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Details

Stereochemistry RACEMIC
Molecular Formula C18H28N2O3S
Molecular Weight 352.492
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALMOKALANT

SMILES

CCC[S@@+]([O-])CCCN(CC)C[C@@H](O)COC1=CC=C(C=C1)C#N

InChI

InChIKey=ZMHOBBKJBYLXFR-MZNJEOGPSA-N
InChI=1S/C18H28N2O3S/c1-3-11-24(22)12-5-10-20(4-2)14-17(21)15-23-18-8-6-16(13-19)7-9-18/h6-9,17,21H,3-5,10-12,14-15H2,1-2H3/t17-,24-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H28N2O3S
Molecular Weight 352.492
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Astra Hässle (now Hässle Läkemedel, a subsidiary of AstraZeneca) of Sweden was developing an IV formulation of almokalant for use in the treatment of atrial arrhythmias. Almokalant is a selective blocker of the delayed outward K+ current. Almokalant exhibited properties of a selective class III antiarrhythmic agent, devoid of β-blocking activity, in vitro and in vivo, in animals and humans. In humans, prolongation of the refractoriness of the atria and ventricles has been demonstrated, as well as a prolongation of the ventricular repolarization. A moderate antiarrhythmic efficacy has been disclosed in studies in patients with supraventricular reciprocating tachycardias, with atrial fibrillation and with premature ventricular contractions. Almokalant also has proarrhythmic potential and thedevelopment of almokalant was discontinued due to induction of Torsade de Pointes, which occurred in some susceptible patients during the clinical trials.

Originator

Curator's Comment: Almokalant was developed by Astra Hässle in the 1980s as an antiarrhythmic drug.

Approval Year

PubMed

PubMed

TitleDatePubMed
Refractory patterns and susceptibility to drug-induced polymorphic ventricular tachycardias in dogs with chronic atrioventricular block: relation to the type of anesthesia.
2002 Nov
Patents

Sample Use Guides

Ten post-myocardial infarction patients with complex ventricular arrhythmias were included and received, in randomized order on consecutive days, 4.5 mg (12.8 mumol) of almokalant or placebo intravenously over 10 minutes.
Route of Administration: Intravenous
In Vitro Use Guide
Transmembrane action potentials were recorded simultaneously from rabbit isolated ventricular muscle (VM) and Purkinje fibers (PF). At a basic cycle length (BCL) of 500 msec, the Class III agent almokalant (0.1 uM) increased the dispersion by prolonging the action potential duration (APD) significantly more in the PF (33% +/- 4.2%, n = 18) than in the VM (17% +/- 5.9%, n = 18, P < 0.05).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:05:52 UTC 2023
Edited
by admin
on Fri Dec 15 16:05:52 UTC 2023
Record UNII
I9NG89L275
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALMOKALANT
INN  
INN  
Official Name English
almokalant [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
NCI_THESAURUS C93038
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
Code System Code Type Description
SMS_ID
100000087442
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
EVMPD
SUB05349MIG
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
MESH
C074334
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
FDA UNII
I9NG89L275
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
PUBCHEM
54554626
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID40869693
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
NCI_THESAURUS
C77828
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
WIKIPEDIA
ALMOKALANT
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL362103
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
CAS
123955-10-2
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
INN
6651
Created by admin on Fri Dec 15 16:05:52 UTC 2023 , Edited by admin on Fri Dec 15 16:05:52 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY