22059-60-5 Usage
Description
Disopyramid phosphate, also known as -[2(diisopropylamino)ethyl]-phenyl-2-pyridineacetamidephosphate (Norpace), is an oral and intravenous class IA antiarrhythmic agent. It is structurally similar to quinidine and procainamide, possessing electrophysiological properties that include decreasing phase 4 diastolic depolarization, reducing conduction velocity, and exhibiting vagolytic properties. Disopyramid phosphate is primarily used in the treatment of refractory, life-threatening ventricular tachyarrhythmias. It is administered orally, with peak plasma levels achieved within 2 hours, and has a half-life of 6.7 hours in humans. The drug is bound to approximately 50% of plasma proteins and is excreted in more than 50% of its unchanged form in the urine. Due to its structural similarity to anticholinergic drugs, it commonly exhibits side effects such as dry mouth, constipation, urinary retention, and other cholinergic blocking actions. Patients with renal insufficiency should be carefully monitored for signs of overdose.
Uses
Used in Pharmaceutical Industry:
Disopyramid phosphate is used as an antiarrhythmic agent for the treatment of refractory, life-threatening ventricular tachyarrhythmias. It functions as a sodium channel blocker, which helps in stabilizing the heart rhythm.
Used in Research and Analysis:
Disopyramid phosphate salt has been utilized as an internal standard for plasma sample analysis by mass spectrometry, ensuring accurate and reliable results in various studies.
Used in Toxicology Studies:
It might be used as a test compound in teratogenicity studies, which are crucial for understanding the potential risks and effects of drugs on fetal development.
Used in Cardiology:
As a cardiac depressant, disopyramid phosphate is employed in the management of life-threatening arrhythmias, providing a crucial therapeutic option for patients with severe heart rhythm disorders.
Originator
Rythmodan,Cassenne,France,1969
Manufacturing Process
To a solution of 35.3 parts of phenylacetonitrile and 47.6 parts of 2-
bromopyridine in 175 parts of dry toluene is added 53.4 parts of sodamide
slowly with stirring over a period of 45 minutes. The resultant mixture is
stirred at 100°C for 2 hours before it is cooled and the excess sodamide is
decomposed by the addition of water. The toluene layer is separated and
washed with water to remove excess alkali. The toluene solution is extracted
with 6 N hydrochloric acid and the acid extract is made alkaline and then
extracted with toluene. The toluene solution is dried over sodium sulfate and
the solvent is evaporated. Recrystallization of the residue from alcohol-hexane
gives α-phenyl-2-pyridineacetonitrile melting at about 87-88°C.To a solution of 41 parts of α-phenyl-2-pyridineacetonitrile in 350 parts of dry
toluene is added 9.2 parts of sodamide and the mixture is stirred and heated
at 90°C for 30 minutes. Heating is stopped and a solution of 38.5 parts of 2-
diisopropylaminoethyl chloride in 110 parts of dry toluene is added slowly over
a period of 30 minutes. The mixture is stirred and refluxed for 6 hours before
it is cooled and decomposed by the addition of water. The toluene layer is
separated and washed with water and extracted with 6 N hydrochloric acid.
The acid extract is made alkaline and extracted with toluene. The toluene
solution is washed with water and dried and the solvent is evaporated.
Distillation of the residue gives 4-diisopropylamino-2-phenyl-2-(2-pyridyl)-
butyronitrile boiling at about 145°-160°C at 0.3 mm pressure.A solution of 27.2 parts of 4-diisopropylamino-2-phenyl-2-(2-
pyridyl)butyronitrile in 200 parts of concentrated sulfuric acid is heated on a
steam bath for 4 hours and then poured onto ice. The resultant mixture is
alkalized with 10 N sodium hydroxide, and the pH is adjusted to 6 by the
addition of acetic acid. The solution is washed once with benzene before it is
alkalized again with 10 N sodium hydroxide solution. The resultant mixture is
extracted with benzene, and the solvent is evaporated from the benzene
extract. The resultant residue is dissolved in ethanol and the alcohol solution
is treated with charcoal and filtered. Evaporation of the solvent leaves a
residue which is recrystallized from hexane to give 4-diisopropylamino-2-
phenyl-2-(2-pyridyl)butyramide melting at about 94.5-95°C. It may be
converted to the phosphate with phosphoric acid.
Therapeutic Function
Antiarrhythmic
Biochem/physiol Actions
Class IA antiarrhythmic; sodium channel blocker
Check Digit Verification of cas no
The CAS Registry Mumber 22059-60-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,0,5 and 9 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 22059-60:
(7*2)+(6*2)+(5*0)+(4*5)+(3*9)+(2*6)+(1*0)=85
85 % 10 = 5
So 22059-60-5 is a valid CAS Registry Number.
InChI:InChI=1/C21H29N3O.H3O4P/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19;1-5(2,3)4/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25);(H3,1,2,3,4)
