Nilvadipine is a new, second-generation calcium channel blocker effective in the
treatment of hypertension and angina pectoris. Its potent inhibitory effect on the
stimulated chemotaxis of smooth muscle cells and protective action against calcium
deposition suggest that nilvadipine may be useful for preventing and treating
atherosclerosis.
Used as an antihypertensive and antianginal.
antihypertensive;calcium channel blocker
ChEBI: Nilvadipine is an isopropyl ester, a methyl ester, a nitrile and a dihydropyridine.
To a solution of isopropyl ester of 6-formyl-5-methoxycarbonyl-2-methyl-4-(3-
nitrophenyl)-1,4-dihydropyridine- 3-carboxylic acid (4.5 g) in acetic acid (35
ml) were added hydroxylamine hydrochloride (0.97 g) and sodium acetate
(1.43 g), and the mixture was stirred at ambient temperature for 2.5 hours.
After acetic anhydride (4.14 g) was added to this reaction mixture, the
mixture was stirred at ambient temperature for 1.5 hours and at 95-100°C for
additional 4 hours. The acetic acid and the excess of acetic anhydride were
removed in vacuum, followed by adding water to the residue and it was
neutralized with a saturated aqueous solution of sodium bicarbonate. This
aqueous suspension was extracted twice with ethyl acetate, and the combined
extract was washed with water, dried over anhydrous magnesium sulfate and
evaporated to dryness under reduced pressure to give a reddish-brown oil
(4.88 g), which was chromatographed over silica gel (150 g) with a mixture of benzene and ethyl acetate (10:1 by volume) as an eluent to give a crude
crystals (2.99 g). These were recrystallized from ethanol to give yellow prisms
(1.89 g) of isopropyl ester of 6-cyano-5-methoxycarbonyl-2-methyl-4-(3-
nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid melting point 148-150°C
(yellow prisms from ethanol); [α]D20 = 222.4° (c = 1 in methanol).
Calcium entry blocker, Antihypertensive
1) Paris?et al. (2014),?The spleen tyrosine kinase (Syk) regulates Alzheimer amyloid-β production and Tau hyperphosphorylation; J. Biol. Chem.,?289?33927
2) Rosenthal (1994),?Nilvadipine: profile of a new calcium antagonist. An overview; J. Cardiovasc. Pharmacol. 24 Suppl 2?S92
3) Nimmrich and Eckert (2013),?Calcium channel blockers and dementia; Br. J. Pharmacol.?169?1203
4) Otori?et al. (2003),?Protective effect of nilvadipine against glutamate neurotoxicity in purified retinal ganglion cells; Brain Res.?961?213
