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Nisoldipine

CAT: 0804-HY-17402-01Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-17402-01Size:100 mg
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Description
Nisoldipine (BAY-k 5552; Sular) is an orally active and blood-brain barrier-penetrating dihydropyridine calcium antagonist, with greater vascular selectivity than other calcium channel antagonists. Nisoldipine inhibits calcium influx and blocks voltage-gated calcium channels. Nisoldipine dilates coronary and systemic arteries. Nisoldipine has antihypertensive and anti-anginal activity. Nisoldipine also displays neuroprotective and antiviral activity[1][2][7][11].
CAS Number
63675-72-9
Product Name Alternative
BAY-k 5552
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Calcium Channel; Reactive Oxygen Species (ROS)
Type
Reference compound
Related Pathways
Immunology/Inflammation; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB
Applications
COVID-19-immunoregulation
Field of Research
Infection; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/Nisoldipine.html
Purity
99.56
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : < 0.1 mg/mL (ultrasonic)
Smiles
O=C(C1=C(C)NC(C)=C(C(OCC(C)C)=O)C1C2=CC=CC=C2[N+]([O-])=O)OC
Molecular Formula
C20H24N2O6
Molecular Weight
388.41
Precautions
H302, H315, H319, H335
References & Citations
[1]Hamilton SF, et al. 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.|[2]Sidhu G, et al. Nisoldipine. 2024 Feb 28. In: StatPearls [Internet]. Treasure Island (FL) : StatPearls Publishing; 2025 Jan–.|[3]Gökçe B, et al. Evaluation of in vitro effect, molecular docking, and molecular dynamics simulations of some dihydropyridine-class calcium channel blockers on human serum paraoxonase 1 (hPON1) enzyme activity. Biotechnol Appl Biochem. 2023 Oct;70 (5) :1707-1719. |[4]Missan S, et al. Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine. Br J Pharmacol. 2003 Nov;140 (5) :863-70.|[5]Sugawara H, et al. Antioxidant effects of calcium antagonists on rat myocardial membrane lipid peroxidation. Hypertens Res. 1996 Dec;19 (4) :223-8. |[6]Iimuro Y, et al. Nimodipine, a dihydropyridine-type calcium channel blocker, prevents alcoholic hepatitis caused by chronic intragastric ethanol exposure in the rat. Hepatology. 1996 Aug;24 (2) :391-7.|[7]Huang Y, et al. Nisoldipine Inhibits Influenza A Virus Infection by Interfering with Virus Internalization Process. Viruses. 2022 Dec 8;14 (12) :2738.|[8]Okada T, et al. Comparison of the effects of nifedipine and nisoldipine on coronary vasoconstriction in the Langendorff-perfused rat heart. J Cardiovasc Pharmacol. 2000 Jan;35 (1) :145-9.|[9] Godfraind T, et al. Effects of a chronic treatment by nisoldipine, a calcium antagonistic dihydropyridine, on arteries of spontaneously hypertensive rats. Circ Res. 1991 Mar;68 (3) :674-82. |[10]Campbell SE, et al. Cardiac structural remodelling after treatment of spontaneously hypertensive rats with nifedipine or nisoldipine. Cardiovasc Res. 1993 Jul;27 (7) :1350-8. |[11]Verma M, et al. Investigating the role of nisoldipine in foot-shock-induced post-traumatic stress disorder in mice. Fundam Clin Pharmacol. 2016 Apr;30 (2) :128-36.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
L-type calcium channel

Chemical Information

Nisoldipine

Methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate is a dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a methoxycarbonyl group at position 3, an o-nitrophenyl group at position 4, and an isobutoxycarbonyl group at position 5. The racemate, a calcium channel blocker, is used in the treatment of hypertension and angina pectoris. It is a member of dicarboxylic acids and O-substituted derivatives, a methyl ester, a C-nitro compound, a dihydropyridine and a diester.

CAS Number63675-72-9
PubChem CID4499
IUPAC Name3-O-methyl 5-O-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Molecular FormulaC20H24N2O6
Molecular Weight388.4
XLogP3.3
Topological Polar Surface Area110
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Heavy Atom Count28
Formal Charge0
Complexity704
SMILES
CC1=C(C(C(=C(N1)C)C(=O)OCC(C)C)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
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
Chemical Structure
2D Structure
2D structure of Nisoldipine
CAS: 63675-72-9
CID: 4499
Formula: C20H24N2O6
MW: 388.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight388.4
XLogP33.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass388.16343649
Monoisotopic Mass388.16343649
Topological Polar Surface Area110 Ų
Heavy Atom Count28
Formal Charge0
Complexity704
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

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