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Identification
Name Indecainide
Accession Number DB00192 (APRD01032)
Type small molecule
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 9-(3-(Isopropylamino)propyl)-9-fluorenylcarboxamid
  • 9-(3-(Isopropylamino)propyl))fluorene-9-carboxamide
  • Indecainida [Spanish]
  • Indecainidum [Latin]
  • Ricainid
  • Ricainide
Synonyms
9-(3-(Isopropylamino)propyl)-9-fluorenylcarboxamid
9-(3-(Isopropylamino)propyl))fluorene-9-carboxamide
Indecainida [Spanish]
Indecainidum [Latin]
Ricainid
Ricainide
Salts Not Available
Brand names
Name Company
Decabid Eli Lilly
Brand mixtures Not Available
Categories
  • Antidysrhythmic Agents
  • Sodium channel blockers
CAS number 74517-78-5
Weight Average: 308.4174
Monoisotopic: 308.1888634
Chemical Formula C20H24N2O
InChI Key InChIKey=UCEWGESNIULAGX-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
9-{3-[(propan-2-yl)amino]propyl}-9H-fluorene-9-carboxamide
SMILES
CC(C)NCCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C12
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Biphenyl and Derivatives
  • Fluorenes
Substructures
  • Carbonyl Compounds
  • Aliphatic and Aryl Amines
  • Amino Ketones
  • Phenylpropenes
  • Benzene and Derivatives
  • Biphenyl and Derivatives
  • Fluorenes
  • Cyclopentadienes
  • Carbamates and Derivatives
  • Phenethylamines
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Carboxylic Acids and Derivatives
  • Indenes and Derivatives
Pharmacology
Indication For the treatment of life-threatening dysrhythmias and sustained ventricular tachycardia.
Pharmacodynamics 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.
Mechanism of action Indecainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.
Absorption Nearly complete following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 94-95 oC
Experimental Properties
Property Value Source
water solubility 1.88 mg/L PhysProp
logP 3.8 PhysProp
Predicted Properties
Property Value Source
water solubility 8.96e-04 g/l ALOGPS
logP 3.24 ALOGPS
logP 3.26 ChemAxon Molconvert
logS -5.5 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 55.12 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 94.05 ChemAxon Molconvert
polarizability 35.56 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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
External Links
Resource Link
PubChem Compound 52195 Link_out
PubChem Substance 46506714 Link_out
ChemSpider 47194 Link_out
Therapeutic Targets Database DAP000503 Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Sodium channel protein type 5 subunit alpha

Pharmacological action: yes
Actions: inhibitor

This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram

Organism class: human
UniProt ID: Q14524 Link_out
Gene: SCN5A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  4. Jaillon P, Drici M: Recent antiarrhythmic drugs. Am J Cardiol. 1989 Dec 5;64(20):65J-69J. Pubmed
  5. Holland DR, Lacefield WB, Gonzales CR, Johnston SR, Turk JA: Indecainide: effects on arrhythmias, electrophysiology, and cardiovascular dynamics. J Cardiovasc Pharmacol. 1989 Sep;14(3):454-61. Pubmed
  6. Steinberg MI, Wiest SA: Electrophysiological studies of indecainide hydrochloride, a new antiarrhythmic agent, in canine cardiac tissues. J Cardiovasc Pharmacol. 1984 Jul-Aug;6(4):614-21. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:40