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P4670

Sigma-Aldrich

Propafenone hydrochloride

Synonym(s):

1-[2-(2-Hydroxy-3-(propylamino)propoxy)phenyl]-3-phenyl-1-propanone hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C21H27NO3 · HCl
CAS Number:
34183-22-7
Molecular Weight:
377.90
EC Number:
251-867-9
MDL number:
MFCD00079243
UNSPSC Code:
41116107
PubChem Substance ID:
24278636
NACRES:
NA.77

form

powder

originator

Abbott

storage temp.

2-8°C

SMILES string

Cl[H].CCCNCC(O)COc1ccccc1C(=O)CCc2ccccc2

InChI

1S/C21H27NO3.ClH/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17;/h3-11,18,22-23H,2,12-16H2,1H3;1H

InChI key

XWIHRGFIPXWGEF-UHFFFAOYSA-N

Gene Information

human ... ABCB1(5243) , ADRB1(153) , ADRB2(154) , ADRB3(155) , CYP1A2(1544) , SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)

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General description

Propafenone hydrochloride is a calcium antagonist. It functions as a Na+ and K+ channel blocker. It might be used to treat patients with systemic hypertension. Propafenone hydrochloride is associated with bradycardia and bronchospasms. It is metabolized in the liver. Propafenone hydrochloride is used to treat ventricular arrhythmias.

Application

Propafenone hydrochloride has been used in the isolation of cardiomyocytes.

Biochem/physiol Actions

Blocks hKv1.5 and ATP-sensitive K+ channels; class 1C antiarrhythmic agent that is also an antagonist at β adrenergic receptors.

Features and Benefits

This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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L Franqueza et al.
British journal of pharmacology, 125(5), 969-978 (1998-12-10)
1. The goal of this study was to analyse the effects of propafenone and its major metabolite, 5-hydroxy-propafenone, on a human cardiac K+ channel (hKv1.5) stably expressed in Ltk- cells and using the whole-cell configuration of the patch-clamp technique. 2.
Lambert K Sørensen
Journal of analytical toxicology, 36(2), 116-122 (2012-02-18)
A liquid chromatography-tandem mass spectrometry method, using pneumatically assisted electrospray ionization was developed for the determination of amiodarone, desethylamiodarone, propafenone, N-depropylpropafenone, 5-OH-propafenone, flecainide, and sotalol in human antemortem and postmortem whole blood. A mixture of methanol and acetonitrile was used
David Lowes et al.
Journal of medicinal chemistry, 55(13), 6087-6093 (2012-06-20)
Previously reported studies identified analogues of propafenone that had potent antimalarial activity, reduced cardiac ion channel activity, and properties that suggested the potential for clinical development for malaria. Careful examination of the bioavailability, pharmacokinetics, toxicology, and efficacy of this series
David J Lowes et al.
Journal of medicinal chemistry, 54(21), 7477-7485 (2011-10-01)
Propafenone, a class Ic antiarrythmic drug, inhibits growth of cultured Plasmodium falciparum. While the drug's potency is significant, further development of propafenone as an antimalarial would require divorcing the antimalarial and cardiac activities as well as improving the pharmacokinetic profile
G Christé et al.
European journal of pharmacology, 373(2-3), 223-232 (1999-07-22)
Propafenone, a class I antiarrhythmic agent, inhibits several membrane currents (I(Na), I(Ca), I(K), Ito), however, its effects on ATP-sensitive potassium current (I(K)ATP) of cardiac cells have not been tested. We evaluated the blocking effects of 0.1 to 100 microM propafenone
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