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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24N2O
Molecular Weight 308.4181
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDECAINIDE

SMILES

CC(C)NCCCC1(c2ccccc2-c3ccccc31)C(=N)O

InChI

InChIKey=UCEWGESNIULAGX-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Indecainide, an antiarrhythmic agent classified as type IC. Class IC drugs greatly depress intracardiac conduction and are the most potent antiarrhythmic compounds able to suppress ventricular premature beats. Indecainide was used under brand name decabid for the treatment of life-threatening dysrhythmias and sustained ventricular tachycardia. However, that usage was discontinued. Indecainide have mediated the pharmacological actions through a blocking of Na+-channel.

Originator

Curator's Comment:: # Eli Lilly

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DECABID

Approved Use

Unknown

Launch Date

6.3089279E11
Primary
DECABID

Approved Use

Unknown

Launch Date

6.3089279E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
37 ng/mL
248 mg 1 times / day multiple, oral
dose: 248 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DESISOPROPYL INDECAINIDE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
409 ng/mL
248 mg 1 times / day multiple, oral
dose: 248 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
INDECAINIDE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.7 h
248 mg 1 times / day multiple, oral
dose: 248 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DESISOPROPYL INDECAINIDE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
10.3 h
248 mg 1 times / day multiple, oral
dose: 248 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
INDECAINIDE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
400 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 400 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 67 years
n = 10
Health Status: unhealthy
Age Group: 67 years
Sex: M+F
Population Size: 10
Sources:
Other AEs: Nausea, Numbness of lip...
Other AEs:
Nausea (1 patient)
Numbness of lip (1 patient)
Numbness of tongue (1 patient)
Sources:
100 mg 4 times / day multiple, oral
Studied dose
Dose: 100 mg, 4 times / day
Route: oral
Route: multiple
Dose: 100 mg, 4 times / day
Sources:
unhealthy
n = 11
Health Status: unhealthy
Sex: M+F
Population Size: 11
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea 1 patient
400 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 400 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 67 years
n = 10
Health Status: unhealthy
Age Group: 67 years
Sex: M+F
Population Size: 10
Sources:
Numbness of lip 1 patient
400 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 400 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 67 years
n = 10
Health Status: unhealthy
Age Group: 67 years
Sex: M+F
Population Size: 10
Sources:
Numbness of tongue 1 patient
400 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 400 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 67 years
n = 10
Health Status: unhealthy
Age Group: 67 years
Sex: M+F
Population Size: 10
Sources:
PubMed

PubMed

TitleDatePubMed
Indecainide for treatment of ventricular ectopic depolarizations: efficacy, pharmacokinetics, hemodynamic effects and safety.
1988 Apr
Indecainide: effects on arrhythmias, electrophysiology, and cardiovascular dynamics.
1989 Sep
Effect of indecainide in patients with left ventricular dysfunction.
1990 Nov

Sample Use Guides

ventricular arrhythmias: an open-label intravenous trail in 10 patients was conducted using a dose of 1.7 mg/kg/min under constant monitoring. An oral short-term in-hospital trial in 20 patients (8 patients entered directly from the intravenous short-term trial) was conducted using a single-blind placebo dose titration protocol in which 50 mg of indecainide every 8 hours was increased at 3-day intervals to 75 mg, and then 100 mg every 8 hours depending on the observed change in ventricular arrhythmia frequency by Holter monitoring. Finally, an outpatient long-term oral trial was conducted in 17 of the 20 patients who completed the inpatient oral short-term trail.
Route of Administration: Other
In Vitro Use Guide
The effects of indecainide have been studied on rabbit sinoatrial (SA) node and atrioventricular (AV) node. Indecainide at concentrations up to 2.9 mumol/L in 5 preparations did not produce a sinus bradycardia, nor reduce the maximum rate of rise of the intracellular action potential of sinus node cells, but it did antagonize the tachycardia induced by increasing the extracellular calcium concentration. Indecainide slightly prolonged AV conduction time [from 49.07 +/- 4.43 ms to 57.37 +/- 0.90 ms at 2.9 mumol/L (means +/- SEM in four preparations)], but this small delay could be attributed to slowing of conduction in atrial fibres leading to the node, rather than to an effect on the AV nodal cells themselves. It is concluded that indecainide does not block channels carrying inward calcium current in nodal tissues.
Name Type Language
INDECAINIDE
INN   MI   WHO-DD  
INN  
Official Name English
INDECAINIDE [MI]
Common Name English
9H-FLUORENE-9-CARBOXAMIDE, 9-(3-((1-METHYLETHYL)AMINO)PROPYL)-
Systematic Name English
INDECAINIDE [WHO-DD]
Common Name English
9-(3-(ISOPROPYLAMINO)PROPYL)FLUORENE-9-CARBOXAMIDE
Systematic Name English
INDECAINIDE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
Code System Code Type Description
EVMPD
SUB08171MIG
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
EPA CompTox
74517-78-5
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
NCI_THESAURUS
C65910
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
FDA UNII
3AZF20DM1T
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
DRUG CENTRAL
1434
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
MESH
C042398
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
MERCK INDEX
M6247
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY Merck Index
INN
5116
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
DRUG BANK
DB00192
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201242
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
CAS
74517-78-5
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
WIKIPEDIA
INDECAINIDE
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY
PUBCHEM
52195
Created by admin on Sat Jun 26 02:38:33 UTC 2021 , Edited by admin on Sat Jun 26 02:38:33 UTC 2021
PRIMARY