BISARAMIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H23ClN2O2
Molecular Weight	322.83
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C[C@@H]2CN(C)C[C@H](C1)[C@@H]2OC(=O)C3=CC=C(Cl)C=C3

InChI

InChIKey=PMCPYLGCPSNSLS-FOLVSLTJSA-N

InChI=1S/C17H23ClN2O2/c1-3-20-10-13-8-19(2)9-14(11-20)16(13)22-17(21)12-4-6-15(18)7-5-12/h4-7,13-14,16H,3,8-11H2,1-2H3/t13-,14+,16+

HIDE SMILES / InChI

Molecular Formula	C17H23ClN2O2
Molecular Weight	322.83
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1684242 | https://adisinsight.springer.com/drugs/800001220 | https://www.ncbi.nlm.nih.gov/pubmed/9544797

Bisaramil, an antiarrhythmic drug was developed as an inhibitor of calcium transport and as a membrane stabilizer. In addition, the drug showed tonic and frequency-dependent block that is most potent against the heart Na+ channel. However, the phase-II for Arrhythmias in Japan was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Antiarrhythmic effects of bisaramil on triggered arrhythmias produced by intracoronary injection of digitalis and adrenaline in the dog.	1995-05	7494388
The effects of bisaramil on experimental arrhythmias.	1990-07-01	2402479
High-performance liquid chromatographic method for quantitative determination of Yutac, a new antiarrhythmic agent, in dog plasma.	1985-03-22	3998028

Sample Use Guides

In Vivo Use Guide

Six healthy volunteers received an oral dose of 100 mg and an intravenous dose of 35 mg of bisaramil in a cross over study

Route of Administration: Other

In Vitro Use Guide

In isolated cardiac myocytes bisaramil directly blocks sodium currents with IC50 values of 13μM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:54 GMT 2025`
Record UNII	FVT2ESG270
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BISARAMIL

Official Name

English

SYN-3-ETHYL-7-METHYL-3,7-DIAZABICYCLO(3.3.1)NON-9-YL P-CHLOROBENZOATE

Preferred Name

English

bisaramil [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47793