Identification
- Generic Name
- Eritoran
- DrugBank Accession Number
- DB04933
- Background
Eritoran is a structural analogue of the lipid A portion of lipopolysaccharide (LPS). It is being developed by Eisai Research Institute of Boston for the treatment of severe sepsis.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Eritoran (DB04933)
- Weight
- Average: 1313.6562
Monoisotopic: 1312.843002884 - Chemical Formula
- C66H126N2O19P2
- Synonyms
- Eritoran
- Eritorán
- Éritoran
- Eritoranum
- External IDs
- E5564
Pharmacology
- Indication
Investigated for use/treatment in sepsis and septicemia.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Eritoran has been shown to down-regulate the intracellular generation of pro-inflammatory cytokines IL-6 and TNF-alpha in human monocytes.
- Mechanism of action
Eritoran is a toll-like receptor 4 inhibitor.
Target Actions Organism UToll-like receptor 4 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Approximately 55%, primarily to high-density lipoproteins.
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
50.4 to 62.7 hours
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Eritoran tetrasodium FUO195TC7O 185954-98-7 FEMINZOAAWPBPP-RHMAUSBNSA-J
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Acylaminosugars
- Alternative Parents
- Hexose phosphates / Disaccharide phosphates / N-acyl-alpha-hexosamines / O-glycosyl compounds / Monoalkyl phosphates / N-acyl amines / 1,3-dicarbonyl compounds / Oxanes / Ketones / Secondary carboxylic acid amides show 8 more
- Substituents
- 1,3-dicarbonyl compound / Acetal / Acylaminosugar / Alcohol / Aliphatic heteromonocyclic compound / Alkyl phosphate / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkyl ether show 24 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- lipid As (CHEBI:68609)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 551541VI0Y
- CAS number
- 185955-34-4
- InChI Key
- BPSMYQFMCXXNPC-MFCPCZTFSA-N
- InChI
- 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
- IUPAC Name
- {[(2R,3R,4R,5S,6R)-4-(decyloxy)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-4-{[(3R)-3-methoxydecyl]oxy}-6-(methoxymethyl)-3-[(11Z)-octadec-11-enamido]-5-(phosphonooxy)oxan-2-yl]oxy}methyl)-3-(3-oxotetradecanamido)oxan-2-yl]oxy}phosphonic acid
- 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
References
- General References
- Rossignol DP, Wasan KM, Choo E, Yau E, Wong N, Rose J, Moran J, Lynn M: Safety, pharmacokinetics, pharmacodynamics, and plasma lipoprotein distribution of eritoran (E5564) during continuous intravenous infusion into healthy volunteers. Antimicrob Agents Chemother. 2004 Sep;48(9):3233-40. [Article]
- External Links
- PDB Entries
- 2z65 / 3ula
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Severe Sepsis 1 3 Recruiting Treatment Community-acquired Pneumonia, Influenza, COVID-19 / Coronavirus Disease 2019 (COVID‑19) 1 2 Completed Treatment Infection / Sepsis / Sepsis Syndromes / Septic Shock / Septicemia 1 2 Completed Treatment Insulin Sensitivity 1 2 Terminated Treatment Insulin Sensitivity 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00458 mg/mL ALOGPS logP 6.98 ALOGPS logP 15.5 Chemaxon logS -5.5 ALOGPS pKa (Strongest Acidic) 0.55 Chemaxon pKa (Strongest Basic) -3.6 Chemaxon Physiological Charge -4 Chemaxon Hydrogen Acceptor Count 17 Chemaxon Hydrogen Donor Count 7 Chemaxon Polar Surface Area 293.63 Å2 Chemaxon Rotatable Bond Count 59 Chemaxon Refractivity 346.56 m3·mol-1 Chemaxon Polarizability 152.32 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9874 Blood Brain Barrier - 0.9401 Caco-2 permeable - 0.6624 P-glycoprotein substrate Substrate 0.7565 P-glycoprotein inhibitor I Inhibitor 0.6447 P-glycoprotein inhibitor II Inhibitor 0.565 Renal organic cation transporter Non-inhibitor 0.9358 CYP450 2C9 substrate Non-substrate 0.752 CYP450 2D6 substrate Non-substrate 0.8462 CYP450 3A4 substrate Substrate 0.6583 CYP450 1A2 substrate Non-inhibitor 0.8413 CYP450 2C9 inhibitor Non-inhibitor 0.7925 CYP450 2D6 inhibitor Non-inhibitor 0.8903 CYP450 2C19 inhibitor Non-inhibitor 0.7586 CYP450 3A4 inhibitor Inhibitor 0.5831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9351 Ames test Non AMES toxic 0.6815 Carcinogenicity Non-carcinogens 0.9384 Biodegradation Not ready biodegradable 0.7395 Rat acute toxicity 2.7745 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8974 hERG inhibition (predictor II) Non-inhibitor 0.6143
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 371.8752 predictedDeepCCS 1.0 (2019) [M+H]+ 373.9392 predictedDeepCCS 1.0 (2019) [M+Na]+ 381.33432 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Cooperates with LY96 and CD14 to mediate the innate immune response to bacterial lipopolysaccharide (LPS). Acts via MYD88, TIRAP and TRAF6, leading to NF-kappa-B activation, cytokine secretion and ...
- Gene Name
- TLR4
- Uniprot ID
- O00206
- Uniprot Name
- Toll-like receptor 4
- Molecular Weight
- 95679.19 Da
References
- Kim HM, Park BS, Kim JI, Kim SE, Lee J, Oh SC, Enkhbayar P, Matsushima N, Lee H, Yoo OJ, Lee JO: Crystal structure of the TLR4-MD-2 complex with bound endotoxin antagonist Eritoran. Cell. 2007 Sep 7;130(5):906-17. [Article]
- Shimamoto A, Chong AJ, Yada M, Shomura S, Takayama H, Fleisig AJ, Agnew ML, Hampton CR, Rothnie CL, Spring DJ, Pohlman TH, Shimpo H, Verrier ED: Inhibition of Toll-like receptor 4 with eritoran attenuates myocardial ischemia-reperfusion injury. Circulation. 2006 Jul 4;114(1 Suppl):I270-4. [Article]
Drug created at October 21, 2007 22:23 / Updated at September 15, 2021 23:26