ETHANOLAMINE OLEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H34O2.C2H7NO
Molecular Weight	343.5444
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=KGWDUNBJIMUFAP-KVVVOXFISA-N

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-;

HIDE SMILES / InChI

Molecular Formula	C18H34O2
Molecular Weight	282.4614
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C2H7NO
Molecular Weight	61.0831
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Ethanolamine oleate is a salt of ethanolamine, a basic substance, and oleic acid. It is marketed under a trade name of Ethamoline as a sclerotic agent for the treatment of patients with esophageal varices that have recently bled, to prevent rebleeding. In vitro studies revealed that ethanolamine oleate inhibits fibrin clot formation because of the Ca2+-chelating ability of its constituent ethanolamine. Nevertheless, from in vivo studies it was suggested that intravascular injection of ethamoline activates the local coagulation system. The activation may be accelerated by an acute inflammatory process provoked by oleate, which is supported by such clinical manifestations as mild fever, retrosternal pain leukocytosis and an increase in plasma fibrinogen level.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Complement and coagulation cascades 1	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Esophageal varices 1	Primary		Approved 8,429	ETHAMOLIN
Idiopathic achalasia 1	Primary		Not Provided 504	Unknown

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ABI Chem	AC1NR05J
AN PharmaTech	AN-19880
BLD Pharm	BD01180723	http://www.bldpharm.com/products/2272-11-9.html
BioSynth	W-109765	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/W-109765.html
ChemMol	49412785	http://www.chemmol.com/chemmol/49412785.html

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PubMed

Show entries

Title	Date	PubMed
A double-blind randomized controlled trial comparing sodium tetradecyl sulphate and ethanolamine oleate in the sclerotherapy of bleeding oesophageal varices.	1993 Oct	8287811

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Patents

Sample Use Guides

In Vivo Use Guide

The usual intravenous dose is 1.5 to 5.0 mL per varix. The maximum dose per treatment session should not exceed 20 mL. Patients with significant liver dysfunction (Child Class C) or concomitant cardiopulmonary disease should usually receive less than the recommended maximum dose.

Route of Administration: Oral

In Vitro Use Guide

The effect of ethanolamine oleate (EO) and its constituents on blood coagulation was studied by means of recalcification clotting time (RCT) and FPA formation. RCT was performed using either fresh citrated whole blood or pooled plasma as substrates. The clotting end point of whole blood RCT and plasma RCT was recorded by the manual hook method and automated Clotek system, respectively. For determination of FPA formed in vitro, 250 pl fresh citrated blood was incubated with 50 ul EO or its constituent in a siliconized glass tube at 37°C for 1 min and the reaction was started by addition of 100 uL 15 mM CaCI2. At designated times, the reaction was terminated by addition of 100 uL 100 mM EDTA and 500 uL of chilled ethanol. And the supernatant of the mixture was subjected to the radioimmunoassay.