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

Structure Search

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

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2519043 | https://www.drugs.com/pro/ethamolin.html

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 Target ID: map04610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2519043	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Esophageal varices 1 Sources: https://www.drugs.com/pro/ethamolin.html	Primary		Approved 8583	ETHAMOLIN Approved Use Ethamolin Injection is indicated for the treatment of patients with esophageal varices that have recently bled, to prevent rebleeding. Ethamolin is not indicated for the treatment of patients with esophageal varices that have not bled. There is no evidence that treatment of this population decreases the likelihood of bleeding. Sclerotherapy with Ethamolin has no beneficial effect upon portal hypertension, the cause of esophageal varices, so that recanalization and collateralization may occur, necessitating reinjection. Launch Date 1988
Idiopathic achalasia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21971376	Primary		Not Provided 511	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/7875322/	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1NR05J
AN PharmaTech	AN-19880
BioSynth	W-109765	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/W-109765.html
BLD Pharm	BD01180723	http://www.bldpharm.com/products/2272-11-9.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0000631
ChemMol	49412785	http://www.chemmol.com/chemmol/49412785.html
ChemMol	99056090	http://www.chemmol.com/chemmol/99056090.html
eNovation Chemicals	D676377	https://enovationchem.com/ProductDetails.asp?ProductID=D676377
MuseChem	I008131	https://www.musechem.com/product/I008131.html
NovoSeek	5282489
PubChem	5282489	https://pubchem.ncbi.nlm.nih.gov/compound/5282489
Smolecule	S536010	http://www.smolecule.com/products/s536010
THE BioTek	bt-275061	https://www.thebiotek.com/product/inhibitors/bt-275061
Wikidata	Q6901567

PubMed

Title	Date	PubMed
Ethanolamine oleate in resistant idiopathic achalasia: a novel therapy.	2011-11	21971376
A double-blind randomized controlled trial comparing sodium tetradecyl sulphate and ethanolamine oleate in the sclerotherapy of bleeding oesophageal varices.	1993-10	8287811
Mechanism of action of ethanolamine oleate used in injection sclerotherapy with special emphasis on the bronze varices.	1989	2519043
FATTY ACID SOLUTIONS FOR THE INJECTION TREATMENT OF VARICOSE VEINS: EVALUATION OF FOUR NEW SOLUTIONS.	1937-04	17856963

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:43:12 GMT 2025` Edited by `admin` on `Wed Apr 02 09:43:12 GMT 2025`
Record UNII	U4RY8MRX7C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHANOLAMINE OLEATE

Official Name

English

MONOETHANOLAMINE OLEATE

Preferred Name

English

ETHANOLAMINE OLEATE [VANDF]

Common Name

English

OLDAMIN

Brand Name

English

Monoethanolamine oleate [WHO-DD]

Common Name

English

MONOETHANOLAMINE OLEATE [MART.]

Common Name

English

9-OCTADECENOIC ACID (Z)-, COMPOUND WITH 2-AMINOETHANOL (1:1)

Common Name

English

ETHANOLAMINE OLEATE [MI]

Common Name

English

ETHANOLAMINE OLEATE [ORANGE BOOK]

Common Name

English

9-OCTADECENOIC ACID (Z)-, COMPD WITH 2-AMINOETHANOL (1:1)

Common Name

English

MONOETHANOLAMINE OLEATE [JAN]

Common Name

English

monoethanolamine oleate [INN]

Common Name

English

NSC-760382

Code

English

ETHANOLAMINE OLEATE [USAN]

Common Name

English

Oleic acid compound with 2-aminoethanol (1:1)

Systematic Name

English

ETHAMOLIN

Brand Name

English

Classification Tree Code System Code

WHO-ATC

C05BB01