Nilvadipine

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
Nilvadipine Structure
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.
Safety Information
Hazard Codes Xn
Risk Statements 22
WGK Germany 3
RTECS US7968300
HS Code 2933.39.9200
ToxicityLD50 oral in rat: 1560mg/kg
MSDS Information
Nilvadipine Usage And Synthesis
DescriptionNilvadipine 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 PropertiesYellow Prisms
OriginatorFujisawa (Japan)
UsesUsed as an antihypertensive and antianginal.
Usesantihypertensive;calcium channel blocker
DefinitionChEBI: Nilvadipine is an isopropyl ester, a methyl ester, a nitrile and a dihydropyridine.
Manufacturing ProcessTo 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 nameNivadil
Therapeutic FunctionCalcium entry blocker, Antihypertensive
References1) 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
Methylparaben Methyl Propyl gallate ISOPROPYL LAURATE Nitrendipine Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate Nisoldipine M-NIFEDIPINE Tribenuron methyl 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester Isopropyl acetate (S)-(-)-Nilvadipine,(S)-Nilvadipine Methanol Isopropyl alcohol Cyano Propyl acetate Dihydromyrcenol Nilvadipine

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