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    Eritoran

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 185955-34-4, Eritoran [inn], E5564, Chembl501259, Chebi:68609, 551541vi0y
    Molecular Formula
    C66H126N2O19P2
    Molecular Weight
    1313.7  g/mol
    InChI Key
    BPSMYQFMCXXNPC-MFCPCZTFSA-N
    FDA UNII
    551541VI0Y
    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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(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-phosphonooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] dihydrogen phosphate
    2.1.2 InChI
    InChI=1S/C66H126N2O19P2/c1-7-11-15-19-22-25-26-27-28-29-30-32-34-38-42-46-57(70)67-60-64(82-49-47-54(80-6)45-41-36-18-14-10-4)62(86-88(73,74)75)56(51-79-5)85-65(60)83-52-55-61(72)63(81-48-43-39-35-24-21-17-13-9-3)59(66(84-55)87-89(76,77)78)68-58(71)50-53(69)44-40-37-33-31-23-20-16-12-8-2/h25-26,54-56,59-66,72H,7-24,27-52H2,1-6H3,(H,67,70)(H,68,71)(H2,73,74,75)(H2,76,77,78)/b26-25-/t54-,55-,56-,59-,60-,61-,62-,63-,64-,65-,66-/m1/s1
    2.1.3 InChI Key
    BPSMYQFMCXXNPC-MFCPCZTFSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCCC(=O)CC(=O)NC1C(C(C(OC1OP(=O)(O)O)COC2C(C(C(C(O2)COC)OP(=O)(O)O)OCCC(CCCCCCC)OC)NC(=O)CCCCCCCCCC=CCCCCCC)O)OCCCCCCCCCC
    2.1.5 Isomeric SMILES
    CCCCCCCCCCCC(=O)CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)O)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC)OP(=O)(O)O)OCC[C@@H](CCCCCCC)OC)NC(=O)CCCCCCCCC/C=C\CCCCCC)O)OCCCCCCCCCC
    2.2 Other Identifiers
    2.2.1 UNII
    551541VI0Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 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

    2.3.2 Depositor-Supplied Synonyms

    1. 185955-34-4

    2. Eritoran [inn]

    3. E5564

    4. Chembl501259

    5. Chebi:68609

    6. 551541vi0y

    7. [(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-phosphonooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] Dihydrogen Phosphate

    8. 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]-alpha-d-glucopyranose1-(dihydrogenphosphat

    9. 3-o-decyl-2-deoxy-6-o-{2-deoxy-3-o-[(3r)-3-methoxydecyl]-6-o-methyl-2-[(11e)-octadec-11-enoylamino]-4-o-phosphonato-beta-d-glucopyranosyl}-2-[(3-oxotetradecanoyl)amino]-1-o-phosphono-alpha-d-glucopyranose

    10. 3-o-decyl-2-deoxy-6-o-{2-deoxy-3-o-[(3r)-3-methoxydecyl]-6-o-methyl-2-[(11z)-octadec-11-enoylamino]-4-o-phosphono-beta-d-glucopyranosyl}-2-[(3-oxotetradecanoyl)amino]-1-o-phosphono-alpha-d-glucopyranose

    11. B1287

    12. Unii-551541vi0y

    13. Eritoran [mi]

    14. Eritoran [who-dd]

    15. E5564; Eritoran

    16. Gtpl4919

    17. Schembl10042156

    18. Dtxsid60873217

    19. Ex-a5458

    20. Bdbm50274760

    21. Db04933

    22. 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

    23. Q5389586

    24. .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)

    25. [(2r,3s,4r,5r,6r)-6-[[(2r,3s,4r,5r,6r)-4-decoxy-3-hydroxy-5-(3-oxotetradecanoylamino)-6-phosphonooxyoxan-2-yl]methoxy]-4-[(3r)-3-methoxydecoxy]-2-(methoxymethyl)-5-[[(z)-octadec-11-enoyl]amino]oxan-3-yl] Dihydrogen Phosphate

    26. 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-((3r)-3-methoxydecyl)-6-o-methyl-2-((11z)-octadec-11-enoylamino)-4-o-phosphono-.beta.-d-glucopyranosyl)-2-((3-oxotetradecanoyl)amino)-1-o-phosphono-.alpha.-d-glucopyranose

    2.4 Create Date
    2006-07-04
    3 Chemical and Physical Properties
    Molecular Weight 1313.7 g/mol
    Molecular Formula C66H126N2O19P2
    XLogP315.4
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count19
    Rotatable Bond Count59
    Exact Mass1312.84300379 g/mol
    Monoisotopic Mass1312.84300379 g/mol
    Topological Polar Surface Area294 Ų
    Heavy Atom Count89
    Formal Charge0
    Complexity1900
    Isotope Atom Count0
    Defined Atom Stereocenter Count11
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in sepsis and septicemia.

    Sepsis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

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

    5.2 Biological Half-Life

    50.4 to 62.7 hours

    5.3 Mechanism of Action

    Eritoran is a toll-like receptor 4 inhibitor.