TRANSCAINIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H35N3O2
Molecular Weight	373.5322
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)C1(CCN(CC1)[C@@H]2CCCC[C@H]2O)C(=O)NC3=C(C)C=CC=C3C

InChI

InChIKey=MFKCGXDCHAFQQZ-RTBURBONSA-N

InChI=1S/C22H35N3O2/c1-16-8-7-9-17(2)20(16)23-21(27)22(24(3)4)12-14-25(15-13-22)18-10-5-6-11-19(18)26/h7-9,18-19,26H,5-6,10-15H2,1-4H3,(H,23,27)/t18-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H35N3O2
Molecular Weight	373.5322
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2459527 | https://www.ncbi.nlm.nih.gov/pubmed/1665791 | https://adisinsight.springer.com/drugs/800000444

Transcainide is a new and very potent analog of lidocaine that has been found effective in the treatment of ventricular arrhythmias. In common with other class I antiarrhythmic drugs its main electrophysiologic effect is a reduction of the upstroke velocity of the action potential (Vmax) suggesting a blockade of the sodium channel. The interaction of transcainide with this receptor is reversible and state-dependent. Transcainide characterized by very slow kinetics of binding and unbinding to the activated "open" Na+ channel. Transcainide had been in phase II clinical trial for the treatment of Arrhythmias. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Late massive hemoptysis after transbronchial biopsy of hamartoma: an involvement of pulmonary artery and vein.	2007-12	18292723
Transcainide causes two modes of open-channel block with different voltage sensitivities in batrachotoxin-activated sodium channels.	1994-09	7811913
Class I antiarrhythmic drugs: allosteric inhibitors of [3H] batrachotoxinin binding to rat cardiac sodium channels.	1994-01	8301556
Clinical and electrophysiologic studies of R61748 (transcainide): a new class Ic antiarrhythmic drug.	1992	1378674
Transcainide: biochemical evidence for state-dependent interaction with the class I antiarrhythmic drug receptor.	1991-10-02	1665791
Slowly developing activation block of cardiac sodium channels by a lidocaine analog, transcainide.	1988-07	2459527
Electrophysiologic, antiarrhythmic and hemodynamic effects of transcainide.	1987-06	3632145
Sodium channel block by a potent, new antiarrhythmic agent, transcainide, in guinea pig ventricular myocytes.	1987-06	2442531
Cardiac electrophysiologic effects of R 54718.	1987-03-03	3569425
Evaluation of the efficacy and tolerance of the antiarrhythmic agent transcainide (R 54718).	1987	2441995

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:09:36 GMT 2025` Edited by `admin` on `Mon Mar 31 18:09:36 GMT 2025`
Record UNII	5VSP2X37QG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRANSCAINIDE

Official Name

English

R 54,718

Preferred Name

English

TRANSCAINIDE [USAN]

Common Name

English

TRANSCAINIDE [MART.]

Common Name

English

transcainide [INN]

Common Name

English

(±)-TRANS-4-(DIMETHYLAMINO)-1-(2-HYDROXYCYCLOHEXYL)-2',6'-ISONIPECTOXYLIDIDE

Common Name

English

4-PIPERIDINECARBOXAMIDE, 4-(DIMETHYLAMINO)-N-(2,6-DIMETHYLPHENYL)-1-(2-HYDROXYCYCLOHEXYL)-, TRANS-(±)-

Common Name

English

R-54718

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47793