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2272-11-9 molecular structure
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(9Z)-octadec-9-enoic acid; 2-aminoethan-1-ol

ChemBase ID: 4430
Molecular Formular: C20H41NO3
Molecular Mass: 343.54444
Monoisotopic Mass: 343.30864418
SMILES and InChIs

SMILES:
C(C/C=C\CCCCCCCC)CCCCCC(=O)O.OCCN
Canonical SMILES:
CCCCCCCC/C=C\CCCCCCCC(=O)O.NCCO
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-;
InChIKey:
KGWDUNBJIMUFAP-KVVVOXFISA-N

Cite this record

CBID:4430 http://www.chembase.cn/molecule-4430.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
beta-Hydroxyethylammonium oleate
cis-9-Octadecenoic acid, ethanolamine salt
Ethanolamine Oleate
CAS Number
2272-11-9
PubChem SID
99443246
160967862
PubChem CID
5282489

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 4.9881673  H Acceptors
H Donor LogD (pH = 5.5) 6.155865 
LogD (pH = 7.4) 4.4022083  Log P 6.783798 
Molar Refractivity 87.4022 cm3 Polarizability 34.16541 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds 16 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Bioassay(PubChem)

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB06689 external link
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]
External Links
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REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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