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Details

Stereochemistry ACHIRAL
Molecular Formula C13H26N2O4
Molecular Weight 274.3565
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADELMIDROL

SMILES

OCCNC(=O)CCCCCCCC(=O)NCCO

InChI

InChIKey=PAHZPHDAJQIETD-UHFFFAOYSA-N
InChI=1S/C13H26N2O4/c16-10-8-14-12(18)6-4-2-1-3-5-7-13(19)15-9-11-17/h16-17H,1-11H2,(H,14,18)(H,15,19)

HIDE SMILES / InChI
Adelmidrol is the synthetic derivate of azelaic acid, a naturally occurring saturated dicarboxylic acid, that is found in some whole grains and in trace amounts in the human body. Chemically, ademidrol is the N,N-bis (2-hydroxyethyl) non anediamide and it is an amphiphilic or amphipathic compound, possessing both hydrophilic and hydrophobic properties, that favor its solubility both in aqueous and organic media. Adelmidrol belongs to the aliamide family, a group of fatty acid derivatives with cannabimimetic properties, able to control mast cell (MC) hyperreactivity in several pathophysiological and pathological conditions. Pro-inflammatory NF-κB pathway were markedly reduced by treatment with adelmidrol. The anti-inflammatory effect of adelmidrol appeared to be related on PPAR-gamma activation. Adelmidrol is topically effective for human inflammatory skin disorders and is able to modulate the inflammatory response in human keratinocytes. The combination of hyaluronic acid and adelmidrol improves the signs of osteoarthritis induced by monosodium iodoacetate.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibitory effect of topical adelmidrol on antigen-induced skin wheal and mast cell behavior in a canine model of allergic dermatitis.
2012 Nov 26
Patents

Sample Use Guides

2% emulsion twice daily
Route of Administration: Topical
The concentrations of palmitoylethanolamide (PEA) and 2-arachidonoylglycerol (2-AG) were significantly increased in canine keratinocytes treated with adelmidrol (10 uM for 24 h) when compared to vehicle. Adelmidrol (10 uM) also induced a significant increase in PEA concentrations in HaCaT cells after 24 h, without altering the concentrations of the other mediators.
Name Type Language
ADELMIDROL
INN  
INN  
Official Name English
Adelmidrol [WHO-DD]
Common Name English
NSC-27132
Code English
N,N'-BIS(2-HYDROXYETHYL)NONANEDIAMIDE
Systematic Name English
adelmidrol [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29714
Created by admin on Sat Dec 16 17:28:31 GMT 2023 , Edited by admin on Sat Dec 16 17:28:31 GMT 2023
Code System Code Type Description
INN
7140
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EVMPD
SUB05265MIG
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MESH
C552602
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WIKIPEDIA
Adelmidrol
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EPA CompTox
DTXSID10168302
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NSC
27132
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FDA UNII
1BUC3685QU
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ChEMBL
CHEMBL2105967
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NCI_THESAURUS
C74098
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PUBCHEM
176874
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CAS
1675-66-7
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SMS_ID
100000087699
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