Description
Ibutilide fumarate · CAS 122647-32-9 · C20H36N2O3S. UNII 2436VX1U9B. Solubility: 100; Solubility: 4.73e-03 g/L; LogP: 4.6.
Identification
| CAS Registry Number | 122647-32-9 |
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| PubChem CID | 60753 |
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| Molecular formula | C20H36N2O3S |
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| IUPAC name | N-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide |
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| UNII (FDA) | 2436VX1U9B |
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Computed Descriptors
| Molecular Weight | 384.6 |
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| XLogP3 | 4 |
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| Hydrogen Bond Donor Count | 2 |
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| Hydrogen Bond Acceptor Count | 5 |
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| Rotatable Bond Count | 14 |
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| Exact Mass | 384.24466419 |
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| Monoisotopic Mass | 384.24466419 |
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| Topological Polar Surface Area | 78 |
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| Heavy Atom Count | 26 |
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| Formal Charge | 0 |
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Physical & Chemical Properties
| Solubility | 100 |
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| Solubility | 4.73e-03 g/L |
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| LogP | 4.6 |
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Physical description & handling notes
- Solid
- MW: 885.23. Crystals from acetone, mp 117-119 °C.; UV max (95% ethanol): 228, 267 nm (epsilon 16670, 894); solubility: (mg/mL): aqueous >100 (pH less than or equal to 7) /Ibutilide fumarate/
- Parenteral: Injection, for IV infusion: 1 mg (0.1 mg/mL), Covert (Pfizer). /Ibutilide fumarate/
Documented Uses
- The synthesis starts with a Friedel-Crafts acylation of methanesulfonanilide with succinic anhydride in presence of AlCl3 yielding 4-[(methylsulfonyl)amino]-gamma-oxobenzenebutanoic acid, which is treated with N-ethylheptylamine and dicyclohexylcarbodiimide (DCC) in DMF to give the corresponding amide. Reduction with LiAlH4 in THF in the last step provides the desired drug substance.
- Indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm.
- Ibutilide is a class III antiarrhythmic medication approved by the US Food and Drug Administration (FDA) for converting acute atrial flutter and atrial fibrillation to normal sinus rhythm. Research indicates ibutilide's greater efficacy in treating atrial flutter compared to atrial fibrillation.
- Ibutilide fumarate injection is indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm. Patients with atrial arrhythmias of longer duration are less likely to respond to ibutilide fumarate injection. The effectiveness of ibutilide has not been determined in patients with arrhythmias of more than 90 days in duration. /Included in US product label/
- Ibutilide is administered as a rapid infusion (1 mg over 10 minutes) for the immediate conversion of atrial fibrillation or flutter to sinus rhythm. The drug's efficacy rate is higher in patients with atrial flutter (50-70%) than in those with atrial fibrillation (30-50%). In atrial fibrillation, the conversion rate is lower in those in whom the arrhythmia has been present for weeks or months compared with those in whom it has been present for days.
- Patients with chronic atrial fibrillation have a strong tendency to revert after conversion to sinus rhythm and treatments to maintain sinus rhythm carry risks. Patients to be treated with ibutilide fumarate injection, therefore, should be carefully selected such that the expected benefits of maintaining sinus rhythm outweigh the immediate risks of ibutilide fumarate injection, and the risks of maintenance therapy, and are likely to offer an advantage compared with alternative management.
Synonyms
Ibutilide; 122647-31-8; Ibutilida; Ibutilidum; n-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide; N-(4-(4-(ethyl(heptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide; N-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide; 2436VX1U9B; DTXSID20861271; N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide; N-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide; RefChem:56518; C01BD05; DTXCID30197270; Ibutilidum [INN-Latin]; Ibutilida [INN-Spanish]
Frequently Asked Questions
What are the CAS number and molecular formula of Ibutilide fumarate?
CAS 122647-32-9; molecular formula C20H36N2O3S; molecular weight — g/mol.
What other names is Ibutilide fumarate known by?
Ibutilide, 122647-31-8, Ibutilida, Ibutilidum, n-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide, N-(4-(4-(ethyl(heptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide.
What are the key physical properties of Ibutilide fumarate?
Solubility: 100; Solubility: 4.73e-03 g/L; LogP: 4.6.
Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.
