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Nilvadipine

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Nilvadipine Basic information

Product Name:
Nilvadipine
Synonyms:
  • 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-5-pyridinedicarboxylicacid
  • 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-isopropyl 5-methyl ester
  • BAY-e-6927
  • 2-Cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-methyl 5-isopropyl ester
  • 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid O5-isopropyl ester O3-methyl ester
  • 3-O-methyl 5-O-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  • O3-methyl O5-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  • 2-Cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 5-Isopropyl 3-Methyl Ester 5-Isopropyl 3-Methyl 2-Cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
CAS:
75530-68-6
MF:
C19H19N3O6
MW:
385.37
EINECS:
805-887-5
Product Categories:
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
75530-68-6.mol
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Nilvadipine Chemical Properties

Melting point:
148-150°C
Boiling point:
511.83°C (rough estimate)
Density 
1.3937 (rough estimate)
refractive index 
1.5900 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
DMSO: soluble15mg/mL, clear
form 
powder
pka
-0.81±0.70(Predicted)
color 
white to beige
Merck 
14,6545
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
US7968300
HS Code 
2933.39.9200
Toxicity
LD50 oral in rat: 1560mg/kg
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Nilvadipine Usage And Synthesis

Description

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.

Chemical Properties

Yellow Prisms

Originator

Fujisawa (Japan)

Uses

Used as an antihypertensive and antianginal.

Uses

antihypertensive;calcium channel blocker

Definition

ChEBI: Nilvadipine is an isopropyl ester, a methyl ester, a nitrile and a dihydropyridine.

Manufacturing Process

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).

brand name

Nivadil

Therapeutic Function

Calcium entry blocker, Antihypertensive

References

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

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