AMBASILIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H25N3O
Molecular Weight	335.4427
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=C(C=C1)C(=O)N2C[C@H]3C[C@H](CN(CC4=CC=CC=C4)C3)C2

InChI

InChIKey=DLNAKYFPFYUBDR-HDICACEKSA-N

InChI=1S/C21H25N3O/c22-20-8-6-19(7-9-20)21(25)24-14-17-10-18(15-24)13-23(12-17)11-16-4-2-1-3-5-16/h1-9,17-18H,10-15,22H2/t17-,18+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15738585 | https://www.ncbi.nlm.nih.gov/pubmed/11033107 | https://www.ncbi.nlm.nih.gov/pubmed/10566046

Ambasilide, a class III antiarrhythmic, has been shown to block multiple cardiac channels in a variety of animals including humans. Ambasilide is a potassium channel antagonist. Ambasilide has multichannel blocking properties including beta-adrenergic antagonism.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
HERG 99 Target ID: CHEMBL240 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D09758 \| https://www.ncbi.nlm.nih.gov/pubmed/8717164 \| https://www.ncbi.nlm.nih.gov/pubmed/11033107	Inhibitor 8504	3.6 µM [IC50]
Voltage-gated potassium channel subunit Kv7.1 3 Target ID: CHEMBL1866 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D09758	Inhibitor 8504
sodium ion transport 14 Target ID: GO:0006814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8717164	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Arrhythmia 45 Sources: http://adisinsight.springer.com/drugs/800001764 https://www.ncbi.nlm.nih.gov/pubmed/7923691 https://www.ncbi.nlm.nih.gov/pubmed/8717164	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of ambasilide in isolated perfused guinea pig heart: use dependence.	2005	15738585
Analysis of the electrophysiological effects of ambasilide, a new antiarrhythmic agent, in canine isolated ventricular muscle and purkinje fibers.	2000-02	10974415
Clinical potential of emerging antiarrhythmic agents.	1999-04	10566046
Effects of the class III antiarrhythmic drug ambasilide on outward currents in human atrial myocytes.	1996-01	8717164

Patents

Sample Use Guides

In Vivo Use Guide

Cats: ambasilide, 5 mg/kg intravenous (i.v.) bolus plus 5 mg.kg-1.hr-1 i.v. infusion

Route of Administration: Intravenous

In Vitro Use Guide

Ambasilide (10 uM/L) produced a more marked prolongation of APD(90) at lower stimulation frequencies in Purkinje fibers (at CL of 2000 ms = 56.0 +/- 16.1%, n = 6, versus CL of 400 ms = 15.1 +/- 3.7%, n = 6; p < 0.05), but, in 20 microM/l, this effect was considerably diminished (15.2 +/- 3.6%, n = 6, versus 7.3 +/- 5.1%, n = 6, p < 0.05).

Name

Type

Language

3-(P-AMINOBENZOYL)-7-BENZYL-3,7-DIAZABICYCLO(3.3.1)NONANE

Preferred Name

English

AMBASILIDE

Official Name

English

ambasilide [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47793