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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

Molecular Formula C13H26N2O4
Molecular Weight 274.3565
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:51:11 UTC 2023
Edited
by admin
on Thu Jul 06 22:51:11 UTC 2023
Record UNII
1BUC3685QU
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
Code System Code Type Description
INN
7140
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
PRIMARY
EVMPD
SUB05265MIG
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
PRIMARY
MESH
C552602
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
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WIKIPEDIA
Adelmidrol
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID10168302
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
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NSC
27132
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
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FDA UNII
1BUC3685QU
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
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ChEMBL
CHEMBL2105967
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
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NCI_THESAURUS
C74098
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
PRIMARY
PUBCHEM
176874
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
PRIMARY
CAS
1675-66-7
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
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SMS_ID
100000087699
Created by admin on Thu Jul 06 22:51:11 UTC 2023 , Edited by admin on Thu Jul 06 22:51:11 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY