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122647-32-9 molecular structure
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N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide

ChemBase ID: 193
Molecular Formular: C20H36N2O3S
Molecular Mass: 384.57644
Monoisotopic Mass: 384.24466402
SMILES and InChIs

SMILES:
c1(ccc(cc1)NS(=O)(=O)C)C(CCCN(CC)CCCCCCC)O
Canonical SMILES:
CCCCCCCN(CCCC(c1ccc(cc1)NS(=O)(=O)C)O)CC
InChI:
InChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3
InChIKey:
ALOBUEHUHMBRLE-UHFFFAOYSA-N

Cite this record

CBID:193 http://www.chembase.cn/molecule-193.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide
IUPAC Traditional name
@ibutilide
ibutilide
Brand Name
Corvert
Synonyms
Ibutilide Fumarate
Ibutilida [INN-Spanish]
Ibutilide
Ibutilidum [INN-Latin]
Ibutilide
(+/-)-N-[4-[4-(Ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide Fumarate
Corvert
U 70226E
Ibutilide Fumarate
CAS Number
122647-32-9
PubChem SID
160963656
46507904
PubChem CID
60753

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
TRC
I155400 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.720055  H Acceptors
H Donor LogD (pH = 5.5) -0.22546837 
LogD (pH = 7.4) 0.52760005  Log P 2.5426521 
Molar Refractivity 109.1816 cm3 Polarizability 43.551353 Å3
Polar Surface Area 69.64 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five true 
Log P 4.72  LOG S -4.91 
Solubility (Water) 4.73e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
100 mg/mL expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
112-117°C expand Show data source
Hydrophobicity(logP)
4.6 expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00308 external link
Item Information
Drug Groups approved
Description Ibutilide is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. [Wikipedia]
Indication Indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm.
Pharmacology Ibutilide prolongs the action potential duration and increases both atrial and ventricular refractoriness in vivo, i.e., class III electrophysiologic effects. Voltage clamp studies indicate that ibutilide, at nanomolar concentrations, delays repolarization by activation of a slow, inward current (predominantly sodium), rather than by blocking outward potassium currents, which is the mechanism by which most other class III antiarrhythmics act.
Toxicity Acute overdose in animals results in CNS toxicity; notably, CNS depression, rapid gasping breathing, and convulsions. The intravenous median lethal dose in the rat was more than 50 mg/kg which is, on a mg/m2 basis, at least 250 times the maximum recommended human dose.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic. Eight metabolites of ibutilide were detected in metabolic profiling of urine. These metabolites are thought to be formed primarily by o-oxidation followed by sequential b-oxidation of the heptyl side chain of ibutilide. Of the eight metabolites, only the o-hydroxy metabolite possesses class III electrophysiologic properties similar to that of ibutilide in an in vitro isolated rabbit myocardium model.
Absorption Rapid after intravenous injection
Half Life 6 hours (ranges from 2-12 hours)
Protein Binding 40%
Elimination In healthy male volunteers, about 82% of a 0.01 mg/kg dose of [14C] ibutilide fumarate was excreted in the urine (about 7% of the dose as unchanged ibutilide) and the remainder (about 19%) was recovered in the feces.
Distribution * 11 L/kg
Clearance * 29 mL/min/kg
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - I155400 external link
A methanesulfonanilide antiarrhythmic agent; prologns myocardial action potential duration, predominantly by activation of slow inward sodium current. Antiarrhythmic (class III).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Yang, T., et al.: Circulation, 91, 179 (1995)
  • • Stambler, B., et al.: Circulation, 94, 1613 (1995)
  • • Lee, K., et al.: J. Pharmacol. Exp. Ther., 286, 9 (1995)
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PATENTS

PATENTS

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INTERNET

INTERNET

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