Indecainide
Identification
- Generic Name
- Indecainide
- DrugBank Accession Number
- DB00192
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 308.4174
Monoisotopic: 308.1888634 - Chemical Formula
- C20H24N2O
- Synonyms
- Indecainida
- Indecainide
- Indecainidum
Pharmacology
- Indication
For the treatment of life-threatening dysrhythmias and sustained ventricular tachycardia.
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- 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.
Target Actions Organism ASodium channel protein type 5 subunit alpha inhibitorHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Indecainide hydrochloride M76V0B96L5 73681-12-6 NXNSCUZKMVYAJQ-UHFFFAOYSA-N - International/Other Brands
- Decabid (Eli Lilly)
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Fluorenes
- Sub Class
- Not Available
- Direct Parent
- Fluorenes
- Alternative Parents
- Delta amino acids and derivatives / Aralkylamines / Fatty amides / Primary carboxylic acid amides / Dialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Amine / Amino acid or derivatives / Aralkylamine / Aromatic homopolycyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Delta amino acid or derivatives / Fatty acyl / Fatty amide
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 3AZF20DM1T
- CAS number
- 74517-78-5
- InChI Key
- 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
References
- General 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014338
- PubChem Compound
- 52195
- PubChem Substance
- 46506714
- ChemSpider
- 47194
- ChEBI
- 135314
- ChEMBL
- CHEMBL1201242
- ZINC
- ZINC000001855421
- Therapeutic Targets Database
- DAP000503
- PharmGKB
- PA164754881
- Wikipedia
- Indecainide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Eli lilly and co
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 94-95 °C PhysProp water solubility 1.88 mg/L Not Available logP 3.11 MANNHOLD,R ET AL. (1990) - Predicted Properties
Property Value Source Water Solubility 0.000896 mg/mL ALOGPS logP 3.24 ALOGPS logP 3.26 Chemaxon logS -5.5 ALOGPS pKa (Strongest Acidic) 16.51 Chemaxon pKa (Strongest Basic) 10.4 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 55.12 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 94.05 m3·mol-1 Chemaxon Polarizability 35.56 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9955 Blood Brain Barrier + 0.994 Caco-2 permeable + 0.5527 P-glycoprotein substrate Substrate 0.7322 P-glycoprotein inhibitor I Non-inhibitor 0.7405 P-glycoprotein inhibitor II Non-inhibitor 0.8525 Renal organic cation transporter Non-inhibitor 0.6101 CYP450 2C9 substrate Non-substrate 0.8006 CYP450 2D6 substrate Non-substrate 0.6619 CYP450 3A4 substrate Substrate 0.5911 CYP450 1A2 substrate Inhibitor 0.5715 CYP450 2C9 inhibitor Non-inhibitor 0.6947 CYP450 2D6 inhibitor Non-inhibitor 0.6213 CYP450 2C19 inhibitor Inhibitor 0.5978 CYP450 3A4 inhibitor Non-inhibitor 0.5383 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6169 Ames test Non AMES toxic 0.822 Carcinogenicity Non-carcinogens 0.8477 Biodegradation Not ready biodegradable 0.9814 Rat acute toxicity 2.3529 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9977 hERG inhibition (predictor II) Inhibitor 0.6032
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9050000000-db950638d7d29670ba20 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0069000000-b23434056a0066e1c069 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0049000000-54eb81e4569e1b465266 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0bt9-2194000000-e64482b18b60861a0c18 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-1393000000-b67ca4219f47f8d3dbed Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fk9-4590000000-64430e8e54bf0047bd62 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-3910000000-480852cfff57c29e33f6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.2640562 predictedDarkChem Lite v0.1.0 [M-H]- 187.1412562 predictedDarkChem Lite v0.1.0 [M-H]- 172.16873 predictedDeepCCS 1.0 (2019) [M+H]+ 187.5709562 predictedDarkChem Lite v0.1.0 [M+H]+ 188.2066562 predictedDarkChem Lite v0.1.0 [M+H]+ 174.52672 predictedDeepCCS 1.0 (2019) [M+Na]+ 187.6460562 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.3335562 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.61989 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- 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 pr...
- Gene Name
- SCN5A
- Uniprot ID
- Q14524
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Jaillon P, Drici M: Recent antiarrhythmic drugs. Am J Cardiol. 1989 Dec 5;64(20):65J-69J. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:35