U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H28ClN5O3
Molecular Weight 457.953
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZIMILIDE

SMILES

CN1CCN(CCCCN2C(=O)CN(\N=C\C3=CC=C(O3)C4=CC=C(Cl)C=C4)C2=O)CC1

InChI

InChIKey=MREBEPTUUMTTIA-PCLIKHOPSA-N
InChI=1S/C23H28ClN5O3/c1-26-12-14-27(15-13-26)10-2-3-11-28-22(30)17-29(23(28)31)25-16-20-8-9-21(32-20)18-4-6-19(24)7-5-18/h4-9,16H,2-3,10-15,17H2,1H3/b25-16+

HIDE SMILES / InChI

Molecular Formula C23H28ClN5O3
Molecular Weight 457.953
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Azimilide is a class III antiarrhythmic agent that prolongs cardiac repolarisation by blocking both the rapidly and slowly activating components of the delayed rectifier potassium channel. The most important consequence of this is apparent rate-independent activity, so that, unlike other class III antiarrhythmics, azimilide does not lose efficacy at high heart rates. Azimilide has very predictable pharmacokinetics, is predominantly hepatically metabolized, and has no significant drug interactions with digoxin or warfarin. The most common adverse effects reported by patients on azimilide were approximately equal in frequency with those on placebo: headache, asthenia, infection, diarrhea and dizziness. Azimilide is in phase III clinical trials for the treatment both supraventricular and ventricular tachyarrhythmias.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
610.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Azimilide dihydrochloride: a unique class III antiarrhythmic agent.
1999 May-Jun
Effects of azimilide, a new class III antiarrhythmic drug, on reentrant circuits causing ventricular tachycardia and fibrillation in a canine model of myocardial infarction.
2001 Sep
Influence of coadministration on the pharmacokinetics of azimilide dihydrochloride and digoxin.
2005 Jul
The metabolic profile of azimilide in man: in vivo and in vitro evaluations.
2005 Sep
Patents

Sample Use Guides

100 and 125 mg once daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:15:31 UTC 2023
Edited
by admin
on Fri Dec 15 16:15:31 UTC 2023
Record UNII
74QU6P2934
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZIMILIDE
INN   MI   WHO-DD  
INN  
Official Name English
1-((5-(P-CHLOROPHENYL)FURFURYLIDENE)AMINO)-3-(4-(4-METHYL-1-PIPERAZINYL)BUTYL)HYDANTOIN
Common Name English
Azimilide [WHO-DD]
Common Name English
2,4-IMIDAZOLIDINEDIONE, 1-(((5-(4-CHLOROPHENYL)-2-FURANYL)METHYLENE)AMINO)-3-(4-(4-METHYL-1-PIPERAZINYL)BUTYL)-
Systematic Name English
AZIMILIDE [MI]
Common Name English
azimilide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C93038
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C79923
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
MESH
C086123
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
PUBCHEM
9571004
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
FDA UNII
74QU6P2934
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL123558
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
DRUG CENTRAL
274
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
INN
7299
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
MERCK INDEX
m2174
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY Merck Index
EVMPD
SUB05657MIG
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
SMS_ID
100000086104
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
WIKIPEDIA
AZIMILIDE
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
DRUG BANK
DB04957
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID10869988
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
CAS
149908-53-2
Created by admin on Fri Dec 15 16:15:31 UTC 2023 , Edited by admin on Fri Dec 15 16:15:31 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Useful to treat cardiac arrhythmia