Adelmidrol
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 329603

CAS#: 1675-66-7

Description: Adelmidrol is the semisynthetic diethanolamide derivative of azelaic acid, and has a symmetrical chemical structure. It classed as an ALIAmide, and is similar to palmitoylethanolamide, the parent molecule in the ALIAmide class of drugs. It is used extensively in Italy in veterinary medicine, to treat skin inflammation. In 2015 it was found the compound also exerts anti-inflammatory action given systemically in 10 mg per kg bodyweigh

Chemical Structure

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Adelmidrol
CAS# 1675-66-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329603
Name: Adelmidrol
CAS#: 1675-66-7
Chemical Formula: C13H26N2O4
Exact Mass: 274.19
Molecular Weight: 274.361
Elemental Analysis: C, 56.91; H, 9.55; N, 10.21; O, 23.33

Price and Availability

Size Price Availability Quantity
200mg USD 450 2 Weeks
500mg USD 850 2 Weeks
1g USD 1450 2 Weeks
2g USD 2650 2 Weeks
5g USD 4650 2 Weeks
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Synonym: Adelmidrol

IUPAC/Chemical Name: N,N'-bis(2-Hydroxyethyl)nonanediamide

InChi Key: PAHZPHDAJQIETD-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(NCCO)CCCCCCCC(NCCO)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: ALIAmides are group of fatty acid derivatives with cannabimimetic properties, which have antiinflammatory and analgesic effects and are thought to act by reducing mast cell activation

Product Data:
Product Data
Instruction:
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Biological target: Adelmidrol exerts anti-inflammatory effects that are partly dependent on PPARγ. Adelmidrol reduces NF-κB translocation, and COX-2 expression.
In vitro activity: PEA concentrations were significantly increased in HEK-WT cells treated with adelmidrol 10 µM, compared to vehicle, although only after 24 h (Fig. 3A). In HEK-NAAA cells, baseline PEA concentrations were significantly lower than in HEK-WT cells, in agreement with the role of active NAAA in the tonic degradation of this mediator. PEA concentrations were significantly decreased in HEK-NAAA cells treated with adelmidrol for 40 min and there was a trend (P = 0.07) after 24 h, compared to vehicle (Fig. 3B). Reference: Vet J. 2016 Jan;207:85-91. https://pubmed.ncbi.nlm.nih.gov/26639824/
In vivo activity: Twenty-one days after bleomycin instillation, adelmidrol administration reduced the number of inflammatory cells in the bronchoalveolar lavage fluid compared to the vehicle-treated mice (Figure 1A). In particular, this study evaluated macrophages, neutrophils, lymphocytes, and eosinophils, observing a significant rise in cell numbers in bronchoalveolar lavage collected from vehicle-treated animals compared to the sham groups. Adelmidrol treatment was able to reduce the airway infiltration by inflammatory cells (Figure 1B). An analysis of cytokine expressions in the bronchoalveolar lavage fluid showed that pulmonary fibrosis increased IL,6 IL-1β, TNF-α, and TGF-1β expressions compared to the sham groups. In the bronchoalveolar lavage fluid collected from adelmidrol-treated mice, a reduced expression of IL,6 IL-1β, TNF-α, and TGF-1β was detected (Figure 1C–F). Reference: Antioxidants (Basel). 2020 Jul; 9(7): 601. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7402091/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 77.5 282.47
Ethanol 28.0 102.06
Water 55.0 200.47

Preparing Stock Solutions

The following data is based on the product molecular weight 274.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Petrosino S, Puigdemont A, Della Valle MF, Fusco M, Verde R, Allarà M, Aveta T, Orlando P, Di Marzo V. Adelmidrol increases the endogenous concentrations of palmitoylethanolamide in canine keratinocytes and down-regulates an inflammatory reaction in an in vitro model of contact allergic dermatitis. Vet J. 2016 Jan;207:85-91. doi: 10.1016/j.tvjl.2015.10.060. Epub 2015 Nov 10. PMID: 26639824. 2. Fusco R, Cordaro M, Genovese T, Impellizzeri D, Siracusa R, Gugliandolo E, Peritore AF, D'Amico R, Crupi R, Cuzzocrea S, Di Paola R. Adelmidrol: A New Promising Antioxidant and Anti-Inflammatory Therapeutic Tool in Pulmonary Fibrosis. Antioxidants (Basel). 2020 Jul 9;9(7):601. doi: 10.3390/antiox9070601. PMID: 32660140; PMCID: PMC7402091. 3. Nageeb MM, Khatab MI, Abdel-Sameea AA, Teleb NA. Adelmidrol protects against non-alcoholic steatohepatitis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2020 May;393(5):777-784. doi: 10.1007/s00210-019-01785-1. Epub 2019 Dec 18. PMID: 31853615.
In vitro protocol: 1. Petrosino S, Puigdemont A, Della Valle MF, Fusco M, Verde R, Allarà M, Aveta T, Orlando P, Di Marzo V. Adelmidrol increases the endogenous concentrations of palmitoylethanolamide in canine keratinocytes and down-regulates an inflammatory reaction in an in vitro model of contact allergic dermatitis. Vet J. 2016 Jan;207:85-91. doi: 10.1016/j.tvjl.2015.10.060. Epub 2015 Nov 10. PMID: 26639824.
In vivo protocol: 1. Fusco R, Cordaro M, Genovese T, Impellizzeri D, Siracusa R, Gugliandolo E, Peritore AF, D'Amico R, Crupi R, Cuzzocrea S, Di Paola R. Adelmidrol: A New Promising Antioxidant and Anti-Inflammatory Therapeutic Tool in Pulmonary Fibrosis. Antioxidants (Basel). 2020 Jul 9;9(7):601. doi: 10.3390/antiox9070601. PMID: 32660140; PMCID: PMC7402091. 2. Nageeb MM, Khatab MI, Abdel-Sameea AA, Teleb NA. Adelmidrol protects against non-alcoholic steatohepatitis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2020 May;393(5):777-784. doi: 10.1007/s00210-019-01785-1. Epub 2019 Dec 18. PMID: 31853615.

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1: Guida F, Rocco M, Luongo L, Persiani P, Vulpiani MC, Nusca SM, Maione S, Coluzzi F. Targeting Neuroinflammation in Osteoarthritis with Intra-Articular Adelmidrol. Biomolecules. 2022 Oct 11;12(10):1453. doi: 10.3390/biom12101453. PMID: 36291664; PMCID: PMC9599300.


2: Nageeb MM, Khatab MI, Abdel-Sameea AA, Teleb NA. Adelmidrol protects against non-alcoholic steatohepatitis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2020 May;393(5):777-784. doi: 10.1007/s00210-019-01785-1. Epub 2019 Dec 18. PMID: 31853615.


3: Del Re A, Palenca I, Seguella L, Pesce M, Corpetti C, Steardo L, Rurgo S, Sarnelli G, Esposito G. Oral Adelmidrol Administration Up-Regulates Palmitoylethanolamide Production in Mice Colon and Duodenum through a PPAR-γ Independent Action. Metabolites. 2022 May 19;12(5):457. doi: 10.3390/metabo12050457. PMID: 35629962; PMCID: PMC9144287.


4: Fusco R, Cordaro M, Genovese T, Impellizzeri D, Siracusa R, Gugliandolo E, Peritore AF, D'Amico R, Crupi R, Cuzzocrea S, Di Paola R. Adelmidrol: A New Promising Antioxidant and Anti-Inflammatory Therapeutic Tool in Pulmonary Fibrosis. Antioxidants (Basel). 2020 Jul 9;9(7):601. doi: 10.3390/antiox9070601. PMID: 32660140; PMCID: PMC7402091.


5: Impellizzeri D, Di Paola R, Cordaro M, Gugliandolo E, Casili G, Morittu VM, Britti D, Esposito E, Cuzzocrea S. Adelmidrol, a palmitoylethanolamide analogue, as a new pharmacological treatment for the management of acute and chronic inflammation. Biochem Pharmacol. 2016 Nov 1;119:27-41. doi: 10.1016/j.bcp.2016.09.001. Epub 2016 Sep 4. PMID: 27599446.


6: Interdonato L, D'amico R, Cordaro M, Siracusa R, Fusco R, Peritore AF, Gugliandolo E, Crupi R, Coaccioli S, Genovese T, Impellizzeri D, Di Paola R, Cuzzocrea S. Aerosol-Administered Adelmidrol Attenuates Lung Inflammation in a Murine Model of Acute Lung Injury. Biomolecules. 2022 Sep 16;12(9):1308. doi: 10.3390/biom12091308. PMID: 36139146; PMCID: PMC9496587.


7: Di Paola R, Fusco R, Impellizzeri D, Cordaro M, Britti D, Morittu VM, Evangelista M, Cuzzocrea S. Adelmidrol, in combination with hyaluronic acid, displays increased anti-inflammatory and analgesic effects against monosodium iodoacetate-induced osteoarthritis in rats. Arthritis Res Ther. 2016 Dec 12;18(1):291. doi: 10.1186/s13075-016-1189-5. PMID: 27955699; PMCID: PMC5153857.


8: Cordaro M, Impellizzeri D, Gugliandolo E, Siracusa R, Crupi R, Esposito E, Cuzzocrea S. Adelmidrol, a Palmitoylethanolamide Analogue, as a New Pharmacological Treatment for the Management of Inflammatory Bowel Disease. Mol Pharmacol. 2016 Nov;90(5):549-561. doi: 10.1124/mol.116.105668. Epub 2016 Sep 13. PMID: 27625036.


9: Petrosino S, Puigdemont A, Della Valle MF, Fusco M, Verde R, Allarà M, Aveta T, Orlando P, Di Marzo V. Adelmidrol increases the endogenous concentrations of palmitoylethanolamide in canine keratinocytes and down-regulates an inflammatory reaction in an in vitro model of contact allergic dermatitis. Vet J. 2016 Jan;207:85-91. doi: 10.1016/j.tvjl.2015.10.060. Epub 2015 Nov 10. PMID: 26639824.


10: De Filippis D, D'Amico A, Cinelli MP, Esposito G, Di Marzo V, Iuvone T. Adelmidrol, a palmitoylethanolamide analogue, reduces chronic inflammation in a carrageenin-granuloma model in rats. J Cell Mol Med. 2009 Jun;13(6):1086-95. doi: 10.1111/j.1582-4934.2008.00353.x. Epub 2008 Apr 18. PMID: 18429935; PMCID: PMC4496105.


11: Ostardo E, Impellizzeri D, Cervigni M, Porru D, Sommariva M, Cordaro M, Siracusa R, Fusco R, Gugliandolo E, Crupi R, Schievano C, Inferrera A, Di Paola R, Cuzzocrea S; Urology Study Group. Adelmidrol + sodium hyaluronate in IC/BPS or conditions associated to chronic urothelial inflammation. A translational study. Pharmacol Res. 2018 Aug;134:16-30. doi: 10.1016/j.phrs.2018.05.013. Epub 2018 May 22. PMID: 29800607.


12: Campolo M, Siracusa R, Cordaro M, Filippone A, Gugliandolo E, Peritore AF, Impellizzeri D, Crupi R, Paterniti I, Cuzzocrea S. The association of adelmidrol with sodium hyaluronate displays beneficial properties against bladder changes following spinal cord injury in mice. PLoS One. 2019 Jan 17;14(1):e0208730. doi: 10.1371/journal.pone.0208730. PMID: 30653511; PMCID: PMC6336272.


13: Cerrato S, Brazis P, Della Valle MF, Miolo A, Puigdemont A. Inhibitory effect of topical adelmidrol on antigen-induced skin wheal and mast cell behavior in a canine model of allergic dermatitis. BMC Vet Res. 2012 Nov 26;8:230. doi: 10.1186/1746-6148-8-230. PMID: 23181761; PMCID: PMC3540011.


14: Teobaldi I, Stoico V, Perrone F, Mantovani A, Piccagli P, Grandi F, Baldo B. Effect of a Topical Gel Based on Adelmidrol + Trans-Traumatic Acid in the Treatment of Diabetic Foot Ulcers: An Open-Label Study. J Am Podiatr Med Assoc. 2022 Mar 16;112(1):20-143. doi: 10.7547/20-143. PMID: 34709395.


15: Siracusa R, Impellizzeri D, Cordaro M, Gugliandolo E, Peritore AF, Di Paola R, Cuzzocrea S. Topical Application of Adelmidrol + Trans-Traumatic Acid Enhances Skin Wound Healing in a Streptozotocin-Induced Diabetic Mouse Model. Front Pharmacol. 2018 Aug 23;9:871. doi: 10.3389/fphar.2018.00871. PMID: 30190675; PMCID: PMC6115498.


16: Indraccolo U, Scutiero G, Matteo M, Greco P. Effectiveness of vaginal adelmidrol for treating pelvic visceral discomforts and anxiety: a prospective observational study. Minerva Ginecol. 2013 Aug;65(4):465-70. PMID: 24051946.


17: D'Amico R, Siracusa R, Fusco R, Cordaro M, Genovese T, Peritore AF, Gugliandolo E, Crupi R, Impellizzeri D, Cuzzocrea S, Paola RD. Protective effects of Colomast®, A New Formulation of Adelmidrol and Sodium Hyaluronate, in A Mouse Model of Acute Restraint Stress. Int J Mol Sci. 2020 Oct 30;21(21):8136. doi: 10.3390/ijms21218136. PMID: 33143356; PMCID: PMC7662642.


18: Karatzi C, Stefanidou M, Chaniotis V, Evangelou G, Krueger-Krasagakis S, Krasagakis K. Treatment of giant vulvar syringomas with topical adelmidrol: The role of mast cells. Australas J Dermatol. 2018 Nov;59(4):e305-e307. doi: 10.1111/ajd.12850. Epub 2018 Jun 4. PMID: 29863277.


19: Pulvirenti N, Nasca MR, Micali G. Topical adelmidrol 2% emulsion, a novel aliamide, in the treatment of mild atopic dermatitis in pediatric subjects: a pilot study. Acta Dermatovenerol Croat. 2007;15(2):80-3. PMID: 17631786.


20: Abramo F, Salluzzi D, Leotta R, Auxilia S, Noli C, Miolo A, Mantis P, Lloyd DH. Mast cell morphometry and densitometry in experimental skin wounds treated with a gel containing adelmidrol: a placebo controlled study. Wounds. 2008 Jun;20(6):149-57. PMID: 25942520.