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Ethanolamine Oleate

July 24, 2017
Common Name

Ethanolamine Oleate Description

Ethanolamine Oleate is only found in individuals that have used or taken this drug. It is a mild sclerosing agent. It is composed of ethanolamine, a basic substance, which when combined with oleic acid forms a clear, straw to pale yellow colored, deliquescent oleate.The oleic acid component of ethanolamine oleate is responsible for the inflammatory response, and may also activate coagliation in vivo by release of tissue factor and activation of Hageman factor. The ethanolamine component, however, may inhibit fibrin clot formation by chelating calcium, so that a procoagliant action of ethanolamine oleate has not been demonstrated. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source Monoethanolamine oleateKegg EthamolinKegg OldaminKegg Monoethanolamine oleic acidGenerator Ethanolamine oleic acidGenerator beta-Hydroxyethylammonium oleateHMDB cis-9-Octadecenoic acid, ethanolamine saltHMDB

Chemical Formlia

C20H41NO3 Average Molecliar Weight

343.5444 Monoisotopic Molecliar Weight

343.308644183 IUPAC Name

(9Z)-octadec-9-enoic acid; 2-aminoethan-1-ol Traditional Name

ethanolamine; oleic acid CAS Registry Number

2272-11-9 SMILES

NCCO.CCCCCCCCC=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O2.C2H7NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;3-1-2-4/h9-10H,2-8,11-17H2,1H3,(H,19,20);4H,1-3H2/b10-9-;

InChI Key

KGWDUNBJIMUFAP-KVVVOXFISA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Fatty Acyls Direct Parent

Long-chain fatty acids Alternative Parents

  • Unsaturated fatty acids
  • Straight chain fatty acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound

    • Molecliar Framework

    Not Available External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Sclerosing Solutions

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source logP6.78ChemAxon pKa (Strongest Acidic)4.99ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area37.3 Å2ChemAxon Rotatable Bond Count16ChemAxon Refractivity87.4 m3·mol-1ChemAxon Polarizability37.09 Å3ChemAxon Number of Rings0ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06689

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06689

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06689 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4445632 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Monoethanolamine_oleate NuGOwiki Link

    HMDB15638 Metagene Link

    HMDB15638 METLIN ID

    Not Available PubChem Compound

    5282489 PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Hydroxyzine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Kang JH, Kambayashi J, Sakon M, Shiozaki H, Ogawa Y, Ohshiro T, Mori T: Mechanism of the haemostatic effect of ethanolamine oleate in the injection sclerotherapy for oesophageal varices. Br J Surg. 1987 Jan;74(1):50-3. [PubMed:3828735 ]
    2. Seidman E, Weber AM, Morin CL, Ethier R, Lamarche JB, Guerguerian AJ, Geoffroy G, Roy CC: Spinal cord paralysis following sclerotherapy for esophageal varices. Hepatology. 1984 Sep-Oct;4(5):950-4. [PubMed:6332769 ]
    3. Masaki M, Mitsuhashi H, Kondo Y, Suzuki S, Wada T: [Effects of embolizing agent (ethanolamine oleate; EO) on esophageal varices with special reference to endothelial injury]. Nihon Shokakibyo Gakkai Zasshi. 1984 Jun;81(6):1491. [PubMed:6471550 ]
    4. Howard ER, Stamatakis JD, Mowat AP: Management of esophageal varices in children by injection sclerotherapy. J Pediatr Surg. 1984 Feb;19(1):2-5. [PubMed:6607986 ]
    5. Zuberi BF, Baloch Q: Comparison of endoscopic variceal sclerotherapy alone and in combination with octreotide in controlling acute variceal hemorrhage and early rebleeding in patients with low-risk cirrhosis. Am J Gastroenterol. 2000 Mar;95(3):768-71. [PubMed:10710072 ]
    6. Meirelles-Santos JO, Carvalho AF Jr, Callejas-Neto F, Magna LA, Yamanaka A, Zeitune JM, Brandalise NA, Ferraz JG: Absolute ethanol and 5% ethanolamine oleate are comparable for sclerotherapy of esophageal varices. Gastrointest Endosc. 2000 May;51(5):573-6. [PubMed:10805844 ]
    7. VOIGT J: [Allergy to varex (monoethanolamine oleate)]. Ugeskr Laeger. 1954 Mar 25;116(12):452-7. [PubMed:13169341 ]
    8. VOIGT J: [Fatal allergic shock after injection of Varex (monoethanolamine-oleate). On the risks of injection treatment]. Ugeskr Laeger. 1963 Jun 21;125:896-8. [PubMed:13997698 ]
    9. PACCA ML: [Antihyaluronidase activity of monoethanolamine oleate]. Boll Soc Ital Biol Sper. 1951 Mar-Apr;27(4):576-9. [PubMed:14869471 ]
    10. NOORDIJK JA: [Monoethanolamine oleate]. Ned Tijdschr Geneeskd. 1950 Apr 22;94(16):1110-1. [PubMed:15416877 ]
    11. Yamamoto K, Sakaguchi H, Anai H, Tanaka T, Morimoto K, Kichikawa K, Uchida H: Sclerotherapy for simple cysts with use of ethanolamine oleate: preliminary experience. Cardiovasc Intervent Radiol. 2005 Nov-Dec;28(6):751-5. [PubMed:16132390 ]
    12. Takuma Y, Nouso K, Takayama H, Makino Y, Saito S, Tanaka S, Ogata M, Ohta T, Kubota J, Iwamuro M: Gastric ulcer after prophylactic balloon-occluded retrograde transvenous obliteration. J Gastroenterol. 2007 Mar;42(3):257-60. Epub 2007 Mar 30. [PubMed:17380286 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
    Gene Name:
    CYP2E1
    Uniprot ID:
    P05181
    Molecular weight:
    56848.42
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in serine-type endopeptidase activity
    Specific function:
    Factor XII is a serum glycoprotein that participates in the initiation of blood coagulation, fibrinolysis, and the generation of bradykinin and angiotensin. Prekallikrein is cleaved by factor XII to form kallikrein, which then cleaves factor XII first to alpha-factor XIIa and then trypsin cleaves it to beta- factor XIIa. Alpha-factor XIIa activates factor XI to factor XIa
    Gene Name:
    F12
    Uniprot ID:
    P00748
    Molecular weight:
    67817.6
    References
    1. Takada K, Matsumoto A, Miyoshi H, Oshiba S: Changes in thrombin-antithrombin III complex after endoscopic injection sclerotherapy. Am J Gastroenterol. 1991 Jan;86(1):123-4. [PubMed:1986546 ]
    2. Kang JH, Kambayashi J, Sakon M, Shiozaki H, Ogawa Y, Ohshiro T, Mori T: Mechanism of the haemostatic effect of ethanolamine oleate in the injection sclerotherapy for oesophageal varices. Br J Surg. 1987 Jan;74(1):50-3. [PubMed:3828735 ]

    PMID: 11125018

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