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Ethanolamine Oleate_Molecular_structure_CAS_2272-11-9)
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Ethanolamine Oleate

Catalog No. DB06689 Name DrugBank
CAS Number 2272-11-9 Website http://www.ualberta.ca/
M. F. C20H41NO3 Telephone (780) 492-3111
M. W. 343.54444 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 4430

SYNONYMS

IUPAC name
(9Z)-octadec-9-enoic acid; 2-aminoethan-1-ol
IUPAC Traditional name
2-aminoethanol; oleic acid
Brand Name
Ethamolin
Oldamin
Neosclerol
Monolate
Varicetin
Moramin
Varex
Synonyms
Monoethanolamine oleate
cis-9-Octadecenoic acid, ethanolamine salt
beta-Hydroxyethylammonium oleate

DATABASE IDS

PubChem CID 5282489
PubChem SID 99443246
CAS Number 2272-11-9

PROPERTIES

DETAILS

Description (English)
Item Information
Drug Groups approved
Description 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.
Indication For the treatment of patients with esophageal varices that have recently bled, to prevent rebleeding.
Pharmacology 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.
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.
Affected Organisms
Humans and other mammals
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.
References
NOORDIJK JA: [Monoethanolamine oleate.] Ned Tijdschr Geneeskd. 1950 Apr 22;94(16):1110-1. [Pubmed]
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]
PACCA ML: [Antihyaluronidase activity of monoethanolamine oleate.] Boll Soc Ital Biol Sper. 1951 Mar-Apr;27(4):576-9. [Pubmed]
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]
VOIGT J: [Allergy to varex (monoethanolamine oleate).] Ugeskr Laeger. 1954 Mar 25;116(12):452-7. [Pubmed]
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]
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] Nippon Shokakibyo Gakkai Zasshi. 1984 Jun;81(6):1491. [Pubmed]
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]
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]
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]
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]
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]
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REFERENCES

  • 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] Nippon Shokakibyo Gakkai Zasshi. 1984 Jun;81(6):1491. Pubmed
  • 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
  • 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
  • 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
  • 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
  • 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
  • NOORDIJK JA: [Monoethanolamine oleate.] Ned Tijdschr Geneeskd. 1950 Apr 22;94(16):1110-1. Pubmed
  • 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
  • VOIGT J: [Allergy to varex (monoethanolamine oleate).] Ugeskr Laeger. 1954 Mar 25;116(12):452-7. Pubmed
  • PACCA ML: [Antihyaluronidase activity of monoethanolamine oleate.] Boll Soc Ital Biol Sper. 1951 Mar-Apr;27(4):576-9. Pubmed
  • 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
  • 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