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

Details

Stereochemistry ACHIRAL
Molecular Formula C23H28ClN5O3.2ClH
Molecular Weight 530.875
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZIMILIDE DIHYDROCHLORIDE

SMILES

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

InChI

InChIKey=HHPSICLSNHCSNZ-BYEGLACWSA-N
InChI=1S/C23H28ClN5O3.2ClH/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;2*1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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
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 15:55:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:28 GMT 2023
Record UNII
6E6VJP68KR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZIMILIDE DIHYDROCHLORIDE
MI   USAN  
USAN  
Official Name English
AZIMILIDE DIHYDROCHLORIDE [MI]
Common Name English
AZIMILIDE HYDROCHLORIDE [MART.]
Common Name English
1-((5-(P-CHLOROPHENYL)FURFURYLIDENE)AMINO)-3-(4-(4-METHYL-1-PIPERAZINYL)BUTYL)HYDANTOIN DIHYDROCHLORIDE
Common Name English
NE-10064
Code English
AZIMILIDE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
Azimilide hydrochloride [WHO-DD]
Common Name English
AZIMILIDE DIHYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C93038
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
Code System Code Type Description
MERCK INDEX
m2174
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY Merck Index
FDA UNII
6E6VJP68KR
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
NCI_THESAURUS
C77977
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
PUBCHEM
9571003
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
USAN
GG-11
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
CAS
149888-94-8
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
EVMPD
SUB25697
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
EVMPD
SUB25698
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL123558
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
SMS_ID
100000090568
Created by admin on Fri Dec 15 15:55:28 GMT 2023 , Edited by admin on Fri Dec 15 15:55:28 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY