Dihydropyridines

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Chapter: Medicinal Chemistry : Antianginals

Antianginals:Dihydropyridines : i. Verapamil ii. Diltiazem - Structure, Properties, uses, Synthesis, Assay, Storage, Dosage forms, Dose


SYNTHESIS AND DRUG PROFILE

i. Verapamil


Synthesis

Step I. Synthesis of 3,4-Dimethoxy-2-isopropyl valeronitrile


Step II. Preparation of 3,4 Dimethoxy phenyl ethyl N-methyl-3-chloro propylamine


Step III. Condensation of product of Step I and II


Properties and uses: It is a white crystalline powder, soluble in water, freely soluble in methanol, and sparingly soluble in alcohol. It is used in the treatment of angina pectoris, arrhythmias from ischaemic myocardial syndromes, and supraventricular arrhythmias.

Assay: Dissolve the sample in ethanol and add 0.01 M hydrochloric acid. Titrate with 0.1 M sodium hydroxide and determine the end point potentiometrically.

Storage: It should be stored in well-closed airtight containers and protected from light.

Dosage forms: Verapamil HCl injection I.P., Verapamil HCl tablets I.P., Verapamil injection B.P., Verapamil tablets B.P., Prolonged-release Verapamil tablets B.P.


ii. Diltiazem


Synthesis


Properties and uses: It is a white crystalline powder, freely soluble in water, in methanol, and in methylene chloride, slightly soluble in ethanol. Diltiazem has two chiral centres (C2 and C3), the levorotatory cis antipode is more active form. It is used in the treatment of angina pectoris and also used as antiarrhythmic agent.

Assay: Dissolve the sample in a mixture of anhydrous formic acid and acetic anhydride. Titrate with 0.1 M perchloric acid and determine the end point potentiometrically.

Storage: It should be stored in well-closed airtight containers and protected from light.


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