Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H26NO2 |
| Molecular Weight | 288.4045 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 1 |
SHOW SMILES / InChI
SMILES
CC(C)[N+](C)(C)CC(O)COC1=C2C=CC=CC2=CC=C1
InChI
InChIKey=VOPWPUXOWBDNBN-UHFFFAOYSA-N
InChI=1S/C18H26NO2/c1-14(2)19(3,4)12-16(20)13-21-18-11-7-9-15-8-5-6-10-17(15)18/h5-11,14,16,20H,12-13H2,1-4H3/q+1
Pranolium (UM-272) is propranolol derivative. It can reduce the extent of myocardial injury sustained during severe ischemia. UM-272 lacks significant beta-adrenergic blocking activity but retains the negative chronotropic, negative inotropic and antiarrhythmic effects common to both d- and l-propranolol. The protective effects of UM-272 during myocardial ischemia cannot be due to metabolic effects of the beta-adrenergic blockade but may be due to effects on oxygen consumption or to effects on myocardial membrane properties that are related to its antiarrhythmic and myocardial depressant activity. The ability of UM-272 to enhance blood flow to subendocardial myocardium may also play a role in its beneficial effects during ischemia. UM-272 may protect the ischemic heart through direct effects on myocardial Ca++ regulating mechanisms. UM-272 has kinetically similar use-dependent inhibitory action of the fast sodium channels of cardiac muscles as other Class Ia antiarrhythmic drugs like quinidine or procainamide. Pranolium was investigated as an antiarrhythmic agent.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Membrane antiperoxidative activities of D-propranolol, L-propranolol and dimethyl quaternary propranolol (UM-272). | 1992-01 |
|
| [Synthesis and pharmacologic properties of pranolium and its optical isomers]. | 1990-03 |
|
| Involvement of brain transmitters in the modulation of shock-induced aggression in rats by propranolol and related drugs. | 1987-02 |
|
| Autonomic regulation involved in the ocular hypotensive action of beta-adrenergic blocking agents. | 1986-04 |
|
| [Effects of pranolium on action potentials of myocardiac cells and on aconitine-induced arrhythmias]. | 1985-12 |
|
| AQ-AH 208, a new bradycardic agent, increases coronary collateral blood flow to ischemic myocardium. | 1985-11-01 |
|
| Effects of dimethylpropranolol (UM-272) on the electrophysiological properties of guinea-pig ventricular muscles. | 1985-08 |
|
| Alterations in isoproterenol-induced cardiac metabolic changes by a quaternary analog of propranolol, UM-272. | 1985 |
|
| Role of vagus in the antagonism of ouabain induced arrhythmias in dogs by beta-adrenoceptor antagonists and related drugs. | 1984-10 |
|
| In vivo and in vitro studies of bacterial endotoxin-membrane interactions and the effects of membrane-active agents. | 1984-09 |
|
| Effects of three bradycardiac drugs on regional myocardial blood flow and function in areas distal to a total or partial coronary occlusion in dogs. | 1984-02 |
|
| Mechanism of action of dimethyl quaternary propranolol (UM-272) in isoproterenol-induced cardiomyopathy in rats. | 1983-06 |
|
| Plasma acid phosphatase levels in endotoxaemia: modification by drugs and chemically detoxified endotoxins. | 1983-06 |
|
| Sublingual absorption of the quaternary ammonium antiarrhythmic agent, UM-272. | 1983 |
|
| Antiarrhythmic effects of the quaternary propranolol analog that does not induce beta-adrenergic blockade. | 1982-07 |
|
| Chronic ventricular tachyarrhythmias in the conscious dog: prevention by UM-272 (dimethylpropranolol). | 1981-07-01 |
|
| Pharmacologic protection against prolonged ischemia during harvesting and preservation of canine kidneys. | 1981-03 |
|
| Disposition of pranolium chloride in dogs, baboons and monkeys. | 1981 |
|
| Plasma and myocardial tissue concentrations of UM-272 (N,N-dimethylpropranolol) after oral administration in dogs. | 1980-08 |
|
| Electrophysiologic actions of UM-272 (Pranolium) on reentrant ventricular arrhythmias in postinfarction canine myocardium. | 1980-08 |
|
| Protective effects of dimethyl-propranolol (UM-272) during global ischemia of isolated feline hearts. | 1980-03 |
|
| Disposition of pranolium chloride in small mammals. | 1980-03 |
Patents
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50643-33-9
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DTXSID0048422
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74H68X6IUL
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38089
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ACTIVE MOIETY
