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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 of ETHANOLAMINE OLEATE

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

5.9866559E11
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
FATTY ACID SOLUTIONS FOR THE INJECTION TREATMENT OF VARICOSE VEINS: EVALUATION OF FOUR NEW SOLUTIONS.
1937 Apr
Mechanism of action of ethanolamine oleate used in injection sclerotherapy with special emphasis on the bronze varices.
1989
A double-blind randomized controlled trial comparing sodium tetradecyl sulphate and ethanolamine oleate in the sclerotherapy of bleeding oesophageal varices.
1993 Oct
Ethanolamine oleate in resistant idiopathic achalasia: a novel therapy.
2011 Nov
Patents

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 Thu Jul 06 23:12:12 UTC 2023
Edited
by admin
on Thu Jul 06 23:12:13 UTC 2023
Record UNII
U4RY8MRX7C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHANOLAMINE OLEATE
MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official 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
MONOETHANOLAMINE OLEATE
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
ETHAMOLIN
Brand Name English
Classification Tree Code System Code
WHO-ATC C05BB01
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
FDA ORPHAN DRUG 1484
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
WHO-VATC QC05BB01
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
NCI_THESAURUS C78275
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
Code System Code Type Description
MESH
C033343
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
DRUG CENTRAL
4086
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
RXCUI
24460
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY RxNorm
FDA UNII
U4RY8MRX7C
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
NCI_THESAURUS
C61757
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
ECHA (EC/EINECS)
218-878-0
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
PUBCHEM
5282489
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
SMS_ID
100000080380
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
INN
4152
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
EVMPD
SUB09050MIG
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
NSC
760382
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL104943
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200394
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
DAILYMED
U4RY8MRX7C
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
USAN
W-126
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
CAS
2272-11-9
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
MERCK INDEX
M5052
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID8023008
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
WIKIPEDIA
Ethanolamine oleate
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
DRUG BANK
DB06689
Created by admin on Thu Jul 06 23:12:13 UTC 2023 , Edited by admin on Thu Jul 06 23:12:13 UTC 2023
PRIMARY
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