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Details

Stereochemistry ACHIRAL
Molecular Formula C13H26N2O4
Molecular Weight 274.3571
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADELMIDROL

SMILES

C(CCCC(=NCCO)O)CCCC(=NCCO)O

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
Topical adelmidrol 2% emulsion, a novel aliamide, in the treatment of mild atopic dermatitis in pediatric subjects: a pilot study.
2007
Mast cell morphometry and densitometry in experimental skin wounds treated with a gel containing adelmidrol: a placebo controlled study.
2008 Jun
Effect of a mucoadhesive gel and dental scaling on gingivitis in dogs.
2008 Mar
Adelmidrol, a palmitoylethanolamide analogue, reduces chronic inflammation in a carrageenin-granuloma model in rats.
2009 Jun
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
NSC-27132
Code English
N,N'-BIS(2-HYDROXYETHYL)NONANEDIAMIDE
Systematic Name English
ADELMIDROL [INN]
Common Name English
ADELMIDROL [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29714
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
Code System Code Type Description
INN
7140
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
EVMPD
SUB05265MIG
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
MESH
C552602
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
EPA CompTox
1675-66-7
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
FDA UNII
1BUC3685QU
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL2105967
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
NCI_THESAURUS
C74098
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
PUBCHEM
176874
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY
CAS
1675-66-7
Created by admin on Fri Jun 25 22:02:30 UTC 2021 , Edited by admin on Fri Jun 25 22:02:30 UTC 2021
PRIMARY