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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 of STEARIC MONOETHANOLAMIDE

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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P01584
Gene ID: 3553.0
Gene Symbol: IL1B
Target Organism: Homo sapiens (Human)
Target ID: P05231
Gene ID: 3569.0
Gene Symbol: IL6
Target Organism: Homo sapiens (Human)
Target ID: P01375
Gene ID: 7124.0
Gene Symbol: TNF
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Cannabimimetic activity, binding, and degradation of stearoylethanolamide within the mouse central nervous system.
2002 Sep
Genetic manipulation of palmitoylethanolamide production and inactivation in Saccharomyces cerevisiae.
2009 Jun 16
Palmitoylethanolamide and other anandamide congeners. Proposed role in the diseased brain.
2010 Jul
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

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:58 GMT 2023
Record UNII
03XV449Q24
Record Status Validated (UNII)
Record Version
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Name Type Language
STEARIC MONOETHANOLAMIDE
Common Name English
STEAROYLMONOETHANOLAMIDE
Common Name English
STEARAMIDE MEA
INCI  
INCI  
Official 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
STEARAMIDE MEA [INCI]
Common Name English
Code System Code Type Description
WIKIPEDIA
Stearoylethanolamide
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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FDA UNII
03XV449Q24
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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RXCUI
1426353
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
PRIMARY RxNorm
CHEBI
85299
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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ECHA (EC/EINECS)
203-883-2
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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EPA CompTox
DTXSID9042178
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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DAILYMED
03XV449Q24
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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NSC
3377
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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CAS
111-57-9
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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PUBCHEM
27902
Created by admin on Fri Dec 15 15:34:58 GMT 2023 , Edited by admin on Fri Dec 15 15:34:58 GMT 2023
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