Identification
- Generic Name
- Oleic monoethanolamide
- DrugBank Accession Number
- DB16495
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 325.537
Monoisotopic: 325.2980795 - Chemical Formula
- C20H39NO2
- Synonyms
- N-(2-Hydroxyethyl)oleamide
- N-OEA
- N-oleoyl ethanolamine
- N-oleoylethanolamine
- OEA
- Oleamide MEA
- Oleoyl Ethanolamide
- Oleoyl monoethanolamide
- Oleoylethanolamide
- Oleylethanolamide
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
- Pharmacodynamics
Not Available
- Mechanism of action
Oleoylethanolamide (OEA) is a major N-acylethanolamine and an endogenous ethanolamide fatty acid. Although it is an endocannabinoids-like compound, it does not bind to cannabinoid receptors. Instead, this lipid sensor is an agonist at peroxisome proliferator-activated receptor-α (PPAR-α) agonist while also being an inhibitor of ceramidase and thereby the sphingolipid signaling pathway.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1HI5J9N8E6
- CAS number
- 111-58-0
- InChI Key
- BOWVQLFMWHZBEF-KTKRTIGZSA-N
- InChI
- InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
- IUPAC Name
- (9Z)-N-(2-hydroxyethyl)octadec-9-enamide
- SMILES
- CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
References
- General References
- Payahoo L, Khajebishak Y, Asghari Jafarabadi M, Ostadrahimi A: Oleoylethanolamide Supplementation Reduces Inflammation and Oxidative Stress in Obese People: A Clinical Trial. Adv Pharm Bull. 2018 Aug;8(3):479-487. doi: 10.15171/apb.2018.056. Epub 2018 Aug 29. [Article]
- Di Paola M, Bonechi E, Provensi G, Costa A, Clarke G, Ballerini C, De Filippo C, Passani MB: Oleoylethanolamide treatment affects gut microbiota composition and the expression of intestinal cytokines in Peyer's patches of mice. Sci Rep. 2018 Oct 5;8(1):14881. doi: 10.1038/s41598-018-32925-x. [Article]
- Tsuboi K, Uyama T, Okamoto Y, Ueda N: Endocannabinoids and related N-acylethanolamines: biological activities and metabolism. Inflamm Regen. 2018 Oct 1;38:28. doi: 10.1186/s41232-018-0086-5. eCollection 2018. [Article]
- Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. doi: 10.1152/ajpheart.00888.2002. Epub 2003 Jan 30. [Article]
- Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. doi: 10.1006/jmcc.2002.1533. [Article]
- External Links
- Human Metabolome Database
- HMDB0002088
- ChemSpider
- 4446574
- BindingDB
- 29080
- ChEBI
- 71466
- ChEMBL
- CHEMBL280065
- ZINC
- ZINC000008034993
- PDBe Ligand
- 5YM
- PDB Entries
- 7v7w
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP 5.51 ChemAxon pKa (Strongest Acidic) 15.47 ChemAxon pKa (Strongest Basic) -1.3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 49.33 Å2 ChemAxon Rotatable Bond Count 17 ChemAxon Refractivity 100.41 m3·mol-1 ChemAxon Polarizability 42.64 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Drug created at January 21, 2021 02:01 / Updated at January 24, 2021 06:04