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Identification
NameEthanolamine Oleate
Accession NumberDB06689
TypeSmall Molecule
GroupsApproved
DescriptionEthanolamine Oleate 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.
Structure
Thumb
Synonyms
beta-Hydroxyethylammonium oleate
Ethamolin
Ethanolamine oleate
Monoethanolamine oleate
Oldamin
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ethamolininjection, solution50 mg/mLintravenousQOL Medical, LLC.1998-12-22Not applicableUs
Ethanolamine Oleate Inj 50mg/mlliquid50 mgintravenousBlock Drug Company (Canada) Ltd.1992-12-312001-04-17Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MonolateNot Available
MoraminNot Available
NeosclerolNot Available
OldaminNot Available
VaricetinNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIU4RY8MRX7C
CAS number2272-11-9
WeightAverage: 343.5444
Monoisotopic: 343.308644183
Chemical FormulaC20H41NO3
InChI KeyInChIKey=KGWDUNBJIMUFAP-KVVVOXFISA-N
InChI
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-;
IUPAC Name
(9Z)-octadec-9-enoic acid; 2-aminoethan-1-ol
SMILES
NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • 1,2-aminoalcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of patients with esophageal varices that have recently bled, to prevent rebleeding.
PharmacodynamicsWhen injected intravenously, ethanolamine oleate acts primarily by irritation of the intimal endothelium of the vein and produces a sterile dose-related inflammatory response. This results in fibrosis and possible occlusion of the vein. Ethanolamine oleate also rapidly diffuses through the venous wall and produces a dose-related extravascular inflammatory reaction.
Mechanism of actionThe oleic acid component of ethanolamine oleate is responsible for the inflammatory response, and may also activate coagulation 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 procoagulant action of ethanolamine oleate has not been demonstrated.
Related Articles
AbsorptionAfter injection into an esophageal varix, ethanolamine oleate is cleared from the injection site within five minutes via the portal vein. Some of the medication also flows into the azygos vein through the periesophageal vein if more than 20 mL is injected.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThe minimum lethal dose administered intravenously to rabbits is 130 mg/kg. Overdosage can result in severe intramural necrosis of the esophagus. Complications resulting from such overdosage have resulted in death. LD50 (intravenous) in rats is 156 mg/kg. LD50 (intravenous) in dogs is 175 mg/kg.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9805
Blood Brain Barrier-0.6473
Caco-2 permeable-0.5672
P-glycoprotein substrateSubstrate0.6703
P-glycoprotein inhibitor INon-inhibitor0.959
P-glycoprotein inhibitor IINon-inhibitor0.9592
Renal organic cation transporterNon-inhibitor0.8873
CYP450 2C9 substrateNon-substrate0.853
CYP450 2D6 substrateNon-substrate0.7411
CYP450 3A4 substrateNon-substrate0.7548
CYP450 1A2 substrateInhibitor0.6639
CYP450 2C9 inhibitorNon-inhibitor0.9248
CYP450 2D6 inhibitorNon-inhibitor0.8421
CYP450 2C19 inhibitorNon-inhibitor0.9104
CYP450 3A4 inhibitorNon-inhibitor0.8594
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9496
Ames testNon AMES toxic0.9378
CarcinogenicityNon-carcinogens0.8135
BiodegradationReady biodegradable0.7487
Rat acute toxicity1.5407 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9046
hERG inhibition (predictor II)Non-inhibitor0.8212
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous50 mg/mL
Liquidintravenous50 mg
Prices
Unit descriptionCostUnit
Ethamolin 5% ampul86.62USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. NOORDIJK JA: [Monoethanolamine oleate]. Ned Tijdschr Geneeskd. 1950 Apr 22;94(16):1110-1. [PubMed:15416877 ]
  2. 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 ]
  3. PACCA ML: [Antihyaluronidase activity of monoethanolamine oleate]. Boll Soc Ital Biol Sper. 1951 Mar-Apr;27(4):576-9. [PubMed:14869471 ]
  4. 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 ]
  5. VOIGT J: [Allergy to varex (monoethanolamine oleate)]. Ugeskr Laeger. 1954 Mar 25;116(12):452-7. [PubMed:13169341 ]
  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. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  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. 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 ]
External Links
ATC CodesC05BB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ClotrimazoleThe metabolism of Ethanolamine Oleate can be decreased when combined with Clotrimazole.
Cyproterone acetateThe serum concentration of Ethanolamine Oleate can be decreased when it is combined with Cyproterone acetate.
DisulfiramThe metabolism of Ethanolamine Oleate can be decreased when combined with Disulfiram.
IsoniazidThe metabolism of Ethanolamine Oleate can be decreased when combined with Isoniazid.
NicotineThe metabolism of Ethanolamine Oleate can be decreased when combined with Nicotine.
TiclopidineThe metabolism of Ethanolamine Oleate can be decreased when combined with Ticlopidine.
Food InteractionsNot Available

Targets

Kind
Small molecule
Organism
Human
Pharmacological action
unknown
Actions
chelator
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. Yoshida T, Hayashi N, Nishimura S, Itoh T, Kawahara K, Okita K, Okazaki Y, Takemoto T: Mechanism of action of ethanolamine oleate used in injection sclerotherapy with special emphasis on the bronze varices. J Gastroenterol Hepatol. 1989;4 Suppl 1:173-5. [PubMed:2519043 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
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:
67791.53 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase 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 Da
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 ]
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Drug created on August 24, 2008 14:08 / Updated on August 17, 2016 12:24