ERITORAN TETRASODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C66H122N2O19P2.4Na
Molecular Weight	1401.5835
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].[Na+].[Na+].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=FEMINZOAAWPBPP-RHMAUSBNSA-J

InChI=1S/C66H126N2O19P2.4Na/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);;;;/q;4*+1/p-4/b26-25-;;;;/t54-,55-,56-,59-,60-,61-,62-,63-,64-,65-,66-;;;;/m1..../s1

HIDE SMILES / InChI

Molecular Formula	C66H122N2O19P2
Molecular Weight	1309.6244
Charge	-4
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	1
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:07:02 GMT 2023` Edited by `admin` on `Fri Dec 15 16:07:02 GMT 2023`
Record UNII	FUO195TC7O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERITORAN TETRASODIUM

Official Name

English

ERITORAN TETRASODIUM [USAN]

Common Name

English

E5564

Code

English

Eritoran tetrasodium [WHO-DD]

Common Name

English

B-1287

Code

English

ERITORAN TETRASODIUM SALT

Common 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-PHOSPHONATO-.BETA.-D-GLUCOPYRANOSYL)-2-((3-OXOTETRADECANOYL)AMINO)-.ALPHA.-D-GLUCOPYRANOSYL TETRASODIUM PHOSPHATE

Common Name

English

ERITORAN TETRASODIUM SALT [MI]

Common Name

English

ERITORAN SODIUM [JAN]

Common Name

English

B1287

Code

English

E-5564

Code

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), TETRASODIUM SALT

Common Name

English

ERITORAN SODIUM

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308