Nicardipine

Nicardipine Basic information
Product Name:Nicardipine
Synonyms:1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-[methy(phenyl-methyl)amino]ethyl ester hydrochloride;Nicardipine (base and/or unspecified salts);Methyl 2-(benzyl-methyl-amino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-[2-[methyl(benzyl)amino]ethyl]5-methyl ester;NicardipineBase;Nicardipine Hcl 54527-84-3 / Base;2-(benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate;benzylmethylamino)ethylmethylester
CAS:55985-32-5
MF:C26H29N3O6
MW:479.52
EINECS:259-932-3
Product Categories:Active Pharmaceutical Ingredients
Mol File:55985-32-5.mol
Nicardipine Structure
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
pka7.30±0.50(Predicted)
form Solid
color Yellow
CAS DataBase Reference55985-32-5(CAS DataBase Reference)
Safety Information
MSDS Information
Nicardipine Usage And Synthesis
OriginatorNicodel,Mitsui,Japan,1981
UsesVasodilator.
UsesIt is used for arterial hypertension, chronic, stable angina pectoris, preventing angina pectoris, and for ischemic-type abnormalities of brain blood flow.
UsesNicardipine is a dihydropyridine calcium channel blocker. Antianginal; antihypertensive. Neuroprotective & Neuroresearch products.
DefinitionChEBI: 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 ProcessA 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 nameCardene(PDL Biopharma); Cardene (Roche).
Therapeutic FunctionVasodilator
Mechanism of actionNicardipin 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.
SynthesisNicardipine, 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.

Synthesis_55985-32-5

Barnidipine Chlorodimethylphenylsilane NICARDIPINE HYDROCHLORIDE,NICARDIPINE HCL,NICARDIPINE HYDROCHLORIDE (YC-93) CALCIU M CHANNEL ANTAG,NICARDIPINE HYDROCHLORIDE MM(CRM STANDARD) Barnidipine Benidipine Nicardipine N,N-Dimethylformamide Poly(dimethylsiloxane) Benzyl alcohol ETHANE Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate Dehydro Nicardipine Hydrochloride Dimethyl fumarate Dimethyl sulfoxide Benzyl Dimethyl ether Dimethyl carbonate Dimethyl sulfate

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