3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase编号: 925
• 分子式: C18H20N2O6
• 平均质量: 360.3612
• 单一同位素质量: 360.13213637
• SMILES: O(C(=O)C1=C(NC(=C(C1c1cc([N+](=O)[O-])ccc1)C(=O)OC)C)C)CC
• Canonical SMILES: CCOC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC)C
• InChI: InChI=1S/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3
• InChIKey: PVHUJELLJLJGLN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC传统名: nitrendipine; 3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 商标名: Bayotensin; Baypress; Bylotensin; Deiten; Nidrel; Nitrepin
• 别名: 1,4-二氢-2,6-二甲基-4-(3-硝基苯)-3,5-吡啶二羧酸乙基甲酯; 尼群地平; Nitrendipin; Nitrendipino [INN-Spanish]; Nitrendipinum [INN-Latin]; Nitrendipine; 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Ethyl Methyl Ester; Bay e 5009; Bayotensin; Baypress; Bylotensin; Deiten; Nidrel; 3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; Nitrendipine

登记号

• CAS号: 39562-70-4
• EC号: 254-513-1
• MDL号: MFCD00082255
• PubChem SID: 160964388; 24277857; 46508817
• PubChem CID: 4507

理论计算性质

JChem

• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 1.9060917
• LogD (pH = 7.4): 2.1676996
• Log P: 2.1723022
• 摩尔折射率: 96.9133 cm^3
• 极化性: 35.811268 Å^3
• 极化表面积: 110.45 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.21
• LOG S: -4.41
• 溶解度: 1.42e-02 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble17.5 mg/mL; H2O: insoluble; Insoluble; Methanol; methanol: soluble15 mg/mL
• 外观: Pale Yellow Solid; yellow to green powder
• 熔点: 142-145°C
• 疏水性(logP): 2.4

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: US5653000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 20/21/22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H312-H332
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... ADORA3(140), CACNG1(786), KCNH1(3756), TTR(7276)rat ... Adora1(29290), Adora2a(25369)
• 生物活性机理: Calcium antagonist; Potassium channel (IK Ca ) blocker

产品相关信息

• 纯度: >95%
• 成盐信息: Free Base
• 应用领域: Antihypertensive agent; Induces NO-release in endothelial cells

详细说明

MP Biomedicals - 02159789

An L-type calcium channel blocker.

DrugBank - DB01054

• Drug Groups: approved
• Description: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive. [PubChem]
• Indication: For the treatment of mild to moderate hypertension
• Pharmacology: Nitrendipine, 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. Nitrendipine is similar to other peripheral vasodilators. Nitrendipine 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
• Protein Binding: > 99%
• External Links: Wikipedia

Selleck Chemicals - S2491

Research Area: Cardiovascular Disease
Biological Activity:
Nitrendipine is a dihydropyridine calcium channel blocker with an IC50 of 95 nM.It is an investigational dihydropyridine calcium-channel antagonist for the treatment of hypertension. Nitrendipine and BRL 38227 cause concentration-related inhibitions of the inositol phosphate response to histamine (100 µM). Similar maximal inhibitions were caused by each agent (55-58%). Inhibitory effect of BRL 38227 was reduced in potency (IC50 = 5.5 µM), but not magnitude, in the presence of glibenclamide (0.5 µM). [1][2]References on Nitrendipine[1] http://en.wikipedia.org/wiki/Nitrendipine, , [2] DICP., 1990 Feb, 24(2):167-75.

Sigma Aldrich - N144

Biochem/physiol Actions
Ca2+ channel blocker; anti-hypertensive.

Toronto Research Chemicals - N490150

Nitrendipine is a dihydropyridine calcium channel blocker. Nitrendipine is used in the treatment of primary (essential) hypertension to decrease blood pressure. Antihypertensive.

参考文献

• Santiago TM et al. DICP. 1990 Feb;24(2):167-75.
• Ventura, H.O., et al.: Am. J. Cardiol., 51, 783 (1983)
• Meyer, H. et al., Arzneim.-Forsch., 1981, 31, 407-409, (analogues, synth, pharmacol)
• Scriabine, A. et al., New Drugs Annu.: Cardiovasc. Drugs, 1984, 2, 37, (rev, pharmacol)
• Scriabine, A. et al., Nitrendipine 1984, (Eds.), Urban and Schwarzenberg, Baltimore, Md., 1984, (book)
• Kuhnert-Brandstaetter, M. et al., Sci. Pharm., 1986, 54, 71, (polymorphism)
• Hasegawa, G.R., Clin. Pharm., 1988, 7, 97, (rev)
• Soons, P.A. et al., Br. J. Clin. Pharmacol., 1991, 32, 11, (pharmacokinet, man)
• Soons, P.A. et al., Clin. Pharmacol. Ther. (St. Louis), 1991, 50, 394, (pharmacokinet, man)
• Mast, V. et al., Br. J. Clin. Pharmacol., 1992, 33, 51, (pharmacokinet, metab, enantiomers, man)
• Salameh, A. et al., Br. J. Pharmacol., 1996, 118, 1899, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 923
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EMR600