| Identification | Back Directory | [Name]
Nilvadipine | [CAS]
75530-68-6 | [Synonyms]
SKF-
fk235
ESCOR
ARC029
Nivadip
Nivadil
FR-34235
CL 287389
SKF-102362
Nivadipine
BAY-e-6927
Nivaldipine
NILVADIPINE
Nilvaldipine
Escor：Nivadil
dl-Nilvadipine
Nilvadipine-d4
Nilvadipine (ARC029)
3-methyl-5-(1-methylethyl)ester
2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-5-pyridinedicarboxylicacid
5-isopropyl-3-methyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
5-Isopropyl-3-methyl-2-cyano-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate
5-isopropyl 3-methyl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Isopropyl 6-cyano-5-methoxycarbonyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
O3-methyl O5-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Isopropyl-6-formyl-5-methoxycarbonyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-isopropyl 5-methyl ester
3-O-methyl 5-O-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 3-methyl 5-isopropyl ester
2-Cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-methyl 5-(1-methylethyl) ester
2-CYANO-1,4-DIHYDRO-6-METHYL-4-(3-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLIC ACID 3-METHYL 5-(1-METHYLETHYL) ESTER
3,5-Pyridinedicarboxylicacid, 2-cyano-1,4-dihydro-6-Methyl-4-(3-nitrophenyl)-, 3-Methyl5-(1-Methylethyl) ester
2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid O5-isopropyl ester O3-methyl ester
3,5-Pyridinedicarboxylic acid, 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-methyl 5-(1-methylethyl) ester (9CI)
2-Cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl 5-(1-Methylethyl) Ester, FR-34235, SKF-102362, Escor,
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 | [EINECS(EC#)]
805-887-5 | [Molecular Formula]
C19H19N3O6 | [MDL Number]
MFCD00867065 | [MOL File]
75530-68-6.mol | [Molecular Weight]
385.37 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Prisms | [Melting point ]
148-150°C | [Boiling point ]
511.83°C (rough estimate) | [density ]
1.3937 (rough estimate) | [refractive index ]
1.5900 (estimate) | [storage temp. ]
-20°C Freezer | [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 Information | Back Directory | [Chemical Properties]
Yellow Prisms | [Usage]
antihypertensive;calcium channel blocker | [Usage]
Used as an antihypertensive and antianginal | [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. | [Originator]
Fujisawa (Japan) | [Uses]
antihypertensive;calcium channel blocker | [Uses]
Used as an antihypertensive and antianginal | [Uses]
Used as an antihypertensive and antianginal. | [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 |
| Safety Data | Back Directory | [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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