipid A;
tetradecanoate ester
Escherichia coli metabolite1999201916.2high60225120
ro13-99042014201410.0low000010
crx-526201820186.0medium000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Acute Hepatic Failure02009201014.5low000200
Acute Lung Injury02014201410.0low000010
Acute Respiratory Distress Syndrome0201820186.0low000010
Airflow Obstruction, Chronic0201820186.0low000010
Airway Hyper-Responsiveness02005200519.0low000100
Asthma0201820186.0low000010
Asthma, Bronchial0201820186.0low000010
Bacterial Disease02010201014.0low100100
Bacterial Infections02010201014.0low100100
Bacterial Infections, Gram-Negative02006200618.0low000100
Blood Poisoning02004201415.7low200510
Body Weight0201520159.0low000010
Brain Ischemia0201920195.0low000010
Cardiomyopathies02006200618.0low000100
Cardiomyopathies, Primary02006200618.0low000100
Cerebral Ischemia0201920195.0low000010
Cirrhosis, Liver02003200321.0low100100
Complication, Postoperative02007200717.0low100100
Critical Illness02010201014.0low200200
Diabetes Mellitus0201820186.0low000010
Disease Models, Animal02002201913.9low000530
E coli Infections02006201414.0low000110
Endotoxemia02003200819.0low200500
Endotoxin Shock02003200420.5low000200
Enterocolitis, Necrotizing02013201311.0low000010
Escherichia coli Infections02006201414.0low000110
Experimental Lung Inflammation02005200519.0low000100
Gram-Negative Bacterial Infections02006200618.0low000100
Grippe02014201410.0low000010
Hemorrhagic Shock02014201410.0low000010
Infections, Orthomyxoviridae02014201410.0low000010
Infections, Pseudomonas02013201311.0low000010
Infections, Respiratory Syncytial Virus02012201212.0low000010
Inflammation02001201812.8low000130
Influenza, Human02014201410.0low000010
Injuries, Soft Tissue02014201410.0low000010
Injury, Ischemia-Reperfusion02012201212.0low000010
Innate Inflammatory Response02001201812.8low000130
Insulin Resistance0201520159.0low000010
Insulin Sensitivity0201520159.0low000010
Ischemia02012201212.0low000010
Liver Cirrhosis02003200321.0low100100
Liver Failure, Acute02009201014.5low000200
Lung Injury, Acute02014201410.0low000010
Necrotizing Enterocolitis02013201311.0low000010
Obesity0201520159.0low000010
Orthomyxoviridae Infections02014201410.0low000010
Periphlebitis02008200816.0low000100
Peritonitis02014201410.0low000010
Phlebitis02008200816.0low000100
Pneumonia02005200519.0low000100
Postoperative Complications02007200717.0low100100
Primary Peritonitis02014201410.0low000010
Pseudomonas Infections02013201311.0low000010
Pulmonary Disease, Chronic Obstructive0201820186.0low000010
Reperfusion Injury02012201212.0low000010
Respiratory Distress Syndrome0201820186.0low000010
Respiratory Syncytial Virus Infections02012201212.0low000010
Sensitivity and Specificity01999199925.0low001000
Sepsis12004201415.7low200510
Shock, Septic02003200420.5low000200
Tachyarrhythmia02004200420.0low100100
Tachycardia02004200420.0low100100

Safety/Toxicity (1)

ArticleYear
Safety, pharmacokinetics, pharmacodynamics, and plasma lipoprotein distribution of eritoran (E5564) during continuous intravenous infusion into healthy volunteers.
Antimicrobial agents and chemotherapy, , Volume: 48, Issue:9
2004

Pharmacokinetics (6)

ArticleYear
TLR4 inhibition impairs bacterial clearance in a therapeutic setting in murine abdominal sepsis.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], , Volume: 63, Issue:11
2014
Continuous pharmacodynamic activity of eritoran tetrasodium, a TLR4 antagonist, during intermittent intravenous infusion into normal volunteers.
Innate immunity, , Volume: 14, Issue:6
2008
Safety, pharmacokinetics, pharmacodynamics, and plasma lipoprotein distribution of eritoran (E5564) during continuous intravenous infusion into healthy volunteers.
Antimicrobial agents and chemotherapy, , Volume: 48, Issue:9
2004
LPS binding protein does not participate in the pharmacokinetics of E5564.
Journal of endotoxin research, , Volume: 10, Issue:3
2004
Pharmacokinetics of E5564, a lipopolysaccharide antagonist, in patients with impaired hepatic function.
Journal of clinical pharmacology, , Volume: 43, Issue:12
2003
Extended in vivo pharmacodynamic activity of E5564 in normal volunteers with experimental endotoxemia [corrected].
The Journal of pharmacology and experimental therapeutics, , Volume: 308, Issue:1
2004

Dosage (6)

ArticleYear
Continuous pharmacodynamic activity of eritoran tetrasodium, a TLR4 antagonist, during intermittent intravenous infusion into normal volunteers.
Innate immunity, , Volume: 14, Issue:6
2008
Effective dosing of lipid A analogue E5564 in rats depends on the timing of treatment and the route of Escherichia coli infection.
The Journal of infectious diseases, , Mar-01, Volume: 193, Issue:5
2006
Toll-like receptor 4 antagonist (E5564) prevents the chronic airway response to inhaled lipopolysaccharide.
American journal of physiology. Lung cellular and molecular physiology, , Volume: 289, Issue:2
2005
Extended in vivo pharmacodynamic activity of E5564 in normal volunteers with experimental endotoxemia [corrected].
The Journal of pharmacology and experimental therapeutics, , Volume: 308, Issue:1
2004
Antagonism of in vivo and ex vivo response to endotoxin by E5564, a synthetic lipid A analogue.
Journal of endotoxin research, , Volume: 8, Issue:6
2002
Disposition of a synthetic analogue of lipid A (E5564) in rats.
Xenobiotica; the fate of foreign compounds in biological systems, , Volume: 33, Issue:3
2003