Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H28N2O2 |
Molecular Weight | 352.4699 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1)C(=O)NC2=C(CCC3CCCCN3C)C=CC=C2
InChI
InChIKey=PJWPNDMDCLXCOM-UHFFFAOYSA-N
InChI=1S/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)
DescriptionSources: https://www.drugs.com/pro/enkaid.htmlCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01228 | https://www.ncbi.nlm.nih.gov/pubmed/8230126
Sources: https://www.drugs.com/pro/enkaid.html
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01228 | https://www.ncbi.nlm.nih.gov/pubmed/8230126
Encainide is an antiarrhythmic drug, developed by Bristol Myers Co supplied 25 and 35 mg capsules for oral administration. Encainide is no longer used because of its frequent proarrhythmic side effects. The mechanisms of the antiarrhythmic effects of Enkaid are unknown but probably are the result of its ability to slow conduction, reduce membrane responsiveness, inhibit automaticity, and increase the ratio of the effective refractory period to action potential duration. Enkaid produces a differentially greater effect on the ischemic zone as compared with normal cells in the myocardium. This could result in the elimination of the disparity in the electrophysiologic properties between these two zones and eliminate pathways of abnormal impulse conduction, development of boundary currents and/or sites of abnormal impulse generation. The absorption of Enkaid after oral administration is nearly complete with peak plasma levels present 30 to 90 minutes after dosing. There are two major genetically determined patterns of encainide metabolism. In over 90% of patients, the drug is rapidly and extensively metabolized with an elimination half-life of 1 to 2 hours. These patients convert encainide to two active metabolites, O-demethylencainide (ODE) and 3-methoxy-O-demethylencainide (MODE), that are more active (on a per mg basis) than encainide itself. In less than 10% of patients, metabolism of encainide is slower and the estimated encainide elimination half-life is 6 to 11 hours. Slow metabolism of encainide is associated with a diminished ability to metabolize debrisoquin. Enkaid should be administered only after appropriate clinical assessment and the dosage of Enkaid must be individualized for each patient on the basis of therapeutic response and tolerance. The recommended initial dosing schedule for adults is one 25 mg Enkaid capsule t.i.d. at approximately 8-hour intervals.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8230126 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Enkaid Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
75.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg 3 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
151 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg 3 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
60.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
100.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
147 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg 3 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
416 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg 3 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
124 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
747 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
335 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
641 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg 3 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg 3 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1909559 |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENCAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg 3 times / day multiple, oral Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 24-83 years n = 17 Health Status: unhealthy Condition: benign or potentially lethal ventricular arrhythmias Age Group: 24-83 years Sex: M+F Population Size: 17 Sources: |
Disc. AE: Fatigue... AEs leading to discontinuation/dose reduction: Fatigue (severe, 1 patient) Sources: |
75 mg 4 times / day multiple, oral Studied dose Dose: 75 mg, 4 times / day Route: oral Route: multiple Dose: 75 mg, 4 times / day Sources: |
unhealthy, 57 years n = 111 Health Status: unhealthy Condition: Ventricular Arrhythmias Age Group: 57 years Sex: M+F Population Size: 111 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fatigue | severe, 1 patient Disc. AE |
50 mg 3 times / day multiple, oral Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, 24-83 years n = 17 Health Status: unhealthy Condition: benign or potentially lethal ventricular arrhythmias Age Group: 24-83 years Sex: M+F Population Size: 17 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Reevaluation of digoxin-encainide interactions using an animal model. | 1988 Jul |
|
Fetal tachyarrhythmia - part II: treatment. | 2004 Oct 1 |
|
Role of cytochrome P450 in drug interactions. | 2008 Oct 18 |
|
Update on terbinafine with a focus on dermatophytoses. | 2009 Apr 21 |
|
Complex correlation measure: a novel descriptor for Poincaré plot. | 2009 Aug 13 |
|
Challenging cardiac electrophysiology. | 2010 |
|
EVITA: a tool for the early evaluation of pharmaceutical innovations with regard to therapeutic advantage. | 2010 Mar 16 |
|
Effectiveness of prophylactic implantation of cardioverter-defibrillators without cardiac resynchronization therapy in patients with ischaemic or non-ischaemic heart disease: a systematic review and meta-analysis. | 2010 Nov |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/enkaid.html#DosAdmin
The recommended initial dosing schedule for adults is one 25 mg Enkaid capsule t.i.d. at approximately 8-hour intervals. After a period of 3 to 5 days, the dosage may be increased to 35 mg t.i.d. if necessary. If the desired therapeutic response is not achieved after an additional 3 to 5 days, the dose may again be adjusted to 50 mg t.i.d. Rapid dose escalation should be avoided.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8230126
Homogenates of neuronal membrane vesicles were freshly prepraed from the cortex of male Sprague-Dawley. Vesicular homogenate were added to an incubation buffer containing [3H]batrachotoxinin benzoate (3H-BTX-B) (56.8 Ci/mmol; 10 nM final concentration); Leiurus quinquestriatus (Lqq) North African scorpion venom (17 mkM); tetrodotoxin (1.0 mkM), and unlabeled Encainide. Preparations were incubated at 37 OC for 2 h, followed by rapid filtration through Whatman GF/C filters using 10 mL per tube of ice cold wash buffer. Total radioactivity bound to neural membranes was determined by liquid scintillation spectrometry.
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WHO-VATC |
QC01BC08
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WHO-ATC |
C01BC08
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NCI_THESAURUS |
C93038
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NCI_THESAURUS |
C47793
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DTXSID0022983
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100000080224
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ENCAINIDE
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SY3J0147NB
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48041
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D016700
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1007
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4472
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SUB06519MIG
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DB01228
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C65511
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66778-36-7
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CHEMBL315838
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42368
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m4895
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4788
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)