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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 of ERITORAN

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

Molecular Formula C66H126N2O19P2
Molecular Weight 1313.6562
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 1
Optical Activity UNSPECIFIED

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

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 Wed Jul 05 23:10:59 UTC 2023
Edited
by admin
on Wed Jul 05 23:10:59 UTC 2023
Record UNII
551541VI0Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERITORAN
INN   MI   WHO-DD  
INN  
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
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
Code System Code Type Description
DRUG BANK
DB04933
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
INN
8562
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
SMS_ID
100000146621
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
MESH
C512420
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
WIKIPEDIA
ERITORAN
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID60873217
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
CAS
185955-34-4
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
NCI_THESAURUS
C80053
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
FDA UNII
551541VI0Y
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL501259
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
DRUG CENTRAL
1044
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
PUBCHEM
6912404
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
MERCK INDEX
M4999
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY Merck Index
EVMPD
SUB125527
Created by admin on Wed Jul 05 23:10:59 UTC 2023 , Edited by admin on Wed Jul 05 23:10:59 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY