9-{3-[(propan-2-yl)amino]propyl}-9H-fluorene-9-carboxamide

• ChemBase ID: 77
• Molecular Formular: C20H24N2O
• Molecular Mass: 308.41736
• Monoisotopic Mass: 308.1888634
• SMILES: O=C(N)C1(CCCNC(C)C)c2c(c3c1cccc3)cccc2
• Canonical SMILES: CC(NCCCC1(C(=O)N)c2ccccc2c2c1cccc2)C
• InChI: InChI=1S/C20H24N2O/c1-14(2)22-13-7-12-20(19(21)23)17-10-5-3-8-15(17)16-9-4-6-11-18(16)20/h3-6,8-11,14,22H,7,12-13H2,1-2H3,(H2,21,23)
• InChIKey: UCEWGESNIULAGX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-{3-[(propan-2-yl)amino]propyl}-9H-fluorene-9-carboxamide
• IUPAC Traditional name: indecainide
• Brand Name: Decabid
• Synonyms: Ricainid; Ricainide; Indecainidum [Latin]; Indecainida [Spanish]; 9-(3-(Isopropylamino)propyl)-9-fluorenylcarboxamid; 9-(3-(Isopropylamino)propyl))fluorene-9-carboxamide; Indecainide

Database IDs

• CAS Number: 74517-78-5
• PubChem SID: 46506714; 160963540
• PubChem CID: 52195

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.50598
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.029690318
• LogD (pH = 7.4): 0.4556179
• Log P: 3.2623758
• Molar Refractivity: 94.0462 cm^3
• Polarizability: 38.09791 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.24
• LOG S: -5.54
• Solubility (Water): 8.96e-04 g/l

PROPERTIES

Physical Property

• Solubility: 1.88 mg/L
• Hydrophobicity(logP): 3.8

DETAILS

DrugBank - DB00192

• Drug Groups: approved
• Description: Indecainide is a rarely used antidysrhythmic. Indecainide has local anesthetic activity and belongs to the membrane stabilizing (Class 1) group of antiarrhythmic agents; it has electrophysiologic effects characteristic of the IC class of antiarrhythmics.
• Indication: For the treatment of life-threatening dysrhythmias and sustained ventricular tachycardia.
• Pharmacology: Indecainide is a rarely used antidysrhythmic. Indecainide has local anesthetic activity and belongs to the membrane stabilizing (Class 1) group of antiarrhythmic agents; it has electrophysiologic effects characteristic of the IC class of antiarrhythmics.
• Toxicity: When given orally to either young adult rats or mice, the LD50 was 100 mg/kg. Symptoms of overdose include nausea and vomiting, convulsions, hypotension, bradycardia, syncope, extreme widening of the QRS complex, widening of the QT interval, widening of the PR interval, ventricular tachycardia, AV nodal block, asystole, bundle branch block, cardiac failure, and cardiac arrest.
• Affected Organisms: Humans and other mammals
• Absorption: Nearly complete following oral administration.
• References: Giardina EV, Saroff AL, Schneider M: Effect of indecainide in patients with left ventricular dysfunction. Clin Pharmacol Ther. 1990 Nov;48(5):582-9. [Pubmed]

REFERENCES

• Giardina EV, Saroff AL, Schneider M: Effect of indecainide in patients with left ventricular dysfunction. Clin Pharmacol Ther. 1990 Nov;48(5):582-9. Pubmed