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    Technical details about IBUTILIDE FUMARATE, learn more about the structure, uses, toxicity, action, side effects and more

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    IBUTILIDE FUMARATE

    APIs // Active Pharmaceutical Ingredients

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    DOSSIERs // Finished Dosage Forms

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    2D Structure
    1. Also known as: 122647-32-9, Corvert, Ibutilide hemifumarate, Ibutilide fumarate [usan], Ibutilide hemifumarate salt, U-70226e
    Molecular Formula
    C44H76N4O10S2
    Molecular Weight
    885.2  g/mol
    InChI Key
    PCIOHQNIRPWFMV-WXXKFALUSA-N
    FDA UNII
    9L5X4M5L6I
    Ibutilide Fumarate is the fumarate salt form of ibutilide, a class III antiarrhythmic agent. Ibutilide exerts its effect by activating a slow, inward, predominately sodium current rather than by blocking outward potassium currents. This results in prolongation of atrial and ventricular action potential duration and refractory periods. Ibutilide slightly decreases the sinus rate and atrioventricular (AV) conduction and produces a dose-related prolongation of the QT interval. (NCI05)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-but-2-enedioic acid;N-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide
    2.1.2 InChI
    InChI=1S/2C20H36N2O3S.C4H4O4/c2*1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25;5-3(6)1-2-4(7)8/h2*12-15,20-21,23H,4-11,16-17H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+
    2.1.3 InChI Key
    PCIOHQNIRPWFMV-WXXKFALUSA-N
    2.1.4 Canonical SMILES
    CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.C(=C/C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    9L5X4M5L6I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Corvert

    2. Ibutilide

    3. Ibutilide, (+)-isomer

    4. Ibutilide, (+-)-isomer

    5. Ibutilide, (-)-isomer

    6. Ibutilide, Fumarate Salt (2:1), (+)-isomer

    7. Ibutilide, Fumarate Salt (2:1), (+-)-isomer

    8. N-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide

    9. U-70226e

    10. U-82208e

    11. U-82209e

    12. U82208e

    13. U82209e

    2.3.2 Depositor-Supplied Synonyms

    1. 122647-32-9

    2. Corvert

    3. Ibutilide Hemifumarate

    4. Ibutilide Fumarate [usan]

    5. Ibutilide Hemifumarate Salt

    6. U-70226e

    7. 9l5x4m5l6i

    8. U70226e

    9. (e)-but-2-enedioic Acid;n-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide

    10. N-(4-(4-(ethyl(heptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide Hemifumarate

    11. 1807940-66-4

    12. Ncgc00181771-01

    13. Unii-9l5x4m5l6i

    14. U 70226e

    15. Corvert Fumarate

    16. Hsdb 7926

    17. Corvert (tn)

    18. Mfcd01715410

    19. Ibutilide Fumarate (usp)

    20. (+-)-4'-(4-(ethylheptylamino)-1-hydroxybutyl)methanesulfoanilide (e)-2-butenedioate (2:1)

    21. (+-)-4'-(4-(ethylheptylamino)-1-hydroxybutyl)methanesulfonanilide Fumarate (2:1) (salt)

    22. (+-)-n-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide (e)-butenedioate

    23. Dsstox_cid_28578

    24. Dsstox_rid_82849

    25. Dsstox_gsid_48652

    26. Schembl42073

    27. Chebi:5857

    28. Ibutilide Fumarate [mi]

    29. Chembl2355456

    30. Dtxsid8048652

    31. Hms3714i11

    32. Hms3884n07

    33. Ibutilide Fumarate [vandf]

    34. Ibutilide Fumarate [mart.]

    35. Bcp13494

    36. Ibutilide Fumarate [usp-rs]

    37. Ibutilide Fumarate [who-dd]

    38. Tox21_113006

    39. S2118

    40. Akos015896070

    41. Ccg-220685

    42. Ibutilide Fumarate [orange Book]

    43. As-15378

    44. Ibutilide Fumarate [usp Monograph]

    45. Methanesulfonamide, N-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)-, (+-)-, (e)-2-butenedioate (2:1) (salt)

    46. Cas-122647-32-9

    47. Ibutilide Hemifumarate Salt, >=98% (hplc)

    48. Sw220114-1

    49. D00648

    50. 647i329

    51. A804940

    52. Q27272695

    53. (+/-)-n-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide Hemifumarate

    54. Bis(n-(4-(4-(ethyl(heptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide) Fumarate

    55. (+/-)-4'-(4-(ethylheptylamino)-1-hydroxybutyl)methanesulfonanilide Fumarate (2:1) (salt)

    56. Bis(n-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide), But-2-enedioic Acid

    57. Bis(n-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide),but-2-enedioicacid

    58. Ibutilide Fumarate, United States Pharmacopeia (usp) Reference Standard, Monograph Mol Wt. 885.23 ([(c20h36n2o3s)2 . C4h4o4])

    59. Methanesulfonamide, N-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)-, (+/-)-, (e)-2-butenedioate (2:1) (salt)

    60. N-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide (e)-2-butenedioate (2:1 Salt)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 885.2 g/mol
    Molecular Formula C44H76N4O10S2
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count30
    Exact Mass884.50028698 g/mol
    Monoisotopic Mass884.50028698 g/mol
    Topological Polar Surface Area231 Ų
    Heavy Atom Count60
    Formal Charge0
    Complexity561
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameCorvert
    Drug LabelCORVERT Injection (ibutilide fumarate injection) is an antiarrhythmic drug with predominantly class III (cardiac action potential prolongation) properties according to the Vaughan Williams Classification. Each milliliter of CORVERT Injection contains...
    Active IngredientIbutilide fumarate
    Dosage FormInjectable
    RouteInjection
    Strength0.1mg/ml
    Market StatusPrescription
    CompanyPharmacia And Upjohn

    2 of 4  
    Drug NameIbutilide fumarate
    PubMed HealthIbutilide (Injection)
    Drug ClassesAntiarrhythmic, Group III
    Drug LabelCORVERT Injection (ibutilide fumarate injection) is an antiarrhythmic drug with predominantly class III (cardiac action potential prolongation) properties according to the Vaughan Williams Classification. Each milliliter of CORVERT Injection contains...
    Active IngredientIbutilide fumarate
    Dosage FormInjectable
    RouteInjection
    Strength0.1mg/ml
    Market StatusPrescription
    CompanyMylan Institutional; Luitpold

    3 of 4  
    Drug NameCorvert
    Drug LabelCORVERT Injection (ibutilide fumarate injection) is an antiarrhythmic drug with predominantly class III (cardiac action potential prolongation) properties according to the Vaughan Williams Classification. Each milliliter of CORVERT Injection contains...
    Active IngredientIbutilide fumarate
    Dosage FormInjectable
    RouteInjection
    Strength0.1mg/ml
    Market StatusPrescription
    CompanyPharmacia And Upjohn

    4 of 4  
    Drug NameIbutilide fumarate
    PubMed HealthIbutilide (Injection)
    Drug ClassesAntiarrhythmic, Group III
    Drug LabelCORVERT Injection (ibutilide fumarate injection) is an antiarrhythmic drug with predominantly class III (cardiac action potential prolongation) properties according to the Vaughan Williams Classification. Each milliliter of CORVERT Injection contains...
    Active IngredientIbutilide fumarate
    Dosage FormInjectable
    RouteInjection
    Strength0.1mg/ml
    Market StatusPrescription
    CompanyMylan Institutional; Luitpold

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Arrhythmia Agents

    Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Antiarrhythmic [EPC]
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