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MedKoo Cat#: 529005 | Name: Eritoran Tetrasodium

Description:

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

Eritoran Tetrasodium is a TLR4 receptor antagonist potentially for the treatment of type 2 diabetes.

Chemical Structure

Eritoran Tetrasodium
Eritoran Tetrasodium
CAS#185954-98-7 (tetrasodium)

Theoretical Analysis

MedKoo Cat#: 529005

Name: Eritoran Tetrasodium

CAS#: 185954-98-7 (tetrasodium)

Chemical Formula: C66H122N2Na4O19P2

Exact Mass:

Molecular Weight: 1401.60

Elemental Analysis: C, 56.56; H, 8.77; N, 2.00; Na, 6.56; O, 21.69; P, 4.42

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
B-1287; B1287; B 1287; E 5564; E-5564; E5564; Eritoran Tetrasodium
IUPAC/Chemical Name
Tetrasodium [(2R,3R,4R,5S,6R)-4-decoxy-5-hydroxy-6-[[(2R,3R,4R,5S,6R)-4-[(3R)-3-methoxydecoxy]-6-(methoxymethyl)-3-[[(Z)-octadec-11-enoyl]amino]-5-phosphonatooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] phosphate
InChi Key
FEMINZOAAWPBPP-RHMAUSBNSA-J
InChi Code
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/t53-,54-,55-,58-,59-,60-,61-,62-,63-,64-,65-;;/m1../s1
SMILES Code
O=P([O-])([O-])O[C@H]1O[C@H](CO[C@@H]2O[C@H](COC)[C@@H](OP([O-])([O-])=O)[C@H](OCC[C@H](OC)CCCCCCC)[C@H]2NC(CCCCCCCCC/C=C\CCCCCC)=O)[C@@H](O)[C@H](OCCCCCCCCCC)[C@H]1NC(CC(CCCCCCCCCCC)=O)=O.[Na+].[Na+].[Na+].[Na+]
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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 1,401.60 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: Mcdonald KA, Huang H, Tohme S, Loughran P, Ferrero K, Billiar T, Tsung A. Toll-like receptor 4 (TLR4) antagonist eritoran tetrasodium attenuates liver ischemia and reperfusion injury through inhibition of high-mobility group box protein B1 (HMGB1) signaling. Mol Med. 2015 Mar 13;20:639-48. doi: 10.2119/molmed.2014.00076. PubMed PMID: 25375408; PubMed Central PMCID: PMC4365061. 2: 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. PubMed PMID: 27328732. 3: 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. PubMed PMID: 23777984. 4: 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. PubMed PMID: 23512062. 5: Ekici F, Karaca EE, Korkmaz S, Yüksel O, Gülbahar Ö, Alper M, Ercan S, Or M. Effect of the Toll-like receptor 4 antagonist eritoran on retinochoroidal inflammatory damage in a rat model of endotoxin-induced inflammation. Mediators Inflamm. 2014;2014:643525. doi: 10.1155/2014/643525. PubMed PMID: 25165412; PubMed Central PMCID: PMC4084615. 6: Kalil AC, LaRosa SP, Gogate J, Lynn M, Opal SM; Eritoran Sepsis Study Group.. Influence of severity of illness on the effects of eritoran tetrasodium (E5564) and on other therapies for severe sepsis. Shock. 2011 Oct;36(4):327-31. doi: 10.1097/SHK.0b013e318227980e. PubMed PMID: 21701421. 7: Yeh YC, Ko WJ, Chan KC, Fan SZ, Tsai JC, Cheng YJ, Sun WZ. Effects of eritoran tetrasodium, a toll-like receptor 4 antagonist, on intestinal microcirculation in endotoxemic rats. Shock. 2012 May;37(5):556-61. doi: 10.1097/SHK.0b013e31824e20ef. PubMed PMID: 22392144. 8: Deguchi A, Tomita T, Ohto U, Takemura K, Kitao A, Akashi-Takamura S, Miyake K, Maru Y. Eritoran inhibits S100A8-mediated TLR4/MD-2 activation and tumor growth by changing the immune microenvironment. Oncogene. 2016 Mar 17;35(11):1445-56. doi: 10.1038/onc.2015.211. PubMed PMID: 26165843. 9: Fleischer JG, Rossignol D, Francis GA, Chan T, Lynn M, Wasan KM. Deactivation of the lipopolysaccharide antagonist eritoran (E5564) by high-density lipoprotein-associated apolipoproteins. Innate Immun. 2012 Feb;18(1):171-8. doi: 10.1177/1753425910394395. PubMed PMID: 21382909. 10: Ehrentraut H, Weber C, Ehrentraut S, Schwederski M, Boehm O, Knuefermann P, Meyer R, Baumgarten G. The toll-like receptor 4-antagonist eritoran reduces murine cardiac hypertrophy. Eur J Heart Fail. 2011 Jun;13(6):602-10. doi: 10.1093/eurjhf/hfr035. PubMed PMID: 21613426. 11: 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. Review. PubMed PMID: 21323610; PubMed Central PMCID: PMC3065179. 12: Liu M, Gu M, Xu D, Lv Q, Zhang W, Wu Y. Protective effects of Toll-like receptor 4 inhibitor eritoran on renal ischemia-reperfusion injury. Transplant Proc. 2010 Jun;42(5):1539-44. doi: 10.1016/j.transproceed.2010.03.133. PubMed PMID: 20620471. 13: 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. PubMed PMID: 23636320; PubMed Central PMCID: PMC3725830. 14: Aikawa N, Okubo Y, Lynn M, Rossignol DP, Wong YN, Schuck E, Kitahara Y, Nakano T, Sivak O, Wasan KM, Nagy C, Yen M. Safety, pharmacokinetics and pharmacodynamics of four-hour intravenous infusions of eritoran in healthy Japanese and Caucasian men. Innate Immun. 2012 Dec;18(6):793-803. doi: 10.1177/1753425912441845. PubMed PMID: 22459966. 15: Sun Y, Pearlman E. Inhibition of corneal inflammation by the TLR4 antagonist Eritoran tetrasodium (E5564). Invest Ophthalmol Vis Sci. 2009 Mar;50(3):1247-54. doi: 10.1167/iovs.08-2628. PubMed PMID: 18936141; PubMed Central PMCID: PMC3909488. 16: Tidswell M, Tillis W, Larosa SP, Lynn M, Wittek AE, Kao R, Wheeler J, Gogate J, Opal SM; Eritoran Sepsis Study Group.. Phase 2 trial of eritoran tetrasodium (E5564), a toll-like receptor 4 antagonist, in patients with severe sepsis. Crit Care Med. 2010 Jan;38(1):72-83. doi: 10.1097/CCM.0b013e3181b07b78. Erratum in: Crit Care Med. 2010 Sep;38(9):1925-6. Multiple investigator names added.. PubMed PMID: 19661804. 17: Wasan KM, Risovic V, Sivak O, Lee SD, Mason DX, Chiklis GR, McShane J, Lynn M, Wong N, Rossignol DP. Influence of plasma cholesterol and triglyceride concentrations and eritoran (E5564) micelle size on its plasma pharmacokinetics and ex vivo activity following single intravenous bolus dose into healthy female rabbits. Pharm Res. 2008 Jan;25(1):176-82. PubMed PMID: 17849177. 18: Raja SG, Dreyfus GD. Eritoran: the evidence of its therapeutic potential in sepsis. Core Evid. 2008 Feb 29;2(3):199-207. PubMed PMID: 21221186; PubMed Central PMCID: PMC3012437. 19: 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. Review. PubMed PMID: 21609262. 20: 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. PubMed PMID: 16820585.