STEARIC MONOETHANOLAMIDE

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

Structure Search

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)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22125609 | https://www.ncbi.nlm.nih.gov/pubmed/19873884 | https://www.ncbi.nlm.nih.gov/pubmed/28963942 | https://www.ncbi.nlm.nih.gov/pubmed/25033558

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
Interleukin-1 beta 22 Target ID: P01584 Gene ID: 3553.0 Gene Symbol: IL1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25033558	Inhibitor 8504
Interleukin-6 4 Target ID: P05231 Gene ID: 3569.0 Gene Symbol: IL6 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25033558	Inhibitor 8504
Tumor necrosis factor 6 Target ID: P01375 Gene ID: 7124.0 Gene Symbol: TNF Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25033558	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Burn 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19873884	Palliative	Preclinical	Unknown Approved Use Unknown
Chronic myalgia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22125609	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28963942	Preventing	Basic research	Unknown Approved Use Unknown
Skin Care 16 Sources: https://www.cir-safety.org/sites/default/files/amides032012FAR.pdf http://www.drugs-library.com/drugs/nu-skin-nu-colour.html http://www.cosmeticsinfo.org/ingredient/stearamide-mea	Inactive ingredient	Approved 8583	Nu Skin Nu Colour Approved Use Unknown

PubMed

Title	Date	PubMed
Palmitoylethanolamide and other anandamide congeners. Proposed role in the diseased brain.	2010-07	20353771
Plasma anandamide and other N-acylethanolamines are correlated with their corresponding free fatty acid levels under both fasting and non-fasting conditions in women.	2010-06-14	20546561
Genetic manipulation of palmitoylethanolamide production and inactivation in Saccharomyces cerevisiae.	2009-06-16	19529773
Synthesis and anticonvulsant activity of N-(2-hydroxy-ethyl)amide derivatives.	2009-01	19072766
A saturated N-acylethanolamine other than N-palmitoyl ethanolamine with anti-inflammatory properties: a neglected story...	2008-05	18426496
Influence of dietary fatty acids on endocannabinoid and N-acylethanolamine levels in rat brain, liver and small intestine.	2008-04	18316044
Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents.	2006-03	16517404
Effects of saturated long-chain N-acylethanolamines on voltage-dependent Ca2+ fluxes in rabbit T-tubule membranes.	2005-02-15	15639235
Stearoylethanolamide exerts anorexic effects in mice via down-regulation of liver stearoyl-coenzyme A desaturase-1 mRNA expression.	2004-10	15289450
Cannabinoid CB1 receptor activation does not prevent the toxicity of glutamate towards embryonic chick telencephalon primary cultures.	2003-11	14659458
Cannabimimetic activity, binding, and degradation of stearoylethanolamide within the mouse central nervous system.	2002-09	12359156
Binding, degradation and apoptotic activity of stearoylethanolamide in rat C6 glioma cells.	2002-08-15	12010121
Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance.	2001-09-21	11463796

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

STEARAMIDE MEA

Preferred Name

English

STEARIC MONOETHANOLAMIDE

Common Name

English

STEAROYLMONOETHANOLAMIDE

Common Name

English

STEARIC ACID MONOETHANOLAMIDE

Common Name

English

INCROMIDE SMEA

Brand Name

English

N-(2-HYDROXYETHYL)OCTADECANAMIDE

Systematic Name

English

N-(2-HYDROXYETHYL)STEARAMIDE

Systematic Name

English

STEARAMIDE MONOETHANOLAMINE

Systematic Name

English

NSC-3377

Code

English

OCTADECANAMIDE, N-(2-HYDROXYETHYL)-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

Stearoylethanolamide