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| Barnidipine Basic information |
Product Name: | Barnidipine | Synonyms: | hydrochloride,(s-(r*,r*))-hyl1-(phenylmethyl)-3-pyrrolidinyleste;ly198561;BARNIDIPINE HCL;BARNIDIPINE HYDROCHLORIDE;(+)-(3's,4s)-1-benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate;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 | CAS: | 104757-53-1 | MF: | C27H30ClN3O6 | MW: | 528 | EINECS: | | Product Categories: | Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;Heterocycle-Pyridine series | Mol File: | 104757-53-1.mol | |
| Barnidipine Chemical Properties |
Melting point | 223-226°C | alpha | D20 +116.4° (c = 1 in methanol) | storage temp. | Sealed in dry,Room Temperature | solubility | insoluble in H2O; insoluble in EtOH; ≥16.3 mg/mL in DMSO with gentle warming | form | A crystalline solid | CAS DataBase Reference | 104757-53-1(CAS DataBase Reference) |
Toxicity | LD50 orally in male, female rats: 105, 113 mg/kg (Satoh) |
| Barnidipine Usage And Synthesis |
Description | 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. | Description | Barnidipine hydrochloride is a vasodilating dihydropyridine calcium antagonist useful
in the treatment of hypertension. In experimental animals, its hypotensive effect was
more potent and longer acting than nicardipine, nifedipine and nitrendipine. | Chemical Properties | Pale Yellow Solid | Originator | Yamanouchi (Japan) | Uses | 1,4-Dihydropyridine calcium antagonist with antihypertensive and diuretic effects. A potential candidate in the treatment of patients with renal parenchymal hypertension. | Definition | ChEBI: Barnidipine hydrochloride is a dihydropyridine. | 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 | 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]. | 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. |
| Barnidipine Preparation Products And Raw materials |
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