Nicardipine Chemical Properties

Melting point:

136-138 °C

Boiling point:

603.4±55.0 °C(Predicted)

Density 

1.230±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Dichloromethane; Methanol

form 

Solid

pka

7.30±0.50(Predicted)

color 

Yellow

CAS DataBase Reference

55985-32-5(CAS DataBase Reference)

Nicardipine Usage And Synthesis

Originator

Nicodel,Mitsui,Japan,1981

Uses

Vasodilator.

Uses

It is used for arterial hypertension, chronic, stable angina pectoris, preventing angina pectoris, and for ischemic-type abnormalities of brain blood flow.

Uses

Nicardipine is a dihydropyridine calcium channel blocker. Antianginal; antihypertensive. Neuroprotective & Neuroresearch products.

Definition

ChEBI: Nicardipine is a racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension. It has a role as an antihypertensive agent, a calcium channel blocker, a vasodilator agent and an autophagy inhibitor. It contains a (S)-nicardipine and a (R)-nicardipine.

Manufacturing Process

A mixture of 4.98 g of acetoacetic acid N-benzyl-N-methylaminoethyl ester, 2.3 g of β-aminocrotonic acid methyl ester, and 3 g of m-nitrobenzaldehyde was stirred for 6 hours at 100°C in an oil bath. The reaction mixture was subjected to a silica gel column chromatography (diameter 4 cm and height 25 cm) and then eluted with a 20:1 mixture of chloroform and acetone. The effluent containing the subject product was concentrated and checked by thin layer chromatography. The powdery product thus obtained was dissolved in acetone and after adjusting the solution with an ethanol solution saturated with hydrogen chloride to pH 1-2, the solution was concentrated to provide 2 g of 2,6-dimethyl-4-(3'-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylic acid 3-methylester-5-β-(N-benzyl-N-methylamino)ethyl ester hydrochloride. The product thus obtained was then crystallized from an acetone mixture, melting point 136°C to 140°C (decomposed).

brand name

Cardene(PDL Biopharma); Cardene (Roche).

Therapeutic Function

Vasodilator

Mechanism of action

Nicardipin relaxes smooth musculature of vessels, lowers resistance of coronary and peripheral vessels, increases blood flow in vessels of the brain, causes a moderate and stable hypotensive effect, and reduces the myocardial need for oxygen.

Synthesis

Nicardipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-methyl-2-[(methylphenylmethyl)- amino]ethyl ester 3,5-pirididincarboxylic acid (19.3.7), is synthesized in a manner analogous to the synthesis of nifedipine, the only difference being that in the Hantsch synthesis, two different |?-dicarbonyl compounds are used simultaneously with o-nitrobenzaldehyde. During this, one of these in the enamine form of acetoacetic ester is simultaneously used as an amine component. A heterocyclization reaction is accomplished by reacting, the methyl ester of |?-aminocrotonic acid with the 2-methyl-2-benzylaminoethyl ester of acetoacetic acid.

Nicardipine(55985-32-5)Related Product Information

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