Procainamide

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Structural formula
Structural formula of procainamide
General
Non-proprietary name Procainamide
other names

4-Amino- N - (2-diethylaminoethyl) -benzamide ( IUPAC )

Molecular formula
  • C 13 H 21 N 3 O 2 (procainamide)
  • C 13 H 21 N 3 O 2 HCl (procainamide hydrochloride )
External identifiers / databases
CAS number
  • 51-06-9 (procainamide)
  • 614-39-1 (procainamide hydrochloride)
EC number 200-078-8
ECHA InfoCard 100,000,072
PubChem 4913
ChemSpider 4744
DrugBank DB01035
Wikidata Q417597
Drug information
ATC code

C01 BA02

Drug class

Antiarrhythmic

properties
Molar mass
  • 235.33 g · mol -1 (procainamide)
  • 271.79 g · mol -1 (· procainamide hydrochloride)
Melting point
  • 46-48 ° C
  • 165–169 ° C (procainamide hydrochloride)
boiling point

210–215 ° C (267 Pa )

pK s value

9.32

solubility

Water: 5050 mg l −1 at 25 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

Hydrochloride

07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 261-305 + 351 + 338
Toxicological data

1950 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 .

Procainamide is structurally related to procaine . It is an antiarrhythmic in the group of sodium channel blockers. It belongs to the class Ia antiarrhythmics according to the Vaughan / Williams classification. Procainamide is used as a reserve antiarrhythmic for therapy-resistant ventricular arrhythmias and for supraventricular arrhythmias in pre-excitation .

history

Alfred Einhorn synthesized procaine in 1905 with the intention of discovering a new reserve therapeutic for cocaine in local anesthesia . The antiarrhythmic effect of procaine was not discovered until 1936 by Frederick Mautz in Cleveland , Ohio . However, because procaine hydrolyzed too quickly, it was unsuitable for clinical use. Lester Charles Mark (born 1918) studied the related procainamide, which was introduced in 1951 for the treatment of ventricular arrhythmias. Henry Max Woske (born 1924) also proved its effectiveness against supraventricular arrhythmias in 1953.

Pharmacokinetics

Procainamide has a short plasma half-life of 2 to 4 hours and a bioavailability of approximately 80%. Since procainamide is excreted via the kidneys , a dose adjustment should be considered in case of renal insufficiency .

Pharmacodynamics

It has a weaker anticholinergic effect than quinidine . Procainamide can induce anti-nuclear antibodies (systemic lupus erythematosus ) in long-term therapy , in which case it should be discontinued immediately. Furthermore, it is possible that treatment with procainamide can cause hives , fever and agranulocytosis .

Individual evidence

  1. ↑ a b entry on procainamide. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
  2. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1333, ISBN 978-0-911910-00-1 .
  3. ↑ a b c Entry on procainamide in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ a b Data sheet Procainamide hydrochloride from Sigma-Aldrich , accessed on October 20, 2016 ( PDF ).
  5. ↑ Walter Sneader: Drug Discovery: A History . John Wiley & Sons, New York, NY 2005, ISBN 978-0-470-01552-0 , pp. 129 , urn : nbn: de: 101: 1-201412158328 .
  6. ^ Wolf-Dieter Müller-Jahncke , Christoph Friedrich , Ulrich Meyer: Medicinal history . 2., revised. and exp. Ed. Wiss. Verl.-Ges, Stuttgart 2005, ISBN 978-3-8047-2113-5 , pp. 163 .

literature

  • Herold Internal Medicine 2004
  • Karow / Lang Pharmacology and Toxicology 2003
  • Hacketal / Oberdisse Pharmacology and Toxicology 1997

Web links

  • Entry on procainamide at Vetpharm, accessed April 18, 2012.