| Identification | Back Directory | [Name]
(+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate | [CAS]
104713-75-9 | [Synonyms]
BARNIDIPINE
Barnidipine-d5
Barnidipine(b)
YM-09730-5(Free base)
Barnidipine USP/EP/BP
(S)-3-((S)-1-Benzylpyrrolidin-3-yl)-5-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridin
(S)-3-((S)-1-Benzylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3
(+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
(S)-3-((S)-1-Benzylpyrrolidin-3-yl) 5-Methyl 2,6-diMethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
(4S)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 5-methyl 3-[(3S)-1-benzylpyrrolidin-3-yl] ester
(4S)-2,6-Dimethyl-1,4-dihydro-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 5-methyl 3-[(3S)-1-benzylpyrrolidin-3-yl] ester | [Molecular Formula]
C27H29N3O6 | [MDL Number]
MFCD23135231 | [MOL File]
104713-75-9.mol | [Molecular Weight]
491.54 |
| Chemical Properties | Back Directory | [Melting point ]
137-139° | [alpha ]
D20 +64.8° (c = 1 in methanol) | [Boiling point ]
614.5±55.0 °C(Predicted) | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Soluble in DMSO | [pka]
7.62±0.40(Predicted) |
| Hazard Information | Back Directory | [Description]
Barnidipine(104713-75-9) is a long-acting novel calcium antagonist that belongs to the dihydropyridine (DHP) group of calcium channel blockers. It contains two chiral centres thus can have four possible enantiomers. The active component is composed of a single optical isomer (3'S, 4S configuration), which is the most potent and longest-acting of the four enantiomers. Barnidipine has shown to be an effective antihypertensive agent in the management of hypertension in elderly patients and its efficacy is not negatively affected by age.
| [Originator]
Barnidipine,Yamanouchi | [Uses]
Barnidipine is used in the treatment of hypertension, barnidipine displays high affinity for the calcium channels of the smooth muscle cells in the vascular wall and selectivity against cardiovascular L-type calcium channels. | [Definition]
ChEBI:Barnidipine 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). | [Therapeutic Function]
Coronary vasodilator | [Side effects]
The side effects of barnidipine are typically mild to moderate and typically occur at the beginning of treatment. Common side effects include nausea, palpitations, flushed face, hot flashes, swelling, headache, heavy sensation in the head, dizziness, and a feeling of unsteadiness. Other reported side effects include redness, rash, itching, and sensitivity to sunlight. | [storage]
Store at -20°C | [Precautions]
The medicine may cause dizziness, etc. due to decreased blood pressure. Pay close attention when you work at heights, drive a car or operate dangerous machinery.
Since intake of grapefruit juice may enhance the effect of the medicine, refrain from drinking it. | [References]
[1] LIAUCHIAU-SUONG. Barnidipine: a new calcium channel blocker for hypertension treatment.[J]. Expert Review of Cardiovascular Therapy, 2005. DOI:10.1586/14779072.3.2.207.
[2] CHENGZHI-GANG. Synthesis and characterization of impurities of barnidipine hydrochloride, an antihypertensive drug substance.[J]. Molecules, 2014. DOI:10.3390/molecules19011344.
[3] https://www.ltl-pharma.com/common/pdf/product/hypoca/hypoca15_capsule_siori_en.pdf
[4] DEROSAGIUSEPPE. Barnidipine compared to lercanidipine in addition to losartan on endothelial damage and oxidative stress parameters in patients with hypertension and type 2 diabetes mellitus.[J]. BMC Cardiovascular Disorders, 2016. DOI:10.1186/s12872-016-0237-z. |
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