ERITORAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C66H126N2O19P2
Molecular Weight	1313.6562
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCC(=O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO[C@@H]2O[C@H](COC)[C@@H](OP(O)(O)=O)[C@H](OCC[C@@H](CCCCCCC)OC)[C@H]2NC(=O)CCCCCCCCC\C=C/CCCCCC)[C@@H](O)[C@@H]1OCCCCCCCCCC

InChI

InChIKey=BPSMYQFMCXXNPC-MFCPCZTFSA-N

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

HIDE SMILES / InChI

Description
Sources: https://adisinsight.springer.com/drugs/800012300 | https://www.ncbi.nlm.nih.gov/pubmed/15328078 | https://www.ncbi.nlm.nih.gov/pubmed/21323610

Eritoran (E-5564) is a synthetic lipid A analog that has been designed to antagonize the effects of lipopolysaccharide (LPS) and has been found to do this by interacting with Toll-like receptor 4, the cell surface receptor for LPS. Preclinical in vitro and in vivo studies of eritoran tetrasodium indicate it can limit excessive inflammatory mediator release associated with LPS and improve survival in sepsis models. Clinically, eritoran was being investigated for the treatment of severe sepsis, septic shock, and other endotoxin-mediated indications. Eritoran development has been discontinued.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
CD11/CD18 and CD14 share a common lipid A signaling pathway.	1998 Nov 15	9820516
Involvement of oxidative stress and immune- and inflammation-related factors in azathioprine-induced liver injury.	2014 Jan 13	24184165
Development of a cell-based assay system considering drug metabolism and immune- and inflammatory-related factors for the risk assessment of drug-induced liver injury.	2014 Jul 3	24747151

Sample Use Guides

In Vivo Use Guide

Phase 2 trial in patients with severe sepsis: intravenous eritoran tetrasodium (total dose of either 45 mg or 105 mg) or placebo administered every 12 hrs for 6 days.

Route of Administration: Intravenous

Name

Type

Language

ERITORAN

Official Name

English

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

Common Name

English

eritoran [INN]

Common Name

English

.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)

Common Name

English

ERITORAN [MI]

Common Name

English

Eritoran [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308