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Ibutilide

Ibutilide

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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

Ibutilide

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 Formula	C₄₄H₇₆N₄O₁₀S₂
Molecular Weight	885.2 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	30
Exact Mass	884.50028698 g/mol
Monoisotopic Mass	884.50028698 g/mol
Topological Polar Surface Area	231 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	561
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Corvert
Drug Label	CORVERT 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 Ingredient	Ibutilide fumarate
Dosage Form	Injectable
Route	Injection
Strength	0.1mg/ml
Market Status	Prescription
Company	Pharmacia And Upjohn

2 of 4
Drug Name	Ibutilide fumarate
PubMed Health	Ibutilide (Injection)
Drug Classes	Antiarrhythmic, Group III
Drug Label	CORVERT 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 Ingredient	Ibutilide fumarate
Dosage Form	Injectable
Route	Injection
Strength	0.1mg/ml
Market Status	Prescription
Company	Mylan Institutional; Luitpold

3 of 4
Drug Name	Corvert
Drug Label	CORVERT 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 Ingredient	Ibutilide fumarate
Dosage Form	Injectable
Route	Injection
Strength	0.1mg/ml
Market Status	Prescription
Company	Pharmacia And Upjohn

4 of 4
Drug Name	Ibutilide fumarate
PubMed Health	Ibutilide (Injection)
Drug Classes	Antiarrhythmic, Group III
Drug Label	CORVERT 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 Ingredient	Ibutilide fumarate
Dosage Form	Injectable
Route	Injection
Strength	0.1mg/ml
Market Status	Prescription
Company	Mylan 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]