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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 |
| 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 | | 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. |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | RTECS | US7968300 | | Toxicity | LD50 oral in rat: 1560mg/kg |
| 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 | Used as an antihypertensive and antianginal | | Uses | antihypertensive;calcium channel blocker | | 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 |
| Nilvadipine Preparation Products And Raw materials |
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