| 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 |
MOL RATIO
1 MOL RATIO (average) |
| 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
PubMed
Sample Use Guides
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
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.