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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29561292
Curator's Comment: Eritoran is CNS active in animals. No human data available.
Originator
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19661804
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
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NCI_THESAURUS |
C308
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m4999
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6450173
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FUO195TC7O
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185954-98-7
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C91759
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1029325-41-4
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C404742
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ACTIVE MOIETY
SUBSTANCE RECORD