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

ChemBase编号:284
分子式:C20H24N2O6
平均质量:388.41436
单一同位素质量:388.1634365
SMILES和InChIs

SMILES:
O(C(=O)C1=C(NC(=C(C1c1c([N+](=O)[O-])cccc1)C(=O)OC)C)C)CC(C)C
Canonical SMILES:
COC(=O)C1=C(C)NC(=C(C1c1ccccc1[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)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3
InChIKey:
VKQFCGNPDRICFG-UHFFFAOYSA-N

引用这个纪录

CBID:284 http://www.chembase.cn/molecule-284.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-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
IUPAC传统名
nisoldipine (product)
3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
nisoldipino
商标名
Baymycard
Nisocor
Sular
Syscor
Zadipina
别名
Nisoldipinum [INN-Latin]
Nisoldipino [INN-Spanish]
Nisoldipin
Nisoldipine
3-isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
(±)-Isobutyl methyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate
1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester
Bay k 5552
Baymycard, Norvasc, Syscor, Zadipina, 1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl 2-Methylpropyl Ester
Sular
Nisoldipine
Nisocor
3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
CAS号
63675-72-9
EC号
264-407-7
MDL号
MFCD00478055
PubChem SID
160963747
46504546
PubChem CID
4499

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 2.8399477  LogD (pH = 7.4) 3.056208 
Log P 3.0597975  摩尔折射率 105.9089 cm3
极化性 39.47395 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 
Log P 3.63  LOG S -4.83 
溶解度 5.77e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Chloroform expand 查看数据来源
DMSO: >10 mg/mL expand 查看数据来源
Ethanol expand 查看数据来源
Methanol expand 查看数据来源
外观
yellow powder expand 查看数据来源
Yellow Solid expand 查看数据来源
熔点
147-148°C expand 查看数据来源
疏水性(logP)
3.1 expand 查看数据来源
4.582 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
RTECS编号
US7975600 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
20/21/22 expand 查看数据来源
安全公开号
36 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302-H312 expand 查看数据来源
GHS警示性声明
P280 expand 查看数据来源
保存温度
room temp expand 查看数据来源
生物活性机理
By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum expand 查看数据来源
Calcium channel antagonist expand 查看数据来源
causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, expand 查看数据来源
decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload expand 查看数据来源
inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes. expand 查看数据来源
The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
95% expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Antihypertensive agent expand 查看数据来源
Coronary vasodilator expand 查看数据来源
Empirical Formula (Hill Notation)
C20H24N2O6 expand 查看数据来源

详细说明

详细说明

Sigma Aldrich Sigma Aldrich TRC TRC DrugBank DrugBank
Sigma Aldrich -  N0165 external link
Biochem/physiol Actions
L-type (CaV1.2) calcium channel blocker; dihydropyridine-type calcium channel blocker with selectivity for smooth muscle (CaV1.2b) over cardiac muscle (CaV1.2a). Arterial vasodilator and antihypertensive agent.
Toronto Research Chemicals -  N489125 external link
Dihydropyridine calcium channel blocker. Antihypertensive and antianginal.
DrugBank -  DB00401 external link
Item Information
Drug Groups approved
Description Nisoldipine is a 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, nisoldipine prevents calcium-dependent smooth muscle contraction and subsequent vasoconstriction. Nisoldipine may be used in alone or in combination with other agents in the management of hypertension.
Indication For the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents.
Pharmacology Nisoldipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Nisoldipine is similar to other peripheral vasodilators. Nisoldipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
Affected Organisms
Humans and other mammals
Biotransformation Pre-systemic metabolism in the gut wall, and this metabolism decreases from the proximal to the distal parts of the intestine. Nisoldipine is highly metabolized; 5 major urinary metabolites have been identified. The major biotransformation pathway appears to be the hydroxylation of the isobutyl ester. A hydroxylated derivative of the side chain, present in plasma at concentrations approximately equal to the parent compound, appears to be the only active metabolite and has about 10% of the activity of the parent compound. Cytochrome P450 enzymes are believed to play a major role in the metabolism of nisoldipine. The particular isoenzyme system responsible for its metabolism has not been identified, but other dihydropyridines are metabolized by cytochrome P450 IIIA4.
Absorption Relatively well absorbed into the systemic circulation with 87% of the radiolabeled drug recovered in urine and feces. The absolute bioavailability of nisoldipine is about 5%.
Half Life 7-12 hours
Protein Binding 99%
Elimination Although 60-80% of an oral dose undergoes urinary excretion, only traces of unchanged nisoldipine are found in urine.
References
Mielcarek J, Grobelny P, Szamburska O: The effect of beta-carotene on the photostability of nisoldipine. Methods Find Exp Clin Pharmacol. 2005 Apr;27(3):167-71. [Pubmed]
Missan S, Zhabyeyev P, Dyachok O, Jones SE, McDonald TF: Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine. Br J Pharmacol. 2003 Nov;140(5):863-70. Epub 2003 Oct 6. [Pubmed]
Hamilton SF, Houle LM, Thadani U: Rapid-release and coat-core formulations of nisoldipine in treatment of hypertension, angina, and heart failure. Heart Dis. 1999 Nov-Dec;1(5):279-88. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Mielcarek J, Grobelny P, Szamburska O: The effect of beta-carotene on the photostability of nisoldipine. Methods Find Exp Clin Pharmacol. 2005 Apr;27(3):167-71. Pubmed
  • Missan S, Zhabyeyev P, Dyachok O, Jones SE, McDonald TF: Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine. Br J Pharmacol. 2003 Nov;140(5):863-70. Epub 2003 Oct 6. Pubmed
  • Hamilton SF, Houle LM, Thadani U: Rapid-release and coat-core formulations of nisoldipine in treatment of hypertension, angina, and heart failure. Heart Dis. 1999 Nov-Dec;1(5):279-88. Pubmed
  • Kazda, S., et al.: Arzneimittel-Forsch., 30, 2144 (1980)
  • Pasanisi, F., et al.: Eur. J. Clin. Pharmacol., 29, 21 (1980)
  • Lam, J., et al.: J. Am. Col. Cardiol., 6, 447 (1985)
  • Ger. Pat., 1977, 2 549 568; CA, 87, 84831d, (synth, pharmacol)
  • Kazda, S. et al., Arzneim.-Forsch., 1980, 30, 2144, (pharmacol)
  • Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 13022
  • Kazda, S. et al., New Drugs Annu.: Cardiovasc. Drugs, 1983, 1, 243, (rev)
  • Hugenholtz, P.G. et al., Nisoldipine 1987, Springer-Verlag, Berlin, 1987, (book)
  • Ahr, H.J. et al., Arzneim.-Forsch., 1988, 38, 1093; 1099; 1105, (pharmacokinet)
  • Friedel, H.A. et al., Drugs, 1988, 36, 682, (rev)
  • Fossheim, R. et al., J. Med. Chem., 1988, 31, 300, (cryst struct)
  • Mitchell, J. et al., J. Clin. Pharmacol., 1993, 33, 46, (rev)
  • Langtry, H.D. et al., Drugs, 1997, 54, 867-884, (rev)
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专利

专利

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