Page last updated: 2024-12-06

stearoylethanolamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Stearoylethanolamide (SEA) is a fatty acid amide that is naturally found in various tissues and fluids of the body, including the brain, where it acts as a signaling molecule. It is synthesized by the enzymatic hydrolysis of fatty acid amides, such as oleoylethanolamide (OEA), and is also produced commercially through the reaction of stearic acid with ethanolamine. SEA has been shown to exhibit a variety of biological effects, including anti-inflammatory, analgesic, and appetite-regulating properties. It has been studied extensively for its potential therapeutic benefits in conditions such as obesity, pain, and inflammation. The mechanism of action of SEA is complex and involves interactions with various receptors, including the peroxisome proliferator-activated receptor alpha (PPAR-α) and the cannabinoid receptor 1 (CB1). Its ability to modulate the activity of these receptors contributes to its diverse biological effects. SEA is also a component of some cosmetic products due to its moisturizing and skin-soothing properties. Ongoing research continues to explore the full therapeutic potential of SEA in various medical applications.'

N-(octadecanoyl)ethanolamine : An N-acylethanolamine 18:0 that is the ethanolamide of octadecanoic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID27902
CHEMBL ID171447
CHEBI ID85299
SCHEMBL ID50178
MeSH IDM0439489

Synonyms (84)

Synonym
bdbm50074620
octadecanoic acid (2-hydroxy-ethyl)-amide
stearic ethylolamide
stearoylethanolamine
stearic monoethanolamine
octadecanamide, n-(2-hydroxyethyl)-
stearoyl monoethanolamide
111-57-9
stearic monoethanolamide
clindrol 200-ms
cycloamide sm
n-(2-hydroxyethyl)octadecanamide
nsc3377
stearic ethanolamide
stearoylmonoethanolamide
stearamyl
comperlan hs
nsc-3377
stearic acid monoethanolamide
n-stearoylethanolamine
n-(2-hydroxyethyl)stearamide
loramine s 280
monoethanolamine stearic acid amide
marlamid m 18
stearamide mea
n-(hydroxyethyl)stearamide
nsc-52619
nsc52619
n-(2-hydroxyethyl)-octadecanamide
stearoyl ethanolamide, >=98%, crystalline
sea
nae 18:0
chebi:85299 ,
n-stearoylethanolamide
CHEMBL171447 ,
stearoyl-ea
LMFA08040051
n-(octadecanoyl)-ethanolamine
stearoyl-ethanolamine
AKOS002676465
ec 203-883-2
nsc 3377
einecs 203-883-2
stearoylethanolamide
03xv449q24 ,
ceramid
unii-03xv449q24
n-(2-hydroxyethyl)stearoylamide
FT-0631626
stearamide mea [inci]
stearamide monoethanolamine
incromide smea
8038-89-9
gtpl3621
STL454871
SCHEMBL50178
stearoyl ethanolamide
n-(otadecanoyl)-ethanolamine
n-(octadecanoyl)ethanolamine
n-octadecanoyl ethanolamine
n-octadecanoylethanolamine
witcamide 70
stearamide-mea (1:1)
rewomid s 280
amidex sme
stearamide, n-(2-hydroxyethyl)-
alkamide s-280
1:1 stearamide mea
monamid s
mackamide sma
W-109411
HMS3649H17
DTXSID9042178
nae(18:0)
HY-113015
CS-0059359
octadecanoyl ethanolamide
SR-01000946662-1
sr-01000946662
Q15427850
stearic acid ethanolamide
MS-24898
EN300-18537220
Z3222444503
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylethanolamine 18:0A N-(long-chain-acyl)ethanolamine in which the acyl group contains 18 carbons and is fully saturated.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki0.21700.00020.566510.0000AID49674
Transient receptor potential cation channel subfamily V member 2Rattus norvegicus (Norway rat)IC50 (µMol)10.00000.03701.93458.6000AID1400243; AID1400244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID49674Tested for binding affinity to Cannabinoid receptor 11999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID1189980Antiproliferative activity against human NCI-H460 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1189968Antiproliferative activity against human MCF7 cells after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1189982Antiproliferative activity against human OVCAR3 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1189973Antiproliferative activity against human OVCAR3 cells after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1189969Antiproliferative activity against human NCI/ADR-RES cells after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID307156Solubility in ethanol2007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine.
AID1238063Agonist activity at Gal4-tagged human PPARalpha expressed in HEK293 cells at 3 to 30 uM incubated for 16 to 20 hrs by luciferase and beta-galactosidase activity based reporter gene assay2015Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16
Design and synthesis of silicon-containing fatty acid amide derivatives as novel peroxisome proliferator-activated receptor (PPAR) agonists.
AID1189978Antiproliferative activity against human NCI/ADR-RES cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1189972Antiproliferative activity against human PC3 cells after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID307158Stimulation of cytyledon expansion in cucumber after 3 days2007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine.
AID1189976Antiproliferative activity against human U251 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1238065Agonist activity at Gal4-tagged human PPARgamma expressed in HEK293 cells at 3 to 30 uM incubated for 16 to 20 hrs by luciferase and beta-galactosidase activity based reporter gene assay2015Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16
Design and synthesis of silicon-containing fatty acid amide derivatives as novel peroxisome proliferator-activated receptor (PPAR) agonists.
AID1189967Antiproliferative activity against human U251 cells after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID725618Displacement of [3H]resiniferatoxin from TRPV1 in mouse cortical slices2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Novel acylethanolamide derivatives that modulate body weight through enhancement of hypothalamic pro-opiomelanocortin (POMC) and/or decreased neuropeptide Y (NPY).
AID38685Tested for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID1189974Cytotoxicity against human HaCaT cells after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID38682Tested for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID1189981Antiproliferative activity against human PC3 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1400243Antagonist activity at recombinant rat TRPV2 expressed in HEK293 cells assessed as inhibition of LPC-induced Ca2+ levels preincubated for 5 mins followed by agonist addition by Fuo-4-AM based spectrofluorimetry2018Journal of medicinal chemistry, 09-27, Volume: 61, Issue:18
Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.
AID307157Stimulation of hypocotyls elongation in rape after 3 days2007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine.
AID1400244Antagonist activity at recombinant rat TRPV2 expressed in HEK293 cells assessed as inhibition of CBD-induced Ca2+ levels preincubated for 5 mins followed by agonist addition by Fuo-4-AM based spectrofluorimetry2018Journal of medicinal chemistry, 09-27, Volume: 61, Issue:18
Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.
AID1189977Antiproliferative activity against human MCF7 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1189979Antiproliferative activity against human 786-0 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID1189983Cytotoxicity against human HaCaT cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay2015Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2
Antiproliferative activity of synthetic fatty acid amides from renewable resources.
AID307159Stimulation of coleoptiles growth in common wheat after 18 to 20 hrs2007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine.
AID307155Solubility in ethyl acetate solution2007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine.
AID307154Solubility in chloroform2007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (2.33)18.2507
2000's10 (23.26)29.6817
2010's27 (62.79)24.3611
2020's5 (11.63)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.12

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index35.12 (24.57)
Research Supply Index4.32 (2.92)
Research Growth Index5.65 (4.65)
Search Engine Demand Index47.56 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.12)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (2.78%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other70 (97.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]