Basic information
- CAS
122647-32-9- Standard SMILES
CCCCCCCN(CC)CCCC(O)c1ccc(NS(C)(=O)=O)cc1.CCCCCCCN(CC)CCCC(O)c1ccc(NS(C)(=O)=O)cc1.O=C(O)/C=C/C(=O)O- InChIKey
PCIOHQNIRPWFMV-WXXKFALUSA-N- Molecular formula
- C44H76N4O10S2
- Average molar mass
- 885.2 g/mol
- Monoisotopic mass
- 884.50028698
Overview
Ibutilide fumarate is a member of benzenes and an organic amino compound.
Names & identifiers
- Preferred name
- Ibutilide Fumarate
- IUPAC
- (E)-but-2-enedioic acid;bis(N-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide)
- English name
- Ibutilide fumarate
- Molecular formula
- (C20H36N2O3S)2.C4H4O4
- Molecular weight
- 885.24
Names & synonyms
IBUTILIDE FUMARATE122647-32-9CorvertU-70226EDTXSID80486529L5X4M5L6IDTXCID1028578RefChem:56519Ibutilide Fumarate [USAN]MFCD017154101807940-66-4Ibutilide (fumarate)
Show more names
D00648Corvert (tn)Corvert FumarateIBUTILIDE FUMRTATEIbutibide FumarateIbulitide fumarateIbutilide 1/2FumarateIbutilide hemifumarateIbutilideHemifumarate>
Methanesulfonamide, N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]-, (2E)-2-butenedioate (2:1)(E)-but-2-enedioic acid;N-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamidebis(N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide); but-2-enedioic acidIbutilide Fumarate-d5U70226EN-(4-(4-(ethyl(heptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide hemifumarateBis(N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide), but-2-enedioic acidC44H76N4O10S2
Database identifiers
- CAS
122647-32-9
Properties
Computed structural properties
- Topological polar surface area
- 231 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 30
- Heavy atoms
- 60
- Formal charge
- 0
- Complexity
- 561
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 112 · 112-117C
- RTECS
- 475700 · PB0475700
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: >20mg/mL
- form
- solid
- color
- off-white to tan
- Water Solubility
- 2 O: · H2O: >20mg/mL
- λmax
- 267 nm · 267nm(EtOH)(lit.)
- Merck
- 14 · 14,4883
- InChIKey
- PCIOHQNIRPWFMV-WXXKFALUSA-N
- SMILES
- C1(=CC=C(NS(=O)(=O)C)C=C1)C(O)CCCN(CC)CCCCCCC.C1(C(O)CCCN(CC)CCCCCCC)C=CC(NS(=O)(=O)C)=CC=1.C(/C(=O)O)=C\C(=O)O
- CAS DataBase Reference
- 122647 · 122647-32-9(CAS DataBase Reference)
- FDA UNII
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Ibutilide fumarate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 1
- hs_code
- 2935904000
- Toxicity
- rat,LD,oral,> 500mg/kg (500mg/kg),Teratology, The International Journal of Abnormal Development. Vol. 49, Pg. 406, 1994.
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H361d
- Hazard Classifications
- Acute Tox. 4 OralRepr. 2
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
IBUTILIDE FUMARATE
Antiarrhythmic [EPC]
MeSH Pharmacological Classification
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.
Applications
DescriptionCovert was launched in the US and UK for treatment of atrial fibrillation and flutter and can be synthesized in three steps from N-phenyl rnethanesulfonamide. While ibutilide has an asymmetric center, it has been determined that the racemate is equipotent with either enantiomer. The antiarrhythmic action is derived from the compounds ability to prolong the action potential duration and lengthen the refractory period of myocardial tissue. Class Ⅲ antiarrhythrnic agents accomplish this by blocking outward potassium channels, however, ibutilide elicits the same effect by activation of slow inward sodium channels. Recent evidence indicates that it also is a potent blocker of the rapidly acting delayed rectifier potassium current (lkr)and may block the ATP-inhibited potassium channel.
Description(±)-Ibutilide is a class III antiarrhythmic agent. It inhibits the rapidly activating delayed-rectifier potassium current (IKr) in AT-1 myocytes with an IC50 value of 20 nM. (±)-Ibutilide also enhances the late inward sodium current (INa) and increases the action potential duration in isolated guinea pig ventricular cells. It decreases ventricular fibrillation induced by the ATP-dependent potassium channel activator pinacidil in Langendorff isolated perfused rabbit hearts when used at concentrations ranging from 3 to 30 μM. (±)-Ibutilide (15 μg/kg, i.v.) increases the effective refractory period (ERP) of the left and right atrium in anesthetized pigs. It prevents rapid pacing-induced atrial flutter in dogs when administered orally at doses ranging from 0.25 to 5 mg/kg. Formulations containing ibutilide have been used in the treatment of atrial arrhythmias.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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