TEDISAMIL SESQUIFUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C19H32N2.3C4H4O4
Molecular Weight	925.158
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.C(C1CC1)N2CC3CN(CC4CC4)CC(C2)C35CCCC5.C(C6CC6)N7CC8CN(CC9CC9)CC(C7)C8%10CCCC%10

InChI

InChIKey=AZPYPAVFNGFTGB-VQYXCCSOSA-N

InChI=1S/2C19H32N2.3C4H4O4/c2*1-2-8-19(7-1)17-11-20(9-15-3-4-15)12-18(19)14-21(13-17)10-16-5-6-16;3*5-3(6)1-2-4(7)8/h2*15-18H,1-14H2;3*1-2H,(H,5,6)(H,7,8)/b;;3*2-1+

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C19H32N2
Molecular Weight	288.4708
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.fdanews.com/articles/102230-advisory-committee-recommends-no-approval-for-pulzium?v=preview | https://clinicaltrials.gov/ct2/show/NCT00126061 | http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con031129.pdf | https://www.ncbi.nlm.nih.gov/pubmed/14996649 | https://www.ncbi.nlm.nih.gov/pubmed/11527020

Tedisamil is an antiarrhythmic with additional anti-ischaemic properties, which acts via potassium channel blockade. This drug can be categorised as a class III antiarrhythmic agent due to its effects of action potential and QT interval prolongation in these patients. Although tedisamil has been shown to be an effective anti-ischaemic agent, with Phase III trials for angina pectoris now completed, the company are now pursuing the use of tedisamil for the treatment of atrial fibrillation, for which tedisamil is still in Phase II/III clinical trials. The FDA’s Cardiovascular and Renal Drugs Advisory Committee voted not to recommend approval for Solvay Pharmaceuticals’ investigational anti-arrhythmic drug Pulzium (Tedisamil) and asked the company to give the FDA more information.

Originator

Approval Year

PubMed

Title	Date	PubMed
Tedisamil and dofetilide-induced torsades de pointes, rate and potassium dependence.	2001 Apr	11264243
Transgenic mice overexpressing human KvLQT1 dominant-negative isoform. Part II: Pharmacological profile.	2001 May	11334836
Tedisamil and lidocaine enhance each other's antiarrhythmic activity against ischaemia-induced arrhythmias in rats.	2003 Aug	12922925
Modulation of intracellular Ca(2+) concentration by tedisamil, a class III antiarrhythmic agent, in isolated heart preparation.	2003 Aug 22	12888119
Tedisamil in coronary disease: additional benefits in the therapy of atrial fibrillation?	2003 Jun	12746750
Trials of new antiarrhythmic drugs for maintenance of sinus rhythm in patients with atrial fibrillation.	2004	14739742
Effect of the antifibrillatory compound tedisamil (KC-8857) on transmembrane currents in mammalian ventricular myocytes.	2004 Dec	15579009
Tedisamil: a new novel antiarrhythmic.	2004 Feb	14996649
Theoretical possibilities for the development of novel antiarrhythmic drugs.	2004 Jan	14754422
Safety and efficacy of intravenously administered tedisamil for rapid conversion of recent-onset atrial fibrillation or atrial flutter.	2004 Jul 7	15234416
Tedisamil attenuates foetal transformation of myosin in the hypertrophied rat myocardium.	2004 Nov	15466442
Electrical storms in Brugada syndrome: review of pharmacologic and ablative therapeutic options.	2005 Jan 1	16943940
Do we need pharmacological therapy for atrial fibrillation in the ablation era?	2006 Dec	17340189
Approach to the asymptomatic patients with Brugada syndrome.	2007 Apr 1	17538698
New antiarrhythmic treatment of atrial fibrillation.	2007 Jul	17605649
Update on atrial fibrillation: part II.	2008 Mar	18383050
New horizons in antiarrhythmic therapy: will novel agents overcome current deficits?	2008 Sep 22	18790110
Recent advances in pharmacotherapy of atrial fibrillation.	2009 Aug	20523864
The transmembrane beta-subunits KCNE1, KCNE2, and DPP6 modify pharmacological effects of the antiarrhythmic agent tedisamil on the transient outward current Ito.	2009 Jun	19153714

Sample Use Guides

In Vivo Use Guide

The recommended dose is 0.32 mg/kg

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:04:28 UTC 2023` Edited by `admin` on `Fri Dec 15 16:04:28 UTC 2023`
Record UNII	Y4HRG433UU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEDISAMIL SESQUIFUMARATE

Official Name

English

KC-8857 SESQUIFUMARATE

Code

English

TEDISAMIL SESQUIFUMARATE [USAN]

Common Name

English

Tedisamil sesquifumarate [WHO-DD]

Common Name

English

PULZIUM

Brand Name

English

SPIRO(CYCLOPENTANE-1,9'-(3,7)DIAZABICYCLO(3.3.1)NONANE), 3',7'-BIS(CYCLOPROPYLMETHYL)-, (2E)-2-BUTENEDIOATE (2:3)

Common Name

English

TEDISAMIL SESQUIFUMARATE [MI]

Common Name

English

BIS(3',7'-BIS(CYCLOPROPYLMETHYL)SPIRO(CYCLOPENTANE-1,9'-(3,7)DIAZABICYCLO(3.3.1)NONANE))DIHYDROGEN TRIS((2E-BUT-2-ENEDIOATE)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C93038