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Ethanolamine Oleate

Synopsis, Chemistry

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Also known as: Ethamolin, Monoethanolamine oleate, Oldamin, 2272-11-9, Beta-hydroxyethylammonium oleate, Oleic acid (ethanolamine)

Molecular Formula

C₂₀H₄₁NO₃

Molecular Weight

343.5 g/mol

InChI Key

KGWDUNBJIMUFAP-KVVVOXFISA-N

FDA UNII

U4RY8MRX7C

Ethanolamine Oleate is a synthetic preparation of oleic acid and ethanolamine, a first generation monoethanolamine with sclerotherapeutic activity. Ethanolamine oleate causes an acute, dose-related inflammatory reaction of the intimal endothelium of the vein. This leads to scarring at the inner wall of the veins and possible occlusion of the veins. The oleic acid component may also transiently activate coagulation and fibrinolytic systems through the release of tissue factor and activation of Hageman factor.

1 2D Structure

Ethanolamine Oleate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-aminoethanol;(Z)-octadec-9-enoic acid

2.1.2 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-;

2.1.3 InChI Key

KGWDUNBJIMUFAP-KVVVOXFISA-N

2.1.4 Canonical SMILES

CCCCCCCCC=CCCCCCCCC(=O)O.C(CO)N

2.1.5 Isomeric SMILES

CCCCCCCC/C=C\CCCCCCCC(=O)O.C(CO)N

2.2 Other Identifiers

2.2.1 UNII

U4RY8MRX7C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ethamolin

2. Oleic Acid, 2-aminoethyl Ester

3. Monoethanolamine Oleate

2.3.2 Depositor-Supplied Synonyms

1. Ethamolin

2. Monoethanolamine Oleate

3. Oldamin

4. 2272-11-9

5. Beta-hydroxyethylammonium Oleate

6. Oleic Acid (ethanolamine)

7. U4ry8mrx7c

8. 2-aminoethan-1-ol Oleate

9. Ethanolamine Oleate [usan]

10. Monoethanolamine Oleate [inn]

11. Nsc-760382

12. 2-aminoethanol;(z)-octadec-9-enoic Acid

13. Ethanolamine Oleate (usan)

14. Oleic Acid Compound With 2-aminoethanol (1:1)

15. Monoethanolamine Oleate (jan)

16. Neosclerol

17. Monolate

18. Moramin

19. Varicetin

20. Varex

21. 9-octadecenoic Acid (z)-, Compound With 2-aminoethanol (1:1)

22. Monoethanolamine Oleate [jan]

23. Ethamolin (tn)

24. Esclerosina

25. Antivariz

26. Phlebocid

27. Thanomin

28. Tindanol

29. Neo-varicane

30. Ethanolamine-oleate

31. Oldamin (tn)

32. Monoethanolamini Oleas

33. Monoaethanolamini Oleas

34. Monoetanolammina Oleato

35. Cis-9-octadecenoic Acid, Ethanolamine Salt

36. Unii-u4ry8mrx7c

37. Oleate De Monoethanolamine

38. Oleato De Monoetanolaminio

39. Oleic Acid Monoethanolamine

40. Oleic Acid Ethanolamine Salt

41. Oleic Acid, Ethanolamine Salt

42. Schembl146090

43. Ccris 3324

44. Monoetanolammina Oleato [dcit]

45. Oleic Acid Monoethanolamine Salt

46. Chembl3989529

47. Dtxsid8023008

48. Ethanolamine Oleate [mi]

49. Oleic Acid, 2-aminoethanol Salt

50. Oleic Acid, Monoethanolamine Salt

51. Chebi:178699

52. 9-octadecenoic Acid (z)-, Compd. With 2-aminoethanol (1:1)

53. Ethanolamine Oleate [vandf]

54. Hy-b2096

55. Monoethanolamini Oleas [inn-latin]

56. Einecs 218-878-0

57. Fo-611

58. Db06689

59. Monoethanolamine Oleate [mart.]

60. Nsc 760382

61. Monoethanolamine Oleate [who-dd]

62. Ethanolamine Oleate [orange Book]

63. Oleate De Monoethanolamine [inn-french]

64. Oleato De Monoetanolaminio [inn-spanish]

65. Cs-0017525

66. D02276

67. Ec 218-878-0

68. Oleic Acid, Compd. With 2-aminoethanol (1:1)

69. W-109765

70. (9z)-octadec-9-enoic Acid - 2-aminoethanol (1:1)

71. 9-octadecenoic Acid (9z)-, Compd. With 2-aminoethanol (1:1)

72. 9-octadecenoic Acid (z)-, Compd With 2-aminoethanol (1:1)

2.4 Create Date

2005-10-11

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₄₁NO₃
Molecular Weight	343.5 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	16
Exact Mass	343.30864417 g/mol
Monoisotopic Mass	343.30864417 g/mol
Topological Polar Surface Area	83.6 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	244
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Ethamolin
PubMed Health	Ethanolamine (Injection)
Drug Classes	Sclerosing Agent
Drug Label	ETHAMOLIN (Ethanolamine Oleate) Injection is a mild sclerosing agent. Chemically it is C17H33COOHNH2CH2CH2OH. It has the following structure:The empirical formula is C20H41NO3, representing a molecular weight of 343.55.ETHAMOLIN Injection consis...
Active Ingredient	Ethanolamine oleate
Dosage Form	Injectable
Route	Injection
Strength	50mg/ml
Market Status	Prescription
Company	Qol Medcl

2 of 2
Drug Name	Ethamolin
PubMed Health	Ethanolamine (Injection)
Drug Classes	Sclerosing Agent
Drug Label	ETHAMOLIN (Ethanolamine Oleate) Injection is a mild sclerosing agent. Chemically it is C17H33COOHNH2CH2CH2OH. It has the following structure:The empirical formula is C20H41NO3, representing a molecular weight of 343.55.ETHAMOLIN Injection consis...
Active Ingredient	Ethanolamine oleate
Dosage Form	Injectable
Route	Injection
Strength	50mg/ml
Market Status	Prescription
Company	Qol Medcl

4.2 Drug Indication

For the treatment of patients with esophageal varices that have recently bled, to prevent rebleeding.

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Sclerosing Solutions

Chemical agents injected into blood vessels and lymphatic sinuses to shrink or cause localized THROMBOSIS; FIBROSIS, and obliteration of the vessels. This treatment is applied in a number of conditions such as VARICOSE VEINS; HEMORRHOIDS; GASTRIC VARICES; ESOPHAGEAL VARICES; PEPTIC ULCER HEMORRHAGE. (See all compounds classified as Sclerosing Solutions.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Sclerosing Agent [EPC]; Vascular Sclerosing Activity [PE]; Sclerosing Activity [MoA]

5.4 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

C05B - Antivaricose therapy

C05BB - Sclerosing agents for local injection

C05BB01 - Monoethanolamine oleate

5.5 Absorption, Distribution and Excretion

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.

5.6 Mechanism of Action

The oleic acid component of ethanolamine oleate is responsible for the inflammatory response, and may also activate coagulation in vivo by release of tissue factor and activation of Hageman factor. The ethanolamine component, however, may inhibit fibrin clot formation by chelating calcium, so that a procoagulant action of ethanolamine oleate has not been demonstrated.