Page last updated: 2024-12-11

b 1287

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Description

E5564: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

eritoran tetrasodium : An organic sodium salt which is the tetrasodium salt of eritoran. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

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

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Except for the occurrence of phlebitis, eritoran administration over 72 h was safe and well tolerated."( Safety, pharmacokinetics, pharmacodynamics, and plasma lipoprotein distribution of eritoran (E5564) during continuous intravenous infusion into healthy volunteers.
Choo, E; Lynn, M; Moran, J; Rose, J; Rossignol, DP; Wasan, KM; Wong, N; Yau, E, 2004
)
0.32

Pharmacokinetics

ExcerptReferenceRelevance
"5 mg) have a long pharmacokinetic half-life, but a surprisingly short ex vivo and in vivo pharmacodynamic half-life (generally less than several hours)."( Extended in vivo pharmacodynamic activity of E5564 in normal volunteers with experimental endotoxemia [corrected].
D'Angelo, T; Gotzkowsky, S; Kao, RJ; Lynn, M; McMahon, FG; Noveck, R; Perdomo, CA; Rossignol, DP; Vargas, R; Wasan, KM; Wheeler, JL; Wong, YN, 2004
)
0.32
", Cmax (0-12),tmax (0-12),CL,t1/2, Vss, AUC(0-12), AUC(0-last), AUC(0-infinity), C(ss,min), C(ss,max), and C(ss,av)) exhibited any difference between these two groups."( Pharmacokinetics of E5564, a lipopolysaccharide antagonist, in patients with impaired hepatic function.
Allen, I; DiLea, C; Kao, R; Liang, E; Marino, M; Wong, YN, 2003
)
0.32
" Previous studies have shown that low doses (350 to 3,500 microg) of eritoran have demonstrated a long pharmacokinetic half-life but a short pharmacodynamic half-life."( Safety, pharmacokinetics, pharmacodynamics, and plasma lipoprotein distribution of eritoran (E5564) during continuous intravenous infusion into healthy volunteers.
Choo, E; Lynn, M; Moran, J; Rose, J; Rossignol, DP; Wasan, KM; Wong, N; Yau, E, 2004
)
0.32
" Eritoran tetrasodium quantitatively blocks LPS response in vivo in animal and human endotoxemia models and demonstrates a long pharmacokinetic half-life, but a short pharmacodynamic half-life."( Continuous pharmacodynamic activity of eritoran tetrasodium, a TLR4 antagonist, during intermittent intravenous infusion into normal volunteers.
Lynn, M; Noveck, R; Rossignol, DP; Wong, N, 2008
)
0.35
" Pharmacodynamic activity measured by an ex vivo LPS challenge assay, demonstrated dose-dependence for both E5564 and LPS and plasma levels of approximately 3 microg/ml E5564 or greater blocked up to 1 ng/ml LPS."( Continuous pharmacodynamic activity of eritoran tetrasodium, a TLR4 antagonist, during intermittent intravenous infusion into normal volunteers.
Lynn, M; Noveck, R; Rossignol, DP; Wong, N, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
"5 mg of E5564/h x 72 h completely blocked effects of endotoxin challenge at the end of dosing (72 h), and at 48 and 72 h postdosing."( Extended in vivo pharmacodynamic activity of E5564 in normal volunteers with experimental endotoxemia [corrected].
D'Angelo, T; Gotzkowsky, S; Kao, RJ; Lynn, M; McMahon, FG; Noveck, R; Perdomo, CA; Rossignol, DP; Vargas, R; Wasan, KM; Wheeler, JL; Wong, YN, 2004
)
0.32
" Repeated dosing with 50 microg of E5564 intratracheally did not cause any measurable toxicity."( Toll-like receptor 4 antagonist (E5564) prevents the chronic airway response to inhaled lipopolysaccharide.
Brass, DM; Lawson, BL; McElvania-Tekippe, E; Savov, JD; Schwartz, DA; Walker, JK, 2005
)
0.33
"We tested whether clinically relevant variables, including the timing of treatment and the route of infection, influenced the effective dosing of E5564 in Escherichia coli-challenged rats."( Effective dosing of lipid A analogue E5564 in rats depends on the timing of treatment and the route of Escherichia coli infection.
Banks, SM; Cui, X; Danner, RL; Eichacker, PQ; Fitz, Y; Gerstenberger, E; Natanson, C; Solomon, SB, 2006
)
0.33
"These findings suggest that, for maximal clinical benefit, E5564 should be given early and that dosing should be adjusted upward for intravascular infection and downward for extravascular infection."( Effective dosing of lipid A analogue E5564 in rats depends on the timing of treatment and the route of Escherichia coli infection.
Banks, SM; Cui, X; Danner, RL; Eichacker, PQ; Fitz, Y; Gerstenberger, E; Natanson, C; Solomon, SB, 2006
)
0.33
"Every 12-h dosing of E5564 can replace continuous infusion, while maintaining uninterrupted blocking of high-dose LPS."( Continuous pharmacodynamic activity of eritoran tetrasodium, a TLR4 antagonist, during intermittent intravenous infusion into normal volunteers.
Lynn, M; Noveck, R; Rossignol, DP; Wong, N, 2008
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
organic sodium salt
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

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
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.72

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.72 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index5.54 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.72)

All Compounds (24.57)

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%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]