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Identification
NameIndecainide
Accession NumberDB00192  (APRD01032)
TypeSmall Molecule
GroupsApproved
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
Synonyms
Indecainida
Indecainide
Indecainidum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DecabidEli Lilly
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Indecainide hydrochloride
ThumbNot applicableDBSALT000880
Categories
UNII3AZF20DM1T
CAS number74517-78-5
WeightAverage: 308.4174
Monoisotopic: 308.1888634
Chemical FormulaC20H24N2O
InChI KeyInChIKey=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)
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fluorenes. These are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassFluorenes
Sub ClassNot Available
Direct ParentFluorenes
Alternative Parents
Substituents
  • Fluorene
  • Delta amino acid or derivatives
  • Aralkylamine
  • Fatty acyl
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of life-threatening dysrhythmias and sustained ventricular tachycardia.
PharmacodynamicsIndecainide 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 actionIndecainide 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.
Related Articles
AbsorptionNearly complete following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityWhen 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9955
Blood Brain Barrier+0.994
Caco-2 permeable+0.5527
P-glycoprotein substrateSubstrate0.7322
P-glycoprotein inhibitor INon-inhibitor0.7405
P-glycoprotein inhibitor IINon-inhibitor0.8525
Renal organic cation transporterNon-inhibitor0.6101
CYP450 2C9 substrateNon-substrate0.8006
CYP450 2D6 substrateNon-substrate0.6619
CYP450 3A4 substrateSubstrate0.5911
CYP450 1A2 substrateInhibitor0.5715
CYP450 2C9 inhibitorNon-inhibitor0.6947
CYP450 2D6 inhibitorNon-inhibitor0.6213
CYP450 2C19 inhibitorInhibitor0.5978
CYP450 3A4 inhibitorNon-inhibitor0.5383
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6169
Ames testNon AMES toxic0.822
CarcinogenicityNon-carcinogens0.8477
BiodegradationNot ready biodegradable0.9814
Rat acute toxicity2.3529 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9977
hERG inhibition (predictor II)Inhibitor0.6032
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point94-95 °CPhysProp
water solubility1.88 mg/LNot Available
logP3.11MANNHOLD,R ET AL. (1990)
Predicted Properties
PropertyValueSource
Water Solubility0.000896 mg/mLALOGPS
logP3.24ALOGPS
logP3.26ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)16.51ChemAxon
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.05 m3·mol-1ChemAxon
Polarizability35.56 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  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:2225716 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function:
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 respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
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:17139284 ]
  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:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Jaillon P, Drici M: Recent antiarrhythmic drugs. Am J Cardiol. 1989 Dec 5;64(20):65J-69J. [PubMed:2688391 ]
  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:2476626 ]
  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:6206315 ]
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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 16:44