Eritoran

Title: Eritoran
CAS Registry Number: 185955-34-4
CAS Name: 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-b-D-glucopyranosyl]-2-[(1,3-dioxotetradecyl)amino]-a-D-glucopyranose 1-(dihydrogen phosphate)
Molecular Formula: C66H126N2O19P2
Molecular Weight: 1313.66
Percent Composition: C 60.34%, H 9.67%, N 2.13%, O 23.14%, P 4.72%
Literature References: Toll-like receptor 4 (TLR4) antagonist. Synthetic analog of the lipid A component of endotoxin, a major constituent of the outer membrane of Gram negative bacteria. Prepn: W. J. Christ et al., WO 9639411; eidem, US 5750664 (1996, 1998 both to Eisai). Pharmacology: M. Mullarkey et al., J. Pharmacol. Exp. Ther. 304, 1093 (2003). Clinical pharmacokinetics: Y. N. Wong et al., J. Clin. Pharmacol. 43, 735 (2003); and lipid distribution profile: D. P. Rossignol et al., Antimicrob. Agents Chemother. 48, 3233 (2004). Clinical evaluation in experimental endotoxemia: M. Lynn et al., J. Pharmacol. Exp. Ther. 308, 175 (2004). Review of pharmacology and clinical experience: D. P. Rossignol, M. Lynn, Curr. Opin. Invest. Drugs 6, 496-502 (2005).
Derivative Type: Tetrasodium salt
CAS Registry Number: 185954-98-7
Manufacturers' Codes: E-5564; B-1287
Molecular Formula: C66H122N2Na4O19P2
Molecular Weight: 1401.58
Percent Composition: C 56.56%, H 8.77%, N 2.00%, Na 6.56%, O 21.69%, P 4.42%
Therap-Cat: In treatment of severe sepsis.
Keywords: Antisepsis.
Erlotinib Ertapenem Erucic Acid Erythritol Erythritol Anhydride

Eritoran
Eritoran free acid skeletal.svg
Systematic (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-phosphonatooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] phosphoric acid
Clinical data
Legal status Investigational
Routes Intravenous injection
Identifiers
CAS number 185955-34-4 N
185954-98-7 (tetrasodium salt)
ATC code None
PubChem CID 6912404
UNII 551541VI0Y N
ChEMBL CHEMBL501259 N
Synonyms E 5564
Chemical data
Formula C66H126N2O19P2 
Mol. mass 1313.656 g/mol
 N (what is this?)  (verify)

Eritoran is an investigational drug for the treatment of severe sepsis, an excessive inflammatory response to an infection. It is being developed by the Japanese pharmaceutical company Eisai Co. and administered intravenously as the sodium salt eritoran tetrasodium.[1][2]

In a phase III clinical trial,[3] eritoran did not perform better than existing treatments for the treatment of sepsis.[4][5]