| Identification | More | [Name]
Barnidipine | [CAS]
104757-53-1 | [Synonyms]
(+)-(3's,4s)-1-benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
BARNIDIPINE HCL
BARNIDIPINE HYDROCHLORIDE
hydrochloride,(s-(r*,r*))-hyl1-(phenylmethyl)-3-pyrrolidinyleste
ly198561
mepirodipinehydrochloride
ym09730-5
ym730
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl (3S)-1-(phenylmethyl)-3-pyrrolidinyl ester, (4S)-
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 1-(phenylmethyl)-3-pyrrolidinyl ester, [S-(R*,R*)]-
Hypoca
Mepirodipine
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl (3S)-1-(phenylmethyl)-3-pyrrolidinyl ester, monohydrochloride, (4S)- | [Molecular Formula]
C27H30ClN3O6 | [MDL Number]
MFCD00915772 | [Molecular Weight]
528 | [MOL File]
104757-53-1.mol |
| Hazard Information | Back Directory | [Description]
Barnidipine hydrochloride(104757-53-1), chemically known as (3S)-1-benzyl-3-pyrrolidinylmethyl-(4S)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride, is a new long-acting dihydropyridine calcium antagonist developed and marketed by Yamanouchi Pharmaceutical (now Astellas Pharma). This medication effectively lowers blood pressure without impacting heart rate by specifically targeting calcium channels responsible for transmembrane potential. By inhibiting calcium influx into cells, it selectively relaxes smooth muscle in peripheral and coronary blood vessels.
| [Chemical Properties]
Pale Yellow Solid. Melting point 226-228°C. [α]D20+116.4° (C=1, methanol). Insoluble in water. Acute toxicity LD50 male and female rats (mg/kg): 105, 113 Oral. | [Originator]
Yamanouchi (Japan) | [Uses]
Barnidipine hydrochloride is a vasodilating dihydropyridine calcium antagonist useful in the treatment of primary hypertension and renal hypertension. In experimental animals, its hypotensive effect was more potent and longer acting than nicardipine, nifedipine and nitrendipine. | [Definition]
ChEBI: Barnidipine hydrochloride is a dihydropyridine. 1,4-Dihydropyridine calcium antagonist with antihypertensive and diuretic effects. It is a potential candidate in the treatment of patients with renal parenchymal hypertension. | [Manufacturing Process]
In 5 ml of isopropyl alcohol were dissolved 1.5 g (0.01 mole) of 3-
nitrobenzaldehyde, 2.6 g (0.01 mole) of 1-benzyl-3-acetoacetyloxypyrrolidine,
and 1.3 g (0.01 mole) of β-aminocrotonic acid methyl ester and then the
solution was refluxed for 8 hours. The solvent was distilled off under reduced
pressure, the residue obtained was dissolved in a small amount of chloroform,
and the solution was applied to silica gel column chromatography (column
diameter 1.5 cm, height 20 cm, and about 200 ml of chloroform was used as
the eluent). The eluates were collected and concentrated to give 3.4 g of oily 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-
(1-benzylpyrrolidin-3-yl)ester-5-methyl ester: [α]D
20=+64.8° (c = 1 in
methanol). | [Brand name]
Hypoca | [Therapeutic Function]
Coronary vasodilator | [Biological Activity]
Barnidipine is a dihydropyridine calcium channel blocker that has an IC50 value of 0.35 nM in potassium-induced tonic contraction of pig coronary artery. It demonstrates antihypertensive activity by reducing peripheral vascular resistance. It decreases blood pressure in spontaneously hypertensive rats when administered orally at 1 and 3 mg/kg per day. Formulations containing barnidipine have been used as a treatment for hypertension. | [in vitro]
the effects of barnidipine on l-type ca(2+) current (i(ca(l))) were investigated in rat ventricular cardiomyocytes. it was found that barnidipine reduced i(ca(l)) in a concentration and voltage dependent manne. barnidipine induced a leftward shift of the steady-state inactivation curve of i(ca(l)) [1]. | [in vivo]
a previous study was conducted to investigate the influence of barnidipine treatment on early stage hypertension by determining the mesenteric and renal arteries as well as the kidney in l-name-induced hypertensive rats. barnidipine was applied to rats after 2 weeks of l-name administration, and continued for the next 3 weeks concomitantly with l-name. histopathological studies verified structural alterations in the arteries and the kidney. moreover, a decrease in endothelial nitric oxide synthase expression was observed both in the arteries and kidney of hypertensive rats with barnidipine treatment [2]. | [storage]
4°C, away from moisture and light | [References]
[1] wegener jw, meyrer h, rupp j, nawrath h. barnidipine block of l-type ca(2+) channel currents in rat ventricular cardiomyocytes. br j pharmacol. 2000 aug;130(8):2015-23.
[2] alp yildirim fi, eker kizilay d, ergin b, balci ekmeki, topal g, kucur m, demirci tansel c, uyde doan bs. barnidipine ameliorates the vascular and renal injury in l-name-induced hypertensive rats. eur j pharmacol. 2015 oct 5;764:433-42.
[3] derosa g, mugellini a, pesce rm, d'angelo a, maffioli p. barnidipine compared to lercanidipine in addition to losartan on endothelial damage and oxidative stress parameters in patients with hypertension and type 2 diabetes mellitus. bmc cardiovasc disord. 2016 apr 12;16:66. |
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