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Barnidipine hydrochloride

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Barnidipine hydrochloride Basic information

Product Name:
Barnidipine hydrochloride
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
Product Categories:
  • Aromatics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • API
  • Heterocycle-Pyridine series
Mol File:
104757-53-1.mol
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Barnidipine hydrochloride 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
color 
Light yellow to yellow
CAS DataBase Reference
104757-53-1(CAS DataBase Reference)
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Safety Information

Toxicity
LD50 orally in male, female rats: 105, 113 mg/kg (Satoh)
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Barnidipine hydrochloride Usage And Synthesis

Description

Barnidipine hydrochloride, 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].

References

[1] WEGENERJ W. Barnidipine block of L-type Ca(2+) channel currents in rat ventricular cardiomyocytes.[J]. British Journal of Pharmacology, 2000. DOI:10.1038/sj.bjp.0703514.
[2] ALP YILDIRIMF ILKAY. Barnidipine ameliorates the vascular and renal injury in L-NAME-induced hypertensive rats.[J]. European journal of pharmacology, 2015. DOI:10.1016/j.ejphar.2015.07.033.
[3] CHENGZHI-GANG. Synthesis and characterization of impurities of barnidipine hydrochloride, an antihypertensive drug substance.[J]. Molecules, 2014. DOI:10.3390/molecules19011344.

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