Procainamid

procainamide Struktur
51-06-9
CAS-Nr.
51-06-9
Bezeichnung:
Procainamid
Englisch Name:
procainamide
Synonyma:
C07401;Procamide;Novocamid;Procainamide;Novocainamide;PROCAINEAMIDE;Novocaine amide;procainamide USP/EP/BP;procainamide Solution, 100ppm;4-Amino-N-(2-diethylaminoethyl)
CBNumber:
CB5932746
Summenformel:
C13H21N3O
Molgewicht:
235.33
MOL-Datei:
51-06-9.mol

Procainamid Eigenschaften

Schmelzpunkt:
47°C
Siedepunkt:
377.72°C (rough estimate)
Dichte
1.060
Brechungsindex
1.5700 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
Chloroform (Slightly), Ethyl Acetate (Slightly)
Aggregatzustand
Solid
pka
pKa 9.24±0.10 (Uncertain)
Farbe
Off-White to Light Brown

Sicherheit

RIDADR  2811
HazardClass  6.1
PackingGroup 
Giftige Stoffe Daten 51-06-9(Hazardous Substances Data)

Procainamid Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Procainamide and its analogs were employed by Dr Claude Beck in a series of cardiac surgeries during the early 1930s. The compound was used to alleviate arrhythmias that present during the procedures, and was selected for its favorable tissue absorption properties. Procainamide’s central amide provides it protection from inactivating esterase action and allows oral administration of the compound. Procainamide was approved for use in the United States in 1950.

Verwenden

Procainamide is intended for treating paroxysmal atrial tachycardia, atrial fibrillation, premature ventricular contraction, and ventricular tachycardia. For quickly reaching therapeutic concentrations, parenternal introduction of procainamide is preferred over cynidine.

Definition

ChEBI: 4-Aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.

Biologische Funktion

Procainamide (Pronestyl, Procan SR) is a derivative of the local anesthetic agent procaine. Procainamide has a longer half-life, does not cause CNS toxicity at therapeutic plasma concentrations, and is effective orally. Procainamide is a particularly useful antiarrhythmic drug, effective in the treatment of supraventricular, ventricular, and digitalis-induced arrhythmias.

Mechanism of action

The chemical difference between procainamide and procaine lies in the replacement of the ester group with an amide group. The action of procainamide is qualitatively similar to the action of procaine. Its effect on the heart is identical to that of quinidine. As an antiarrhythmic, procainamide is preferred over procaine because unlike procaine, it is better absorbed when taken orally and it is more difficult for the esterases of the plasma to hydrolyze it, which results in long-lasting action.

Clinical Use

Procainamide is an effective antiarrhythmic agent when given in sufficient doses at relatively short (3–4 hours) dosage intervals. Procainamide is useful in the treatment of premature atrial contractions, paroxysmal atrial tachycardia, and atrial fibrillation of recent onset. Procainamide is only moderately effective in converting atrial flutter or chronic atrial fibrillation to sinus rhythm, although it has value in preventing recurrences of these arrhythmias once they have been terminated by direct current (DC) cardioversion.
Procainamide can decrease the occurrence of all types of active ventricular dysrhythmias in patients with acute myocardial infarction who are free from A-V dissociation, serious ventricular failure, and cardiogenic shock. About 90% of patients with ventricular premature contractions and 80% of patients with ventricular tachycardia respond to procainamide administration. Although the spectrum of action and electrophysiological effects of quinidine and procainamide are similar, the relatively short duration of action of procainamide has tended to restrict its use to patients who are intolerant of or unresponsive to quinidine.

Nebenwirkungen

Acute cardiovascular reactions to procainamide administration include hypotension, A-V block, intraventricular block, ventricular tachyarrhythmias, and complete heart block. The drug dosage must be reduced or even stopped if severe depression of conduction (severe prolongation of the QRS interval) or repolarization (severe prolongation of the QT interval) occurs.
Long-term drug use leads to increased antinuclear antibody titers in more than 80% of patients; more than 30% of patients receiving long-term procainamide therapy develop a clinical lupus erythematosus–like syndrome. The symptoms may disappear within a few days of cessation of procainamide therapy, although the tests for antinuclear factor and lupus erythematosus cells may remain positive for several months.
Procainamide, unlike procaine, has little potential to produce CNS toxicity. Rarely, patients may be confused or have hallucinations.

Arzneimittelwechselwirkung

The inherent anticholinergic properties of procainamide may interfere with the therapeutic effect of cholinergic agents. Patients receiving cimetidine and procainamide may exhibit signs of procainamide toxicity, as cimetidine inhibits the metabolism of procainamide. Simultaneous use of alcohol will increase the hepatic clearance of procainamide. Procainamide may enhance or prolong the neuromuscular blocking activity of the aminoglycosides with the potential of producing respiratory depression. The simultaneous administration of quinidine or amiodarone may increase the plasma concentration of procainamide.

Stoffwechsel

Metabolites of procainamide include p-aminobenzoic acid and N-acetylprocainamide. Interestingly, the acetylated metabolite is also active as an antiarrhythmic. Its formation accounts for up to one-third of the administered dose and is catalyzed by the liver enzyme N-acetyl transferase. Because acetylation is strongly influenced by an individual's genetic background, marked variability in the amounts of this active metabolite may be observed from patient to patient. Renal excretion dominates, with approximately 90% of a dose excreted as unchanged drug and metabolites. The elimination half-life is approximately 3.5 hours. A substantial percentage (60–70%) of patients on procainamide show elevated levels of antinuclear antibodies after a few months. Of these patients, between 20 and 30% develop a drug-induced lupus syndrome if therapy is continued. These adverse effects, which are attributed to the aromatic amino group, are observed more frequently and more rapidly in “slow acetylators.” Usually, the symptoms associated with procainamide-induced lupus syndrome subside fairly rapidly after the drug is discontinued. These problems, however, have discouraged long-term procainamide therapy.

Vorsichtsmaßnahmen

Contraindications to procainamide are similar to those for quinidine. Because of its effects on A-V nodal and His-Purkinje conduction, procainamide should be administered with caution to patients with second-degree A-V block and bundle branch block. Procainamide should not be administered to patients who have shown procaine or procainamide hypersensitivity and should be used with caution in patients with bronchial asthma. Prolonged administration should be accompanied by hematological studies, since agranulocytosis may occur.

Procainamid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Procainamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 75)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28180 58
Alchem Pharmtech,Inc.
8485655694
sales@alchempharmtech.com United States 63711 58
career henan chemical co
+86-0371-86658258 15093356674;
factory@coreychem.com China 29826 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167
1026@dideu.com China 9802 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250
1026@dideu.com China 29831 58
Finetech Industry Limited
+86-27-87465837 +8618971612321
info@finetechnology-ind.com China 9589 58
ZHEJIANG JIUZHOU CHEM CO., LTD
+86-0576225566889 +86-13454675544
admin@jiuzhou-chem.com;jamie@jiuzhou-chem.com;alice@jiuzhou-chem.com China 20000 58
LEAPCHEM CO., LTD.
+86-852-30606658
market18@leapchem.com China 43348 58
Energy Chemical 021-021-58432009 400-005-6266
sales8178@energy-chemical.com China 44751 61
Beijing HuaMeiHuLiBiological Chemical 010-56205725
waley188@sohu.com China 12338 58

51-06-9(Procainamid)Verwandte Suche:


  • PROCAINEAMIDE
  • Novocainamide
  • Novocaine amide
  • Novocamid
  • Procamide
  • Procainamide
  • 4-Amino-N-[2-(diethylamino)ethyl]benzamide
  • C07401
  • 4-Amino-N-(2-diethylaminoethyl)
  • procainamide USP/EP/BP
  • Benzamide, 4-amino-N-[2-(diethylamino)ethyl]-
  • procainamide Solution, 100ppm
  • 51-06-9
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