Propafenone

Structural formula
	Structural formula without stereochemistry
General
Surname	Propafenone
other names	( RS ) -1- {2- [2-Hydroxy-3- (propylamino) propoxy] phenyl} -3-phenylpropan-1-one; (±) -1- {2- [2-Hydroxy-3- (propylamino) propoxy] phenyl} -3-phenylpropan-1-one; rac -1- {2- [2-hydroxy-3- (propylamino) propoxy] phenyl} -3-phenylpropan-1-one;
Molecular formula	C 21 H 27 NO 3
External identifiers / databases
EC number	258-955-6
ECHA InfoCard	100.053.578
PubChem	4932
ChemSpider	4763
DrugBank	DB01182
Wikidata	Q662511
Drug information
ATC code	C01 BC03
Drug class	Antiarrhythmic
Mechanism of action	Class IC - sodium channel blockers
properties
Molar mass	341.44 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	700 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propafenone is a drug from the group of antiarrhythmics that is used in the treatment of cardiac arrhythmias . According to the classification by E. Vaughan Williams, propafenone belongs to class I of antiarrhythmics (sodium channel blockers), more precisely (together with flecainide ) to class IC.

Clinical information

Propafenone is used (intravenously at 0.5 to 1 mg / kg) among other things for ventricular tachycardia and ventricular extrasystoles. It can also be used for atrial fibrillation (with tachyarrhythmia absoluta).

Pharmacological properties

Mechanism of action (pharmacodynamics)

Propafenone binds to cardiac sodium channels , the protein binding here is over 90%. Due to a comparatively long binding time, propafenone is also effective at rest frequency. In contrast to other representatives of the drug class, it hardly influences the duration of the action potential, but strongly blocks the rapid sodium influx of phase 0 ( QRS expansion in the resting frequency range). Because propafenone is structurally related to beta blockers , it also has lidocaine and quinidine- like effects and can also block calcium channels and β channels. Docking on ATP-sensitive potassium channels in cardiac muscle cells is to be regarded as undesirable .

Absorption and distribution in the body (pharmacokinetics)

Enteral absorption is good, but bioavailability is limited (approx. 50%) due to a first-pass effect . The plasma half-life is 3–6 hours.

Stereochemistry

Propafenone contains a stereocenter and consists of two enantiomers. This is a racemate , i.e. a 1: 1 mixture of ( R ) - and ( S ) -form:

Enantiomers of propafenone
CAS number: 107381-31-7	CAS number: 107381-32-8

Trade names

Monopreparations

Rytmonorm (D, CH) and Cuxafenon (D).

Individual evidence

↑ ^a ^b ^c data sheet Propafenone hydrochloride from Sigma-Aldrich , accessed on May 17, 2014 ( PDF ).
↑ E. Vaughan Williams: Classification of anti-arrhythmic drugs In: Symposium on Cardiac Arrhythmias , Sandfte E, Flensted-Jensen E, Olesen KH eds. Sweden, AB ASTRA, Södertälje, 1970 449-472.
↑ ^a ^b Ernst Mutschler, Monika Schäfer-Korting a. a .: Textbook of pharmacology and toxicology . 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001. ISBN 3-8047-1763-2 , pp. 549ff
↑ HM Bryson, KJ Palmer et al. a .: propafenone. A reappraisal of its pharmacology, pharmacokinetics and therapeutic use in cardiac arrhythmias. In: Drugs , 1993 , 45 (1)
↑ Reinhard Larsen: Anesthesia and intensive medicine in cardiac, thoracic and vascular surgery. (1st edition 1986) 5th edition. Springer, Berlin / Heidelberg / New York et al. 1999, ISBN 3-540-65024-5 , p. 75.
^ A. Sestito, E. Molina: Atrial fibrillation and the pharmacological treatment: the role of propafenone. In: European Review for Medical and Pharmacological Sciences , 2012 , 16 (2); 242-253.
↑ G Christé, H Tebbakh, M Simurdová, R Forrat, J Simurda: Propafenone blocks ATP-sensitive K + channels in rabbit atrial and ventricular cardiomyocytes. In: European Journal of Pharmacology . 1999 4; 373 (2-3): 223-232.
↑ F. v. Bruchhausen, G. Dannhardt, S. Ebel, AW Frahm, E. Hackenthal, U. Holzgrabe (Eds.): Hagers Handbook of Pharmaceutical Practice: Volume 9: Material PZ , Springer Verlag, Berlin, Edition 5, 2014, p. 387, ISBN 978-3-642-63389-8 .
↑ Compendium.ch: Specialist information , online here ; last accessed on 9 October 2018

[Sigma-Aldrich-1] ta sheet Propafenone hydrochloride from Sigma-Aldrich , accessed on May 17, 2014 ( PDF ).

[2] E. Vaughan Williams: Classification of anti-arrhythmic drugs In: Symposium on Cardiac Arrhythmias , Sandfte E, Flensted-Jensen E, Olesen KH eds. Sweden, AB ASTRA, Södertälje, 1970 449-472.

[Mutschler-3] Ernst Mutschler, Monika Schäfer-Korting a. a .: Textbook of pharmacology and toxicology . 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001. ISBN 3-8047-1763-2 , pp. 549ff

[4] HM Bryson, KJ Palmer et al. a .: propafenone. A reappraisal of its pharmacology, pharmacokinetics and therapeutic use in cardiac arrhythmias. In: Drugs , 1993 , 45 (1)

[5] Reinhard Larsen: Anesthesia and intensive medicine in cardiac, thoracic and vascular surgery. (1st edition 1986) 5th edition. Springer, Berlin / Heidelberg / New York et al. 1999, ISBN 3-540-65024-5 , p. 75.

[6] A. Sestito, E. Molina: Atrial fibrillation and the pharmacological treatment: the role of propafenone. In: European Review for Medical and Pharmacological Sciences , 2012 , 16 (2); 242-253.

[7] G Christé, H Tebbakh, M Simurdová, R Forrat, J Simurda: Propafenone blocks ATP-sensitive K + channels in rabbit atrial and ventricular cardiomyocytes. In: European Journal of Pharmacology . 1999 4; 373 (2-3): 223-232.

[Hager-8] F. v. Bruchhausen, G. Dannhardt, S. Ebel, AW Frahm, E. Hackenthal, U. Holzgrabe (Eds.): Hagers Handbook of Pharmaceutical Practice: Volume 9: Material PZ , Springer Verlag, Berlin, Edition 5, 2014, p. 387, ISBN 978-3-642-63389-8 .

[9] Compendium.ch: Specialist information , online here ; last accessed on 9 October 2018