U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ERITORAN TETRASODIUM

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

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

Curator's Comment: Eritoran is CNS active in animals. No human data available.

Approval Year

PubMed

PubMed

TitleDatePubMed
CD11/CD18 and CD14 share a common lipid A signaling pathway.
1998 Nov 15
Involvement of oxidative stress and immune- and inflammation-related factors in azathioprine-induced liver injury.
2014 Jan 13
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

Sample Use Guides

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 UTC 2023
Edited
by admin
on Fri Dec 15 16:07:02 UTC 2023
Record UNII
FUO195TC7O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERITORAN TETRASODIUM
USAN   WHO-DD  
USAN  
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
MI  
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
JAN  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C308
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
Code System Code Type Description
MERCK INDEX
m4999
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY Merck Index
PUBCHEM
6450173
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
FDA UNII
FUO195TC7O
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL501259
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
CAS
185954-98-7
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
NCI_THESAURUS
C91759
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
SMS_ID
100000175500
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
DRUG BANK
DBSALT001799
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
CAS
1029325-41-4
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
NON-SPECIFIC STOICHIOMETRY
CHEBI
46692
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
USAN
QQ-07
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
MESH
C404742
Created by admin on Fri Dec 15 16:07:02 UTC 2023 , Edited by admin on Fri Dec 15 16:07:02 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY