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IBUTILIDE

Product Name
IBUTILIDE
CAS No.
122647-31-8
Chemical Name
IBUTILIDE
Synonyms
Corvert;U-70226E;IBUTIBIDE;IBUTILIDE;Ibutilida;Ibutilidum;Rosuvastatin-d;Unii-2436vx1U9b;IBUTILIDE USP/EP/BP;122647-32-9 (Fumarate)
CBNumber
CB0698355
Molecular Formula
C20H36N2O3S
Formula Weight
384.58
MOL File
122647-31-8.mol
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IBUTILIDE Property

Boiling point:
522.4±60.0 °C(Predicted)
Density 
1.099±0.06 g/cm3(Predicted)
pka
8.54±0.10(Predicted)
CAS DataBase Reference
122647-31-8
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0006228
Product name
IBUTILIDE
Purity
95.00%
Packaging
25MG
Price
$267.75
Updated
2021/12/16
AHH
Product number
MT-52774
Product name
Ibutilide
Purity
98%
Packaging
0.1g
Price
$610
Updated
2021/12/16
AvaChem
Product number
2455B
Product name
Ibutilide
Packaging
1g
Price
$850
Updated
2021/12/16
AvaChem
Product number
2455B
Product name
Ibutilide
Packaging
10mg
Price
$55
Updated
2021/12/16
AvaChem
Product number
2455B
Product name
Ibutilide
Packaging
100mg
Price
$175
Updated
2021/12/16
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IBUTILIDE Chemical Properties,Usage,Production

Originator

Corvert,Pharmacia and Upjohn,USA

Uses

Cardiac depressant (anti-arrhythmic).

Definition

ChEBI: Ibutilide is an organic amino compound and a member of benzenes.

Manufacturing Process

A mechanically stirred solution of aniline (139.7 g, 1.5 mole) in pyridine (2 L), under N2 is cooled in an ice bath. Methanesulfonyl chloride (171.8 g, 1.5 mole) is added dropwise to this solution while the temperature is maintained at 15°-20°C, which results in a red-orange color change in the reaction mixture. After the addition is complete the ice bath is removed and the reaction is allowed to continue at room temperature. The reaction is complete after 2.5 h. The reaction mixture is concentrated in vacuo and the residue is combined with 700 ml of water which results in crystallization of a dark red material.
This material is filtered and washed several times with water. The filtered material is dissolved in CH2Cl2, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue is dissolved in hot ethyl acetate, treated with Darco (decolorizing carbon) and crystallized to yield methanesulfonanilide which had a melting point: 93°-94°C.
A mechanically stirred suspension of aluminum chloride (88.0 g, 0.66 moles) and 150 ml of carbon disulfide under N2 is cooled in an ice bath. Methanesulfonanilide (30.0 g, 0.175 mol) and succinic anhydride (17.5 g, 0.175 mol) are combined and added rapidly to the cooled reaction mixture. The ice bath is removed and the mixture is stirred at room temperature for 6 h. The reaction mixture is then heated to 55°C and allowed to continue for 18 h. The reaction mixture is separated into two layers the bottom of which solidifies.
The upper layer is decanted and the remaining solid layer is decomposed with ice. The resulting suspension is filtered and the solid is washed several times with methylene chloride and dissolved in a mixture of saturated sodium bicarbonate (500 ml) and water (500 ml). This solution is acidified (pH 2) with HCl and the resulting precipitate is collected by filtration, redissolved in NaHCO3 and reprecipitated with HCl. The solid, 4-[(methylsulfonyl)amino]-γ- oxobenzenebutanoic acid, is collected by filtration. Melting point 198°-200°C.
A stirred solution of 4-[(methylsulfonyl)amino]-γ-oxobenzenebutanoic acid (12.0 g, 0.044 mol) in DMF (100 ml) under N2 is cooled in an ice bath to 5°C and treated with 1-hydroxybenzotriazole (5.94 g, 0.044 mol) and N,N'- dicyclohexylcarbodiimide (9.08 g, 0.044 mol). After 1 hour, ethylheptylamine (6.3 g, 0.044 mol) is added, after an additional 30 min the ice bath is removed and the mixture is kept at room temperature for 18 h.
The reaction mixture is filtered over a Celite filter aid and the filtrate is concentrated under vacuum. The resulting material is dissolved in CH2Cl2, washed with dilute HCl, NaHCO3 and concentrated. The residue is chromatographed over silica gel (1.25 kg) with 5% MeOH : 1% NH4OH : CH2Cl2. The N-ethyl-N-heptyl-γ-oxo-4-[(methylsulfonyl)amino]benzenebutanamide thus obtained is crystallized from EtOAc to yield 10.77 g, melting point 100°-102°C.
To a N2 covered suspension of 0.29 g (7.57 mmol) of LiAlH4 in 10 ml of THF cooled in an ice bath is added a solution of 1.0 g (2.52 mmol) of N-ethyl-Nheptyl-γ-oxo-4-[methylsulfonyl)amino]benzenebutanamide in 10 ml of THF over 6 min. The ice bath is then removed and the mixture heated at reflux for 27 h and then stirred at room temperature for 2 days. The mixture is cooled in an ice bath and there is added dropwise 10 ml of aqueous sodium potassium tartrate followed by EtOAc and H2O to keep the mixture fluid.
The aqueous fraction is extracted once with EtOAc and the combined EtOAc fractions are washed in turn with H2O and concentrated in vacuo. The residue is chromatographed on a 200 ml silica gel column (elution with 6% MeOH : CH2Cl2 containing 0.5% NH4OH) and 9.7 ml fractions were collected and treated with Et2O and aqueous NaHCO3. The organic layer is concentrated in vacuo to yield N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl] methanesulfonamide.
Preparation of fumarate (WO Patent 01/07417). To dichloromethane solution of 4-[4-N-[(Ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide is added hemimolar quantities of fumaric acid and heated to reflux until a clear solution was obtained. Upon cooling the fumarate of 4-[4-N- [(Ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide was obtained.

brand name

Inocor (Sterling Winthrop).

Therapeutic Function

Antiarrhythmic

General Description

Ibutilide, N-{4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl}methanesulfonamide (Corvert), aclass III antiarrhythmic belonging to the methanesulfonanilideclass of agents, is indicated for rapid conversion ofatrial fibrillation or atrial flutter to normal sinus rhythm.Unlike dofetilide, it is not highly specific for the delayedrectifier potassium currents (Ikr) and does have some affinityfor sodium channels.

Clinical Use

Ibutilide (Corvert) is another methanesulfonanilide derivative , but unlike sotalol, it lacks any β-adrenergic blocking activity. Like sotalol, it exhibits electrophysiologic effects characteristic of Class III. Ibutilide is used only by intravenous infusion as its fumarate salt.

IBUTILIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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IBUTILIDE Suppliers

TargetMol Chemicals Inc.
Tel
+8613564774135
Email
zijue.cai@tsbiochem.com
Country
United States
ProdList
19885
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Amfinecom Inc.
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--
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Email
sales@amfinecom.com
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United States
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AvaChem Scientific LLC
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--
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Info@avachem.com
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United States
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American Custom Chemicals Corporation
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--
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Email
sales@acccorporation.com
Country
United States
ProdList
6820
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AmplaChem, Inc.
Tel
--
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Email
info@amplacheminc.com
Country
United States
ProdList
428
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Waterstone Technology, LLC
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--
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Email
sales@waterstonetech.com
Country
United States
ProdList
6786
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2A PharmaChem USA
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Email
sales@2apharmachem.com
Country
United States
ProdList
6137
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3B Scientific Corporation
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--
Fax
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Email
sales@3bsc.com
Country
United States
ProdList
6718
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AK Scientific, Inc.
Tel
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Email
sales@aksci.com
Country
United States
ProdList
6347
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APAC Pharmaceutical, LLC
Tel
--
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Email
sales@apacpharma.com
Country
United States
ProdList
6322
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View Lastest Price from IBUTILIDE manufacturers

Career Henan Chemical Co
Product
IBUTILIDE 122647-31-8
Price
US $1.00/KG
Min. Order
1KG
Purity
98%-99.9%
Supply Ability
200KG
Release date
2020-01-07

122647-31-8, IBUTILIDERelated Search:


  • IBUTILIDE
  • IBUTIBIDE
  • (±)-N-[4-[4-(Ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide
  • Corvert
  • U-70226E
  • 122647-32-9 (Fumarate)
  • 4-(N-Ethylheptylamino)-1-(4-methylsulfonylaminophenyl)-1-butanol
  • Ibutilida
  • Ibutilida [inn-spanish]
  • Ibutilidum
  • Ibutilidum [inn-latin]
  • Unii-2436vx1U9b
  • MethanesulfonaMide, N-[4-[4-(ethylheptylaMino)-1-hydroxybutyl]phenyl]-
  • IBUTILIDE USP/EP/BP
  • Rosuvastatin-d
  • 122647-31-8
  • C20H36N2O3S