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 IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Indecainide hydrochlorideM76V0B96L5 73681-12-6NXNSCUZKMVYAJQ-UHFFFAOYSA-NDetails
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
CategoriesNot Available
UNII3AZF20DM1T
CAS number74517-78-5
WeightAverage: 308.4174
Monoisotopic: 308.1888634
Chemical FormulaC20H24N2O
InChI KeyUCEWGESNIULAGX-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
Pharmacology
Indication

For the treatment of life-threatening dysrhythmias and sustained ventricular tachycardia.

Structured Indications Not Available
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium channel protein type 5 subunit alphaProteinyes
inhibitor
HumanQ14524 details
Related Articles
Absorption

Nearly complete following oral administration.

Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot 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
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)94-95 °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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassFluorenes
Direct ParentFluorenes
Alternative ParentsDelta amino acids and derivatives / Aralkylamines / Fatty amides / Primary carboxylic acid amides / Dialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsDelta amino acid or derivatives / Fluorene / Aralkylamine / Fatty amide / Fatty acyl / Amino acid or derivatives / Carboxamide group / Primary carboxylic acid amide / Carboxylic acid derivative / Secondary aliphatic amine
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot 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 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:46