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MedKoo Cat#: 414065 | Name: Eritoran free acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eritoran Free Base is an investigational drug for the treatment of severe sepsis, an excessive inflammatory response to an infection. In a phase III clinical trial, eritoran did not perform better than placebo for the treatment of sepsis.

Chemical Structure

Eritoran free acid
Eritoran free acid
CAS#185955-34-4 (free base)

Theoretical Analysis

MedKoo Cat#: 414065

Name: Eritoran free acid

CAS#: 185955-34-4 (free base)

Chemical Formula: C66H126N2O19P2

Exact Mass: 1312.8430

Molecular Weight: 1313.68

Elemental Analysis: C, 60.34; H, 9.67; N, 2.13; O, 23.14; P, 4.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
185955-34-4 (free base) 185954-98-7 (tetrasodium)
Synonym
Eritoran free acid; B-1287; B1287; B 1287; E 5564; E-5564; E5564;
IUPAC/Chemical Name
(2R,3R,4R,5S,6R)-4-(decyloxy)-5-hydroxy-6-((((2R,3R,4R,5S,6R)-4-(((R)-3-methoxydecyl)oxy)-6-(methoxymethyl)-3-((Z)-octadec-11-enamido)-5-(phosphonooxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3-(3-oxotetradecanamido)tetrahydro-2H-pyran-2-yl dihydrogen phosphate
InChi Key
BPSMYQFMCXXNPC-MFCPCZTFSA-N
InChi Code
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
SMILES Code
CCCCCCCCCCCC(CC(N[C@H]1[C@H](O[C@@H]([C@H]([C@@H]1OCCCCCCCCCC)O)CO[C@@H]2O[C@@H]([C@H]([C@@H]([C@H]2NC(CCCCCCCCC/C=C\CCCCCC)=O)OCC[C@H](OC)CCCCCCC)OP(O)(O)=O)COC)OP(O)(O)=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,313.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Shirey KA, Lai W, Scott AJ, Lipsky M, Mistry P, Pletneva LM, Karp CL, McAlees J, Gioannini TL, Weiss J, Chen WH, Ernst RK, Rossignol DP, Gusovsky F, Blanco JC, Vogel SN. The TLR4 antagonist Eritoran protects mice from lethal influenza infection. Nature. 2013 May 23;497(7450):498-502. doi: 10.1038/nature12118. Epub 2013 May 1. PMID: 23636320; PMCID: PMC3725830. 2: Opal SM, Laterre PF, Francois B, LaRosa SP, Angus DC, Mira JP, Wittebole X, Dugernier T, Perrotin D, Tidswell M, Jauregui L, Krell K, Pachl J, Takahashi T, Peckelsen C, Cordasco E, Chang CS, Oeyen S, Aikawa N, Maruyama T, Schein R, Kalil AC, Van Nuffelen M, Lynn M, Rossignol DP, Gogate J, Roberts MB, Wheeler JL, Vincent JL; ACCESS Study Group. Effect of eritoran, an antagonist of MD2-TLR4, on mortality in patients with severe sepsis: the ACCESS randomized trial. JAMA. 2013 Mar 20;309(11):1154-62. doi: 10.1001/jama.2013.2194. PMID: 23512062. 3: 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. doi: 10.1016/j.cell.2007.08.002. PMID: 17803912. 4: Barochia A, Solomon S, Cui X, Natanson C, Eichacker PQ. Eritoran tetrasodium (E5564) treatment for sepsis: review of preclinical and clinical studies. Expert Opin Drug Metab Toxicol. 2011 Apr;7(4):479-94. doi: 10.1517/17425255.2011.558190. Epub 2011 Feb 17. PMID: 21323610; PMCID: PMC3065179. 5: Younan P, Ramanathan P, Graber J, Gusovsky F, Bukreyev A. The Toll-Like Receptor 4 Antagonist Eritoran Protects Mice from Lethal Filovirus Challenge. mBio. 2017 Apr 25;8(2):e00226-17. doi: 10.1128/mBio.00226-17. PMID: 28442605; PMCID: PMC5405229. 6: Beigel JH, Nam HH, Adams PL, Krafft A, Ince WL, El-Kamary SS, Sims AC. Advances in respiratory virus therapeutics - A meeting report from the 6th isirv Antiviral Group conference. Antiviral Res. 2019 Jul;167:45-67. doi: 10.1016/j.antiviral.2019.04.006. Epub 2019 Apr 8. PMID: 30974127; PMCID: PMC7132446. 7: Kuo WT, Lee TC, Yu LC. Eritoran Suppresses Colon Cancer by Altering a Functional Balance in Toll-like Receptors That Bind Lipopolysaccharide. Cancer Res. 2016 Aug 15;76(16):4684-95. doi: 10.1158/0008-5472.CAN-16-0172. Epub 2016 Jun 21. PMID: 27328732. 8: Korff S, Loughran P, Cai C, Lee YS, Scott M, Billiar TR. Eritoran attenuates tissue damage and inflammation in hemorrhagic shock/trauma. J Surg Res. 2013 Oct;184(2):e17-25. doi: 10.1016/j.jss.2013.03.023. Epub 2013 Mar 27. PMID: 23777984. 9: Tidswell M, LaRosa SP. Toll-like receptor-4 antagonist eritoran tetrasodium for severe sepsis. Expert Rev Anti Infect Ther. 2011 May;9(5):507-20. doi: 10.1586/eri.11.27. PMID: 21609262. 10: Nau R, Djukic M, Spreer A, Ribes S, Eiffert H. Bacterial meningitis: an update of new treatment options. Expert Rev Anti Infect Ther. 2015;13(11):1401-23. doi: 10.1586/14787210.2015.1077700. Epub 2015 Aug 18. PMID: 26293166.

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