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
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)
Research
Studies (39)
Timeframe | Studies, This Drug (%) | All Drugs % |
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 1 (2.56) | 18.2507 |
2000's | 23 (58.97) | 29.6817 |
2010's | 15 (38.46) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
Trials | 6 (15.38%) | 5.53% |
Reviews | 2 (5.13%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 31 (79.49%) | 84.16% |
Condition | Indicated | Studies | First Year | Last Year | Average Age | Relationship Strength | Trials | pre-1990 | 1990's | 2000's | 2010's | post-2020 |
Acute Hepatic Failure | 0 | | 2009 | 2010 | 14.5 | low | 0 | 0 | 0 | 2 | 0 | 0 |
Acute Lung Injury | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Acute Respiratory Distress Syndrome | 0 | | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Airflow Obstruction, Chronic | 0 | | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Airway Hyper-Responsiveness | 0 | | 2005 | 2005 | 19.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Asthma | 0 | | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Asthma, Bronchial | 0 | | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Bacterial Disease | 0 | | 2010 | 2010 | 14.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Bacterial Infections | 0 | | 2010 | 2010 | 14.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Bacterial Infections, Gram-Negative | 0 | | 2006 | 2006 | 18.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Blood Poisoning | 0 | | 2004 | 2014 | 15.7 | low | 2 | 0 | 0 | 5 | 1 | 0 |
Body Weight | 0 | | 2015 | 2015 | 9.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Brain Ischemia | 0 | | 2019 | 2019 | 5.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Cardiomyopathies | 0 | | 2006 | 2006 | 18.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Cardiomyopathies, Primary | 0 | | 2006 | 2006 | 18.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Cerebral Ischemia | 0 | | 2019 | 2019 | 5.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Cirrhosis, Liver | 0 | | 2003 | 2003 | 21.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Complication, Postoperative | 0 | | 2007 | 2007 | 17.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Critical Illness | 0 | | 2010 | 2010 | 14.0 | low | 2 | 0 | 0 | 2 | 0 | 0 |
Diabetes Mellitus | 0 | | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Disease Models, Animal | 0 | | 2002 | 2019 | 13.9 | low | 0 | 0 | 0 | 5 | 3 | 0 |
E coli Infections | 0 | | 2006 | 2014 | 14.0 | low | 0 | 0 | 0 | 1 | 1 | 0 |
Endotoxemia | 0 | | 2003 | 2008 | 19.0 | low | 2 | 0 | 0 | 5 | 0 | 0 |
Endotoxin Shock | 0 | | 2003 | 2004 | 20.5 | low | 0 | 0 | 0 | 2 | 0 | 0 |
Enterocolitis, Necrotizing | 0 | | 2013 | 2013 | 11.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Escherichia coli Infections | 0 | | 2006 | 2014 | 14.0 | low | 0 | 0 | 0 | 1 | 1 | 0 |
Experimental Lung Inflammation | 0 | | 2005 | 2005 | 19.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Gram-Negative Bacterial Infections | 0 | | 2006 | 2006 | 18.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Grippe | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Hemorrhagic Shock | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Infections, Orthomyxoviridae | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Infections, Pseudomonas | 0 | | 2013 | 2013 | 11.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Infections, Respiratory Syncytial Virus | 0 | | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Inflammation | 0 | | 2001 | 2018 | 12.8 | low | 0 | 0 | 0 | 1 | 3 | 0 |
Influenza, Human | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Injuries, Soft Tissue | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Injury, Ischemia-Reperfusion | 0 | | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Innate Inflammatory Response | 0 | | 2001 | 2018 | 12.8 | low | 0 | 0 | 0 | 1 | 3 | 0 |
Insulin Resistance | 0 | | 2015 | 2015 | 9.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Insulin Sensitivity | 0 | | 2015 | 2015 | 9.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Ischemia | 0 | | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Liver Cirrhosis | 0 | | 2003 | 2003 | 21.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Liver Failure, Acute | 0 | | 2009 | 2010 | 14.5 | low | 0 | 0 | 0 | 2 | 0 | 0 |
Lung Injury, Acute | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Necrotizing Enterocolitis | 0 | | 2013 | 2013 | 11.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Obesity | 0 | | 2015 | 2015 | 9.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Orthomyxoviridae Infections | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Periphlebitis | 0 | | 2008 | 2008 | 16.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Peritonitis | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Phlebitis | 0 | | 2008 | 2008 | 16.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Pneumonia | 0 | | 2005 | 2005 | 19.0 | low | 0 | 0 | 0 | 1 | 0 | 0 |
Postoperative Complications | 0 | | 2007 | 2007 | 17.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Primary Peritonitis | 0 | | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Pseudomonas Infections | 0 | | 2013 | 2013 | 11.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Pulmonary Disease, Chronic Obstructive | 0 | | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Reperfusion Injury | 0 | | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Respiratory Distress Syndrome | 0 | | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Respiratory Syncytial Virus Infections | 0 | | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Sensitivity and Specificity | 0 | | 1999 | 1999 | 25.0 | low | 0 | 0 | 1 | 0 | 0 | 0 |
Sepsis | 1 | | 2004 | 2014 | 15.7 | low | 2 | 0 | 0 | 5 | 1 | 0 |
Shock, Septic | 0 | | 2003 | 2004 | 20.5 | low | 0 | 0 | 0 | 2 | 0 | 0 |
Tachyarrhythmia | 0 | | 2004 | 2004 | 20.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Tachycardia | 0 | | 2004 | 2004 | 20.0 | low | 1 | 0 | 0 | 1 | 0 | 0 |
Ex-vivo generation of drug-eluting islets improves transplant outcomes by inhibiting TLR4-Mediated NFkB upregulation.Biomaterials, , Volume: 159, 2018
Pseudomonas aeruginosa outer membrane vesicles modulate host immune responses by targeting the Toll-like receptor 4 signaling pathway.Infection and immunity, , Volume: 81, Issue:12, 2013
Discovery and validation of a new class of small molecule Toll-like receptor 4 (TLR4) inhibitors.PloS one, , Volume: 8, Issue:6, 2013
The extra domain A of fibronectin activates Toll-like receptor 4.The Journal of biological chemistry, , Mar-30, Volume: 276, Issue:13, 2001
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
Risk of death and the efficacy of eritoran tetrasodium (E5564): design considerations for clinical trials of anti-inflammatory agents in sepsis.Critical care medicine, , Volume: 38, Issue:1, 2010
Phase 2 trial of eritoran tetrasodium (E5564), a toll-like receptor 4 antagonist, in patients with severe sepsis.Critical care medicine, , Volume: 38, Issue:1, 2010
Syntheses of glucose analogues of E5564 as a highly potent anti-sepsis drug candidate.Bioorganic & medicinal chemistry, , May-01, Volume: 14, Issue:9, 2006
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
Drug evaluation: E-5564.IDrugs : the investigational drugs journal, , Volume: 7, Issue:6, 2004
Continuous pharmacodynamic activity of eritoran tetrasodium, a TLR4 antagonist, during intermittent intravenous infusion into normal volunteers.Innate immunity, , Volume: 14, Issue:6, 2008
Toll-like receptor 4, nitric oxide, and myocardial depression in endotoxemia.Shock (Augusta, Ga.), , Volume: 25, Issue:1, 2006
Drug evaluation: E-5564.IDrugs : the investigational drugs journal, , Volume: 7, Issue:6, 2004
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
Blocking of responses to endotoxin by E5564 in healthy volunteers with experimental endotoxemia.The Journal of infectious diseases, , Feb-15, Volume: 187, Issue:4, 2003
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
Risk of death and the efficacy of eritoran tetrasodium (E5564): design considerations for clinical trials of anti-inflammatory agents in sepsis.Critical care medicine, , Volume: 38, Issue:1, 2010
Phase 2 trial of eritoran tetrasodium (E5564), a toll-like receptor 4 antagonist, in patients with severe sepsis.Critical care medicine, , Volume: 38, Issue:1, 2010
Syntheses of glucose analogues of E5564 as a highly potent anti-sepsis drug candidate.Bioorganic & medicinal chemistry, , May-01, Volume: 14, Issue:9, 2006
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
Drug evaluation: E-5564.IDrugs : the investigational drugs journal, , Volume: 7, Issue:6, 2004
Early toll-like receptor 4 blockade reduces ROS and inflammation triggered by microglial pro-inflammatory phenotype in rodent and human brain ischaemia models.British journal of pharmacology, , Volume: 176, Issue:15, 2019
Insights into endotoxin-mediated lung inflammation and future treatment strategies.Expert review of respiratory medicine, , Volume: 12, Issue:11, 2018
N-acetyl-l-cystine (NAC) protects against H9N2 swine influenza virus-induced acute lung injury.International immunopharmacology, , Volume: 22, Issue:1, 2014
Salvage effect of E5564, Toll-like receptor 4 antagonist on d-galactosamine and lipopolysaccharide-induced acute liver failure in rats.Journal of gastroenterology and hepatology, , Volume: 25, Issue:5, 2010
Therapeutic approach to regulate innate immune response by Toll-like receptor 4 antagonist E5564 in rats with D-galactosamine-induced acute severe liver injury.Journal of gastroenterology and hepatology, , Volume: 24, Issue:6, 2009
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
Inhibition of endotoxin response by e5564, a novel Toll-like receptor 4-directed endotoxin antagonist.The Journal of pharmacology and experimental therapeutics, , Volume: 304, Issue:3, 2003
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
Ex-vivo generation of drug-eluting islets improves transplant outcomes by inhibiting TLR4-Mediated NFkB upregulation.Biomaterials, , Volume: 159, 2018
Discovery and validation of a new class of small molecule Toll-like receptor 4 (TLR4) inhibitors.PloS one, , Volume: 8, Issue:6, 2013
Pseudomonas aeruginosa outer membrane vesicles modulate host immune responses by targeting the Toll-like receptor 4 signaling pathway.Infection and immunity, , Volume: 81, Issue:12, 2013
The extra domain A of fibronectin activates Toll-like receptor 4.The Journal of biological chemistry, , Mar-30, Volume: 276, Issue:13, 2001
Phase 2 trial of eritoran tetrasodium (E5564), a toll-like receptor 4 antagonist, in patients with severe sepsis.Critical care medicine, , Volume: 38, Issue:1, 2010
Risk of death and the efficacy of eritoran tetrasodium (E5564): design considerations for clinical trials of anti-inflammatory agents in sepsis.Critical care medicine, , Volume: 38, Issue:1, 2010
Safety/Toxicity (1)
Pharmacokinetics (6)
Article | Year |
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)
Article | Year |
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 |