| Identification | Back Directory | [Name]
Manidipine | [CAS]
89226-50-6 | [Synonyms]
Manidipine
Franidipine
Manidipine 6300
Manidipine (Manyper)
89226-75-5 (Di-hydrochloride)
MANIDIPINE: MANIDIPINE DIHYDROCHLORIDE
1-diphenylmethyl-4-(2-hydroxyethyl)piperazine
3-(2-(4-Benzhydrylpiperazin-1-yl)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridi
2-(4-Diphenylmethyl-1-piperazinyl)ethyl methyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
2-(4-(Diphenylmethyl)-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
3-(2-(4-Benzhydrylpiperazin-1-yl)ethyl) 5-Methyl 2,6-diMethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
3-{2-[4-(diphenylMethyl)piperazin-1-yl]ethyl} 5-Methyl 2,6-diMethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 2-[4-(Diphenylmethyl)-1-piperazinyl]ethyl Methyl Ester
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-(4-(diphenylmethyl)-1-piperazinyl)ethyl methyl ester
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-[2-[4-(diphenylmethyl)piperazin-1-yl]ethyl]5-methyl ester
2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-[2-[4-(diphenylmethyl)-1-piperazinyl]ethyl]5-methyl ester
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-methyl 5-[2-[4-(diphenylmethyl)-1-piperazinyl]ethyl] ester
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 5-methyl 3-[2-[4-(diphenylmethyl)-1-piperazinyl]ethyl] ester
1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-[2-[4-(diphenylmethyl)-1-piperazinyl]ethyl] 5-methyl ester
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl methyl ester (9CI) | [EINECS(EC#)]
1806241-263-5 | [Molecular Formula]
C35H38N4O6 | [MDL Number]
MFCD00871291 | [MOL File]
89226-50-6.mol | [Molecular Weight]
610.7 |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Crystalline Solid | [Melting point ]
125-128°C | [Boiling point ]
722.0±60.0 °C(Predicted) | [density ]
1.232±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
Soluble in DMSO > 10 mM | [form ]
Powder | [pka]
6.12±0.10(Predicted) | [color ]
Light yellow to yellow | [LogP]
4.135 |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow Crystalline Solid | [Uses]
A dihydropyridine calcium channel blocker. Antihypertensive | [Uses]
Manidipine (Manyper) is a lipophilic, third-generation, highly vasoselective dihydropyridine calcium antagonist with an IC50 of 2.6 nM. It causes systemic vasodilation by inhibiting the voltage-dependent calcium inward currents in smooth muscle cells. It | [Description]
Manidipine is a dihydropyridine L- and T-type calcium channel blocker.1,2,3 It blocks recombinant rabbit L-type (α1Cα2/δβ1a) and human T-type (α1H) calcium channels expressed in Xenopus oocytes and native L-type channels in dissociated guinea pig cardiac ventricular cells (IC50 = 2.6 nM). Manidipine inhibits intracellular calcium increases induced by endothelin-1 (ET-1; Item No. 24127) in A7r5 rat vascular smooth muscle cells (ED50 = 1 nM) and potassium-induced contraction of isolated dog femoral and portal veins (IC50s = 24 and 2.1 nM, respectively).4,5 In vivo, it lowers blood pressure in spontaneously hypertensive rats (SHRs) when administered at a dose of 10 mg/kg and inhibits left ventricular hypertrophy in rats induced by isoproterenol (Item No. 15592) when administered at a dose of 3 mg/kg.6,7 Formulations containing manidipine have been used in the treatment of hypertension. | [Definition]
ChEBI: Manidipine is a diarylmethane. | [Synthesis]
Synthesis of 3-(2-(4-diphenylmethylpiperazin-1-yl)ethyl)-5-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate dihydrochloride as 3-(2-(4-diphenylmethylpiperazin-1-yl)ethyl)-5-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3 ,5-dicarboxylate in the following general steps:
1. 12 g of sodium hydroxide was weighed and 18 mL of water was added to prepare a 40% aqueous sodium hydroxide solution and cooled in an ice bath.
2. add manidipine hydrochloride (20.5 g) to a 500 mL three-necked flask pre-cooled in an ice bath with 100 mL of water.
3. With stirring on, slowly add the pre-prepared ice-cold 40% sodium hydroxide solution dropwise to the three-necked flask.
4. During the dropwise addition, 90mL of ethyl acetate was added.
5. After all bases are added, stop stirring and let stand for stratification.
6. After determining the pH of the aqueous phase to be 11-12, the liquid phase was separated.
7. The aqueous phase was extracted twice with ethyl acetate (30mL x 2) and the organic phases were combined.
8. The combined organic phases were washed once with water (50mL) and once with saturated sodium chloride solution (50mL).
9. The organic phase was dried with anhydrous sodium sulfate (15 g) for 2 hours.
10. After filtration, about 35 parts of the solvent were removed by evaporation under reduced pressure to give a yellow solid manidipine free base in 98% yield. | [References]
[1] Patent: CN105439942, 2016, A. Location in patent: Paragraph 0040; 0041; 0042 |
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