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

• ChemBase ID: 925
• Molecular Formular: C18H20N2O6
• Molecular Mass: 360.3612
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: nitrendipine; 3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• Brand Name: Bayotensin; Baypress; Bylotensin; Deiten; Nidrel; Nitrepin
• Synonyms: 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; 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.9060917
• LogD (pH = 7.4): 2.1676996
• Log P: 2.1723022
• Molar Refractivity: 96.9133 cm^3
• Polarizability: 35.811268 Å^3
• Polar Surface Area: 110.45 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.21
• LOG S: -4.41
• Solubility (Water): 1.42e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble17.5 mg/mL; H2O: insoluble; Insoluble; Methanol; methanol: soluble15 mg/mL
• Apperance: Pale Yellow Solid; yellow to green powder
• Melting Point: 142-145°C
• Hydrophobicity(logP): 2.4

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: US5653000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADORA3(140), CACNG1(786), KCNH1(3756), TTR(7276)rat ... Adora1(29290), Adora2a(25369)
• Mechanism of Action: Calcium antagonist; Potassium channel (IK Ca ) blocker

Product Information

• Purity: >95%
• Salt Data: Free Base
• Application(s): Antihypertensive agent; Induces NO-release in endothelial cells

DETAILS

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.

REFERENCES

• 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)
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• 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