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    Ethanolamine Oleate

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    RELATED EXCIPIENT COMPANIES

    EXCIPIENTS BY APPLICATIONS

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    2D Structure
    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

    2D Structure

    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 Weight 343.5 g/mol
    Molecular Formula C20H41NO3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count16
    Exact Mass343.30864417 g/mol
    Monoisotopic Mass343.30864417 g/mol
    Topological Polar Surface Area83.6 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity244
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameEthamolin
    PubMed HealthEthanolamine (Injection)
    Drug ClassesSclerosing Agent
    Drug LabelETHAMOLIN (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 IngredientEthanolamine oleate
    Dosage FormInjectable
    RouteInjection
    Strength50mg/ml
    Market StatusPrescription
    CompanyQol Medcl

    2 of 2  
    Drug NameEthamolin
    PubMed HealthEthanolamine (Injection)
    Drug ClassesSclerosing Agent
    Drug LabelETHAMOLIN (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 IngredientEthanolamine oleate
    Dosage FormInjectable
    RouteInjection
    Strength50mg/ml
    Market StatusPrescription
    CompanyQol 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.