Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:14:08 UTC |
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Update Date | 2014-12-24 20:26:56 UTC |
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Accession Number | T3D4738 |
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Identification |
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Common Name | Encainide |
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Class | Small Molecule |
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Description | All drug products containing encainide hydrochloride. Encainide hydrochloride, formerly marketed as Enkaid capsules, was associated with increased death rates in patients who had asymptomatic heart rhythm abnormalities after a recent heart attack. The manufacturer of Enkaid capsules voluntarily withdrew the product from the US market on December 16, 1991. |
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Compound Type | - Amide
- Amine
- Anti-Arrhythmia Agent
- Drug
- Ester
- Ether
- Organic Compound
- Sodium Channel Blocker
- Synthetic Compound
- Voltage-Gated Sodium Channel Blocker
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Chemical Structure | |
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Synonyms | Synonym | (+-)-2'-[2-(1-Methyl-2-piperidyl)ethyl]-P-anisanilide | (+-)-4-Methoxy-N-(2-(2-(1-methyl-2-piperidinyl)ethyl)phenyl)benzamide | 4-Methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide | 4-Methoxy-N-{2-[2-(1-methyl-piperidin-2-yl)-ethyl]-phenyl}-benzamide | Encainida | Encainidum | Enkaid |
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Chemical Formula | C22H28N2O2 |
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Average Molecular Mass | 352.470 g/mol |
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Monoisotopic Mass | 352.215 g/mol |
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CAS Registry Number | 66778-36-7 |
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IUPAC Name | 4-methoxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamide |
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Traditional Name | encainide |
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SMILES | COC1=CC=C(C=C1)C(=O)NC1=CC=CC=C1CCC1CCCCN1C |
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InChI Identifier | InChI=1/C22H28N2O2/c1-24-16-6-5-8-19(24)13-10-17-7-3-4-9-21(17)23-22(25)18-11-14-20(26-2)15-12-18/h3-4,7,9,11-12,14-15,19H,5-6,8,10,13,16H2,1-2H3,(H,23,25) |
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InChI Key | InChIKey=PJWPNDMDCLXCOM-UHFFFAOYNA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Anilides |
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Direct Parent | Benzanilides |
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Alternative Parents | |
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Substituents | - Benzanilide
- Benzamide
- Benzoic acid or derivatives
- Alkaloid or derivatives
- Anisole
- Phenoxy compound
- Benzoyl
- Phenol ether
- Methoxybenzene
- Aralkylamine
- Alkyl aryl ether
- Piperidine
- Amino acid or derivatives
- Carboxamide group
- Tertiary aliphatic amine
- Tertiary amine
- Secondary carboxylic acid amide
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Ether
- Hydrocarbon derivative
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available | LogP | 4 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-052n-9311000000-985044a85c7ca1fc4601 | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0019000000-c3aba8c66a81550a1bc5 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-4489000000-fb4fa7dd76074a147422 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbc-9741000000-30c243030c2a40b68b44 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-ace9a97974ab75eb724b | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1219000000-8488789ae9ebc4c00e17 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9511000000-c16ae5ec1e6ea9df3fb7 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udr-0509000000-1dacce0088b2fb6df452 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-2922000000-d0a2447f1a18ba018bdd | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aov-9500000000-bcebe1c95f279236a417 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-af987e6024645b1a42dc | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zfr-4449000000-97433c4f98db5b174197 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9231000000-7c8bacd1fef271451d2b | 2021-10-11 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Encainide is a sodium channel blocker, binding to voltage gated sodium channels. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole. |
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Metabolism | Route of Elimination: A radiolabeled dose of encainide is excreted in approximately equal amounts in the urine and feces.
Half Life: 1-2 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Encainide is a class Ic antiarrhythmic agent which was used for management of irregular heartbeats, such as atrial fibrillation, atrial flutter, ventricular tachycardia, and ventricular fibrillation. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01228 |
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HMDB ID | Not Available |
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PubChem Compound ID | Not Available |
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ChEMBL ID | CHEMBL570071 |
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ChemSpider ID | Not Available |
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KEGG ID | C06978 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 4788 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Encainide |
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References |
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Synthesis Reference | DrugSyn.org |
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MSDS | Not Available |
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General References | Not Available |
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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