Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H41NO2 |
Molecular Weight | 327.545 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCCC(=O)NCCO
InChI
InChIKey=OTGQIQQTPXJQRG-UHFFFAOYSA-N
InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)
Molecular Formula | C20H41NO2 |
Molecular Weight | 327.545 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Stearic monoethanolamide (widely known as N-stearoylethanolamine, NSE) is a biologically active cell membrane component with anti-inflammatory and membrane-protective properties. Preliminary data from a model of experimental burn in rats have shown that N-stearoylethanolamine externally applied has an anti-inflammatory effect. A significant decrease of cytokines (IL-1beta, IL-6, and TNF-alpha) levels under the NSE action, it could be one of the mechanisms of its anti-inflammatory action. The large increase in the level of N-stearoylethanolamine in myalgic muscles may reflect an attempt by the body to counteract noxious processes and activation of nociceptors because of the myalgia. If this is the case, then compound preventing their breakdown N-stearoylethanolamine may be useful analgesics for this indication. In addition, recently was studied the therapeutic potential of NSE for prevention of cognitive disfunction caused by neuroinflammation or autoimmune reaction that allowed suggesting this drug as a candidate for the treatment or prophylaxis of Alzheimer's pathology.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P01584 Gene ID: 3553.0 Gene Symbol: IL1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25033558 |
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Target ID: P05231 Gene ID: 3569.0 Gene Symbol: IL6 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25033558 |
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Target ID: P01375 Gene ID: 7124.0 Gene Symbol: TNF Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25033558 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19873884 |
Palliative | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Inactive ingredient | Nu Skin Nu Colour Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Cannabimimetic activity, binding, and degradation of stearoylethanolamide within the mouse central nervous system. | 2002 Sep |
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Genetic manipulation of palmitoylethanolamide production and inactivation in Saccharomyces cerevisiae. | 2009 Jun 16 |
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Palmitoylethanolamide and other anandamide congeners. Proposed role in the diseased brain. | 2010 Jul |
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Plasma anandamide and other N-acylethanolamines are correlated with their corresponding free fatty acid levels under both fasting and non-fasting conditions in women. | 2010 Jun 14 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19873884
burn injury in rats: the animals after the thermal burn of the skin received per os during 7 days the water suspension of N-stearoylethanolamine (NSE) in a doze 10 mg/kg of body weight.
Route of Administration:
Transdermal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25997585
It was estimated the effect of N-Stearoylethanolamine (NSE, STEARIC MONOETHANOLAMIDE) on inflammatory cytokines mRNA level (leukemia cells L1210), cytokines content (serum and LPS-stimulated macrophages) and nuclear translocation of NF-κB (peritoneal macrophages LPS-stimulated and isolated from rats with obesity-induced insulin resistance). The results indicated that NSE dose-dependently inhibits the IL-1 and IL-6 mRNA level in L1210 cells. Furthermore, the NSE treatment triggered a normalization of serum TNF-α level in insulin resistant rats and a reduction of medium IL-1 level in LPS-activated peritoneal macrophages.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:34:58 GMT 2023
by
admin
on
Fri Dec 15 15:34:58 GMT 2023
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Record UNII |
03XV449Q24
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Record Status |
Validated (UNII)
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Record Version |
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Stearoylethanolamide
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85299
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203-883-2
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