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
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)
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2459 |
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Target ID: map04064 |
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Target ID: GO:0002537 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18429935 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17631786
2% emulsion twice daily
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26639824
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.
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NCI_THESAURUS |
C29714
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ACTIVE MOIETY