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63675-72-9 分子结构
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3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

ChemBase编号:72796
分子式:C20H24N2O6
平均质量:388.41436
单一同位素质量:388.1634365
SMILES和InChIs

SMILES:
C1(=C(C(C(=C(N1)C)C(=O)OC)c1cccc(c1)[N+](=O)[O-])C(=O)OCC(C)C)C
Canonical SMILES:
COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OCC(C)C)C
InChI:
InChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-7-6-8-15(9-14)22(25)26/h6-9,11,18,21H,10H2,1-5H3
InChIKey:
MRSJBSHLMOBYSH-UHFFFAOYSA-N

引用这个纪录

CBID:72796 http://www.chembase.cn/molecule-72796.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
IUPAC传统名
3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
别名
Sular
Zadipina
Bay k 5552
Baymycard
Nisoldipine
CAS号
63675-72-9
PubChem SID
162037717
PubChem CID
10091655

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
Selleck Chemicals
S1748 external link 加入购物车 请登录
数据来源 数据ID
PubChem 10091655 external link

理论计算性质

理论计算性质

JChem
质子受体 质子供体
LogD (pH = 5.5) 2.7941644  LogD (pH = 7.4) 3.055208 
Log P 3.0597975  摩尔折射率 105.9089 cm3
极化性 39.47364 Å3 极化表面积 110.45 Å2
可自由旋转的化学键 里宾斯基五规则 true 

分子性质

分子性质

安全信息 产品相关信息 生物活性(PubChem)
保存条件
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成盐信息
Free Base expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals
Selleck Chemicals -  S1748 external link
Research Area
Description Cardiovascular Disease
Biological Activity
Description Nisoldipine (Sular) is a calcium channel blocker belonging to the dihydropyridines class, specific for L-type Cav1.2 with IC50 of 10 nM.
Targets L-type Cav1.2 channel
IC50 10 nM [1]
In Vitro Nisoldipine is a potent blocker of L-type calcium channels. Nisoldipine binds directly to inactive calcium channels stabilizing their inactive conformation Similar to other DHP CCBs. Nisoldipine displays selectivity for arterial smooth muscle cells due to great number of inactive channels and the alpha-1 subunit of the channel. [1] Nisoldipine is about 30 times less selective for delayed-rectifier K+ channels than for L-type Ca2+ channels, which inhibits IKr (rapidly activating delayed-rectifier K+ current) with IC50 of 23 μM, and IKs (slowly activating delayed-rectifier K+ current)with IC50 of 40 μM in guinea-pig ventricular myocytes. [2] Nisoldipine also displays antioxidant potency with IC50 of 28.2 μM both before and after the addition of active oxygen. This is tested by means of rat myocardial membrane lipid peroxidation with a nonenzymatic active oxygen-generating system (DHF/FeC13-ADP). [3]
In Vivo Nisoldipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through L-type calcium channels. This results in vasodilation and an overall decrease in blood pressure, based on which Nisoldipine is used to treat mild to moderate essential hypertension, chronic stable angina and Prinzmetal’s variant angina. [4] Nisoldipine shows some ability in patients with Timothy syndrome having Cav1.2 missense mutation G406R with IC50 of 267 nM, which is helpful to treat TS. [5]
Clinical Trials Phase I has been completed in a single-dose fasting bioequivalence study of Nisoldipine extended-release tablets in healthy volunteers.
Features Nisoldipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs.
Protocol
Kinase Assay [1]
Binding experiments of electrophysiology CHO cells expressing the subunit of the voltage-dependent L-type Ca2+ channel are cultrured in medium without serum in the presence of different concentrations of Nisoldipine. Then Ca2+ channel current elicited from a holding potential of -100 mV or -50 mV is recorded at room temperature with the whole-cell configuration of the patch-clamp method using the List EPC-7 patch-clamp amplifer and pClamp software. The concentration of competitor inhibiting 50% of the specific binding represents IC50.
Cell Assay [2]
Cell Lines Ventricular myocytes
Concentrations Dissolved in DMSO, final concentration 10-100 μM
Incubation Time 8-10 minutes
Methods The myocytes are bathed in normal Tyrode’s solution, held at -80 mV, and depolarised after 200-ms prepulses (-40mV) to more positive potentials for 500 ms at 0.1 Hz, tail currents are recorded on repolarisations to -40mV. The myocytes are exposed to 10-100 mM Nisoldipine for 8-10 minutes. Then the whole-cell membrane currents are recorded using an EPC-7 amplifier.
Animal Study [4]
Animal Models Male Wistar rats with chronic intragastric ethanol exposure
Formulation Dissolved in DMSO and diluted in saline
Doses 10 mg/kg
Administration Oral every day
References
[1] Morel N, et al. Br J Pharmacol, 1998, 125(5), 1005-1012.
[2] Missan S, et al. Br J Pharmacol, 2003, 140 (5), 863-870.
[3] Sugawara H, et al. Hypertens Res, 1996, 19 (4), 223-228.
[4] Iimuro Y, et al. Hepatology, 1996, 24(2), 391-397.
[5] Splawski I, et al. Cell, 2004, 119 (1), 19-31.

参考文献

参考文献

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