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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24N2O.ClH
Molecular Weight 344.878
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDECAINIDE HYDROCHLORIDE

SMILES

Cl.CC(C)NCCCC1(C(N)=O)C2=C(C=CC=C2)C3=C1C=CC=C3

InChI

InChIKey=NXNSCUZKMVYAJQ-UHFFFAOYSA-N
InChI=1S/C20H24N2O.ClH/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);1H

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
Antiarrhythmic effects of indecainide in a drug-resistant population with ventricular tachycardia at programmed electrical stimulation.
1987 Jan
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 HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN  
USAN  
Official Name English
LY 135837
Code English
LY-135837
Code English
Indecainide hydrochloride [WHO-DD]
Common Name English
INDECAINIDE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
INDECAINIDE HYDROCHLORIDE [MART.]
Common Name English
LY-135857
Code English
DECABID
Brand Name English
INDECAINIDE HYDROCHLORIDE [MI]
Common Name English
9-[3-(Isopropylamino)propyl]fluorene-9-carboxamide monohydrochloride
Systematic Name English
INDECAINIDE HCL
Common Name English
9H-FLUORENE-9-CARBOXAMIDE, 9-(3-((1-METHYLETHYL)AMINO)PROPYL)-, MONOHYDROCHLORIDE
Common Name English
INDECAINIDE HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
Code System Code Type Description
PUBCHEM
52194
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
USAN
R-83
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
MERCK INDEX
m6247
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY Merck Index
DRUG BANK
DBSALT000880
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201242
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID60223950
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
NCI_THESAURUS
C65911
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
MESH
C042398
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
CAS
73681-12-6
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY
FDA UNII
M76V0B96L5
Created by admin on Fri Dec 15 15:19:13 UTC 2023 , Edited by admin on Fri Dec 15 15:19:13 UTC 2023
PRIMARY