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Nitrendipine

CAT: 0804-HY-B0424-06Size: 1 gDry Ice: NoHazardous: No
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CAT#:0804-HY-B0424-06Size:1 g
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Description
Nitrendipine (BAY-E-5009) is an orally active analog of Nifedipine and dihydropyridine calcium channel blocker. Nitrendipine induces Apoptosis. Nitrendipine has antihypertensive effects. Nitrendipine blocks alcohol and Morphine withdrawal symptoms. Nitrendipine reduces right ventricular hypertrophy and pulmonary vascular changes induced by intermittent hypoxia. Nitrendipine has anticancer effects on neuroblastoma[1][2][3][4][5][6][7][8][9][10][11].
CAS Number
39562-70-4
Product Name Alternative
BAY-E-5009
UNSPSC
12352005
Hazard Statement
H312, H332, H362
Target
Apoptosis; Calcium Channel
Type
Reference compound
Related Pathways
Apoptosis; Membrane Transporter/Ion Channel; Neuronal Signaling
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/Nitrendipine.html
Purity
99.71
Solubility
DMSO : 50 mg/mL (ultrasonic) |H2O : < 0.1 mg/mL (ultrasonic)
Smiles
O=C(C1=C(C)NC(C)=C(C(OC)=O)C1C2=CC=CC([N+]([O-])=O)=C2)OCC
Molecular Formula
C18H20N2O6
Molecular Weight
360.36
Precautions
H312, H332, H362
References & Citations
[1]Bellemann, P., et al., [3H]-Nitrendipine, a potent calcium antagonist, binds with high affinity to cardiac membranes. Arzneimittelforschung, 1981. 31 (12) : p. 2064-7.|[2]S Kazda, et al. Diuretic effect of nitrendipine contributes to its antihypertensive efficacy: a review. J Cardiovasc Pharmacol. 1988;12 Suppl 4:S1-5.|[3]He-Hui Xie, et al. Synergism of atenolol and nitrendipine on hemodynamic amelioration and organ protection in hypertensive rats. J Hypertens. 2005 Jan;23 (1) :193-201.|[4]Rivera I, et al. Nitrendipine, an antihypertensive alpha calcium channel blocker, is cytotoxic to neuroblastoma cells. Molecular & Cellular Toxicology, 2019, 15: 469-475.|[5]Watson WP, et al. The differential effects of felodipine and nitrendipine on cerebral dihydropyridine binding ex vivo and the ethanol withdrawal syndrome in mice. Br J Pharmacol. 1994 Aug;112 (4) :1017-24.|[6]RABANI, et al. Acute and chronic effects of nitrendipine on naloxone precipitated morphine withdrawal in mice. 2004, 109-114.|[7]Gatch MB. Nitrendipine blocks the nociceptive effects of chronically administered ethanol. Alcohol Clin Exp Res. 2002 Aug;26 (8) :1181-7.|[8]Aktay G, et al. Protective Effect of Nitrendipine on Naphthalene-Induced Oxidative Stress. Eczacilik Fakultesi Dergisi-Gazi Universitesi, 2000, 17 (1) : 19-24. |[9]Michael JR, et al. Nitrendipine attenuates the pulmonary vascular remodeling and right ventricular hypertrophy caused by intermittent hypoxia in rats. Am Rev Respir Dis. 1986 Mar;133 (3) :375-9. |[10]Han P, et al. Synergism of hydrochlorothiazide and nitrendipine on reduction of blood pressure and blood pressure variability in spontaneously hypertensive rats. Acta Pharmacol Sin. 2006 Dec;27 (12) :1575-9. |[11]M Bursztyn, et al. Nitrendipine improves glucose tolerance and deoxyglucose uptake in hypertensive rats. Hypertension. 1994 Jun;23 (6 Pt 2) :1051-3.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Nitrendipine

Nitrendipine is a dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension. It has a role as a geroprotector, a vasodilator agent, an antihypertensive agent and a calcium channel blocker. It is a member of dicarboxylic acids and O-substituted derivatives, an ethyl ester, a methyl ester, a C-nitro compound, a dihydropyridine and a diester.

CAS Number39562-70-4
PubChem CID4507
IUPAC Name5-O-ethyl 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Molecular FormulaC18H20N2O6
Molecular Weight360.4
XLogP2.9
Topological Polar Surface Area110
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Heavy Atom Count26
Formal Charge0
Complexity661
SMILES
CCOC(=O)C1=C(NC(=C(C1C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OC)C)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
Chemical Structure
2D Structure
2D structure of Nitrendipine
CAS: 39562-70-4
CID: 4507
Formula: C18H20N2O6
MW: 360.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight360.4
XLogP32.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Exact Mass360.13213636
Monoisotopic Mass360.13213636
Topological Polar Surface Area110 Ų
Heavy Atom Count26
Formal Charge0
Complexity661
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
B1393-SNitrendipine
sc-478335(+) -Nitrendipine
TRC-N490145-25MG(+)-Nitrendipine
TRC-N490155-25MG(-)-Nitrendipine

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