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Eritoran

Eritoran structure

CAS No:
185955-34-4
Formula:
C66H126N2O19P2
Chemical Name:
Eritoran
Synonyms:
α-D-Glucopyranose,3-O-decyl-2-deoxy-6-O-[2-deoxy-3-O-[(3R)-3-methoxydecyl]-6-O-methyl-2-[[(11Z)-1-oxo-11-octadecen-1-yl]amino]-4-O-phosphono-β-D-glucopyranosyl]-2-[(1,3-dioxotetradecyl)amino]-,1-(dihydrogen phosphate);α-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-β-D-glucopyranosyl]-2-[(1,3-dioxotetradecyl)amino]-,1-(dihydrogen phosphate);Eritoran;261504-30-7
Categories:
Specialty Chemicals

Description

Eritoran is a lipid A derivative used for the treatment of severe sepsis. It is a conjugate acid of an eritoran(4-).|Eritoran is a structural analogue of the lipid A portion of lipopolysaccharide (LPS). It is being developed by Eisai Research Institute of Boston for the treatment of severe sepsis.|Eritoran is a synthetic analogue of the lipid A portion of the endotoxin lipopolysaccharide (LPS) with potential immunomodulating activity. Eritoran binds to a receptor complex composed of toll-like receptor 4 (TLR4), CD14 and MD2 (MD-2, LY96) that is present on most cells of the immune system, inhibiting the activation of the receptor complex by LPS, which may result in the inhibition of pro-inflammatory cytokine secretion and a potentially fatal systemic inflammatory response syndrome (SIRS). LPS is found in the outer membrane of Gram-negative bacteria and binds to the TLR4/CD14/MD2 receptor complex of immune cells, including macrophages, resulting in the release of pro-inflammatory cytokines.

Eritoran Basic Attributes

Molecular Weight：

1401.59

Exact Mass：

1313.66

UNII：

551541VI0Y

NCI Thesaurus Code：

C80053

Characteristics

PSA：

324.57000

XLogP3：

16.14580

Density：

1.14

Toxicity

Protein Binding：

Approximately 55%, primarily to high-density lipoproteins.

Drug Information

Drug Indication：

Investigated for use/treatment in sepsis and septicemia.|Sepsis

Pharmacology：

Eritoran has been shown to down-regulate the intracellular generation of pro-inflammatory cytokines IL-6 and TNF-alpha in human monocytes.

Biological Half-Life：

50.4 to 62.7 hours

Mechanism of Action：

Eritoran is a toll-like receptor 4 inhibitor.

MeSH Entry Terms：

3-O-decyl-2-deoxy-6-O-(2-deoxy-3-O-(3-methoxydecyl)-6-O-methyl-2-((1-oxo-11-octadecenyl)amino)-4-O-phosphonoglucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-1-(dihydroxy phosphate)glucopyranose

Eritoran Use and Manufacturing

Uses

Treatment of sepsis and other diseases due to reaction to bacterial endotoxin (endotoxin antagonist).

Use Classification：

Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:1313.7
XLogP3:15.4
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:19
Rotatable Bond Count:59
Exact Mass:1312.84300379
Monoisotopic Mass:1312.84300379
Topological Polar Surface Area:294
Heavy Atom Count:89
Complexity:1900
Defined Atom Stereocenter Count:11
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Eritoran

Xi'an Lanshan Biotechnology Co., Ltd. Contact Supplier

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CAS No.: 185955-34-4

Grade: Pharmaceutical Grade

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CAS No.: 185955-34-4

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