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Chemistry

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Also known as: 185955-34-4, Eritoran [inn], E5564, Chembl501259, Chebi:68609, 551541vi0y
Molecular Formula
C66H126N2O19P2
Molecular Weight
1313.7  g/mol
InChI Key
BPSMYQFMCXXNPC-MFCPCZTFSA-N
FDA UNII
551541VI0Y

Eritoran
Eritoran is a synthetic analogue of the lipid A portion of the endotoxin lipopolysaccharide (LPS) with potential immunomodulating activity. Eritoran binds to a receptor complex composed of toll-like receptor 4 (TLR4), CD14 and MD2 (MD-2, LY96) that is present on most cells of the immune system, inhibiting the activation of the receptor complex by LPS, which may result in the inhibition of pro-inflammatory cytokine secretion and a potentially fatal systemic inflammatory response syndrome (SIRS). LPS is found in the outer membrane of Gram-negative bacteria and binds to the TLR4/CD14/MD2 receptor complex of immune cells, including macrophages, resulting in the release of pro-inflammatory cytokines.
1 2D Structure

Eritoran

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(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-phosphonooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] dihydrogen phosphate
2.1.2 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
2.1.3 InChI Key
BPSMYQFMCXXNPC-MFCPCZTFSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCC(=O)CC(=O)NC1C(C(C(OC1OP(=O)(O)O)COC2C(C(C(C(O2)COC)OP(=O)(O)O)OCCC(CCCCCCC)OC)NC(=O)CCCCCCCCCC=CCCCCCC)O)OCCCCCCCCCC
2.1.5 Isomeric SMILES
CCCCCCCCCCCC(=O)CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)O)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC)OP(=O)(O)O)OCC[C@@H](CCCCCCC)OC)NC(=O)CCCCCCCCC/C=C\CCCCCC)O)OCCCCCCCCCC
2.2 Other Identifiers
2.2.1 UNII
551541VI0Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-(3-methoxydecyl)-6-o-methyl-2-((1-oxo-11-octadecenyl)amino)-4-o-phosphonoglucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-1-(dihydroxy Phosphate)glucopyranose

2.3.2 Depositor-Supplied Synonyms

1. 185955-34-4

2. Eritoran [inn]

3. E5564

4. Chembl501259

5. Chebi:68609

6. 551541vi0y

7. [(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-phosphonooxyoxan-2-yl]oxymethyl]-3-(3-oxotetradecanoylamino)oxan-2-yl] Dihydrogen Phosphate

8. 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]-alpha-d-glucopyranose1-(dihydrogenphosphat

9. 3-o-decyl-2-deoxy-6-o-{2-deoxy-3-o-[(3r)-3-methoxydecyl]-6-o-methyl-2-[(11e)-octadec-11-enoylamino]-4-o-phosphonato-beta-d-glucopyranosyl}-2-[(3-oxotetradecanoyl)amino]-1-o-phosphono-alpha-d-glucopyranose

10. 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

11. B1287

12. Unii-551541vi0y

13. Eritoran [mi]

14. Eritoran [who-dd]

15. E5564; Eritoran

16. Gtpl4919

17. Schembl10042156

18. Dtxsid60873217

19. Ex-a5458

20. Bdbm50274760

21. Db04933

22. 3-o-decyl-2-deoxy-6-o-(2-deoxy-3-o-(3-methoxydecyl)-6-o-methyl-2-((1-oxo-11-octadecenyl)amino)-4-o-phosphonoglucopyranosyl)-2-((1,3-dioxotetradecyl)amino)-1-(dihydroxy Phosphate)glucopyranose

23. Q5389586

24. .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)

25. [(2r,3s,4r,5r,6r)-6-[[(2r,3s,4r,5r,6r)-4-decoxy-3-hydroxy-5-(3-oxotetradecanoylamino)-6-phosphonooxyoxan-2-yl]methoxy]-4-[(3r)-3-methoxydecoxy]-2-(methoxymethyl)-5-[[(z)-octadec-11-enoyl]amino]oxan-3-yl] Dihydrogen Phosphate

26. 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

2.4 Create Date
2006-07-04
3 Chemical and Physical Properties
Molecular Weight 1313.7 g/mol
Molecular Formula C66H126N2O19P2
XLogP315.4
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count19
Rotatable Bond Count59
Exact Mass1312.84300379 g/mol
Monoisotopic Mass1312.84300379 g/mol
Topological Polar Surface Area294 Ų
Heavy Atom Count89
Formal Charge0
Complexity1900
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in sepsis and septicemia.


Sepsis


5 Pharmacology and Biochemistry
5.1 Pharmacology

Eritoran has been shown to down-regulate the intracellular generation of pro-inflammatory cytokines IL-6 and TNF-alpha in human monocytes.


5.2 Biological Half-Life

50.4 to 62.7 hours


5.3 Mechanism of Action

Eritoran is a toll-like receptor 4 inhibitor.


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ABOUT THIS PAGE

Eritoran Manufacturers

A Eritoran manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Eritoran, including repackagers and relabelers. The FDA regulates Eritoran manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Eritoran API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Eritoran Suppliers

A Eritoran supplier is an individual or a company that provides Eritoran active pharmaceutical ingredient (API) or Eritoran finished formulations upon request. The Eritoran suppliers may include Eritoran API manufacturers, exporters, distributors and traders.

Eritoran GMP

Eritoran Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Eritoran GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Eritoran GMP manufacturer or Eritoran GMP API supplier for your needs.

Eritoran CoA

A Eritoran CoA (Certificate of Analysis) is a formal document that attests to Eritoran's compliance with Eritoran specifications and serves as a tool for batch-level quality control.

Eritoran CoA mostly includes findings from lab analyses of a specific batch. For each Eritoran CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Eritoran may be tested according to a variety of international standards, such as European Pharmacopoeia (Eritoran EP), Eritoran JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Eritoran USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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