Identification
- Summary
Ethanolamine oleate is a mild sclerosing agent used in the treatment of esophageal varices with recent bleeding episodes.
- Brand Names
- Ethamolin
- Generic Name
- Ethanolamine oleate
- DrugBank Accession Number
- DB06689
- Background
Ethanolamine 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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ethanolamine oleate (DB06689)
- Weight
- Average: 343.5444
Monoisotopic: 343.308644183 - Chemical Formula
- C20H41NO3
- Synonyms
- Ethamolin
- Ethanolamine oleate
- Monoethanolamine oleate
- Monoethanolamini oleas
- Oldamin
- Oleate de monoethanolamine
- Oleato de monoetanolaminio
- External IDs
- FO-611
Pharmacology
- Indication
For the treatment of patients with esophageal varices that have recently bled, to prevent rebleeding.
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.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Esophageal varices •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
When 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 action
The 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.
Target Actions Organism UCalcium ions chelatorHumans UCoagulation factor XII activatorHumans - Absorption
After 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 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. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.No interactions found.
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Ethanolamine unknown 5KV86114PT 141-43-5 HZAXFHJVJLSVMW-UHFFFAOYSA-N - International/Other Brands
- Monolate / Moramin / Neosclerol / Oldamin / Varicetin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ethamolin Injection, solution 50 mg/1mL Intravenous QOL Medical, LLC. 1998-12-22 Not applicable US 
Ethanolamine Oleate Inj 50mg/ml Liquid 50 mg / mL Intravenous Block Drug Company (Canada) Ltd. 1992-12-31 2001-04-17 Canada 
Categories
- ATC Codes
- C05BB01 — Monoethanolamine oleate
- Drug Categories
- Antivaricose Therapy
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Fatty Acids
- Fatty Acids, Monounsaturated
- Fatty Acids, Unsaturated
- Lipids
- Pharmaceutical Preparations
- Pharmaceutical Solutions
- Sclerosing Agents for Local Injection
- Sclerosing Solutions
- Solutions
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- 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
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Not Available
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- U4RY8MRX7C
- CAS number
- 2272-11-9
- InChI Key
- 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
References
- General References
- NOORDIJK JA: [Monoethanolamine oleate]. Ned Tijdschr Geneeskd. 1950 Apr 22;94(16):1110-1. [Article]
- Howard ER, Stamatakis JD, Mowat AP: Management of esophageal varices in children by injection sclerotherapy. J Pediatr Surg. 1984 Feb;19(1):2-5. [Article]
- PACCA ML: [Antihyaluronidase activity of monoethanolamine oleate]. Boll Soc Ital Biol Sper. 1951 Mar-Apr;27(4):576-9. [Article]
- 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. [Article]
- VOIGT J: [Allergy to varex (monoethanolamine oleate)]. Ugeskr Laeger. 1954 Mar 25;116(12):452-7. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015638
- KEGG Drug
- D02276
- PubChem Compound
- 5282489
- PubChem Substance
- 99443246
- ChemSpider
- 4445632
- 24460
- ChEBI
- 178699
- ChEMBL
- CHEMBL3989529
- PharmGKB
- PA164746758
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Monoethanolamine_oleate
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Unknown Status Treatment Oesophageal varices haemorrhage 1 1, 2 Withdrawn Supportive Care Chronic Myeloproliferative Disorders / Infection / Leukemias / Lymphoma / Lymphoproliferative Disorders / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndrome / Myeloproliferative/Myelodysplastic Neoplasm / Unspecified Adult Solid Tumor, Protocol Specific 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Ben Venue Laboratories Inc.
- QOL Medical
- Dosage Forms
Form Route Strength Injection, solution Intravenous 50 mg/1mL Liquid Intravenous 50 mg / mL - Prices
Unit description Cost Unit Ethamolin 5% ampul 86.62USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000121 mg/mL ALOGPS logP 7.68 ALOGPS logP 6.78 Chemaxon logS -6.4 ALOGPS pKa (Strongest Acidic) 4.99 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 87.4 m3·mol-1 Chemaxon Polarizability 37.09 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9805 Blood Brain Barrier - 0.6473 Caco-2 permeable - 0.5672 P-glycoprotein substrate Substrate 0.6703 P-glycoprotein inhibitor I Non-inhibitor 0.959 P-glycoprotein inhibitor II Non-inhibitor 0.9592 Renal organic cation transporter Non-inhibitor 0.8873 CYP450 2C9 substrate Non-substrate 0.853 CYP450 2D6 substrate Non-substrate 0.7411 CYP450 3A4 substrate Non-substrate 0.7548 CYP450 1A2 substrate Inhibitor 0.6639 CYP450 2C9 inhibitor Non-inhibitor 0.9248 CYP450 2D6 inhibitor Non-inhibitor 0.8421 CYP450 2C19 inhibitor Non-inhibitor 0.9104 CYP450 3A4 inhibitor Non-inhibitor 0.8594 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9496 Ames test Non AMES toxic 0.9378 Carcinogenicity Non-carcinogens 0.8135 Biodegradation Ready biodegradable 0.7487 Rat acute toxicity 1.5407 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9046 hERG inhibition (predictor II) Non-inhibitor 0.8212
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.78914 predictedDeepCCS 1.0 (2019) [M+H]+ 190.14714 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.3301 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Unknown
Chelator
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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 t...
- Gene Name
- F12
- Uniprot ID
- P00748
- Uniprot Name
- Coagulation factor XII
- Molecular Weight
- 67791.53 Da
References
- 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. [Article]
- 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. [Article]
Drug created at August 24, 2008 20:08 / Updated at February 21, 2024 02:33