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Merck
CN

N0165

Nisoldipine

≥98% (HPLC)

Synonym(s):

(±)-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, Sular

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About This Item

Empirical Formula (Hill Notation):
C20H24N2O6
CAS Number:
63675-72-9
Molecular Weight:
388.41
NACRES:
NA.77
PubChem Substance ID:
329818405
UNSPSC Code:
12352200
EC Number:
264-407-7
MDL number:
MFCD00478055

Key Documents

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Product Name

Nisoldipine, ≥98% (HPLC)

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

InChI key

VKQFCGNPDRICFG-UHFFFAOYSA-N

SMILES string

COC(=O)C1=C(C)NC(C)=C(C1c2ccccc2[N+]([O-])=O)C(=O)OCC(C)C

assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: >10 mg/mL

originator

Bayer

storage temp.

room temp

Quality Level

100

Gene Information

human ... CACNA1C(775), CACNA1D(776), CACNA1F(778), CACNA1S(779)

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Application

Nisoldipine has been used:
  • as a hit-antagonist to study its effects on oxytocin (OT)-induced myometrial Ca2+-mobilization and its potency to dampen uterine myometrial contractions
  • as a calcium channel blocker to study its effects on cell viability in a human hepatic cancer HepG2 and rat renal epithelial NRK52E cell line
  • as a component of the external IK1 recording solution to study the action potential in human pluripotent stem cell−derived cardiomyocytes (hiPS-CMs)

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.

Features and Benefits

This compound is featured on the Calcium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000503277
0000503279
0000503279
0000503277
0000226361

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Engineering of human cardiac muscle electromechanically matured to an adult-like phenotype
Ronaldson B K, et al.
Nature Protocols, 14(10), 2781-2817 (2019)
New Phenotypic Cytotoxicity Assay for ROS-inducing Compounds using Rat Renal Epithelial Cells
Uchiyama N, et al.
Toxicology Letters, 10(11) (2020)
High-throughput screening of myometrial calcium-mobilization to identify modulators of uterine contractility
Herington J L, et al.
PLoS ONE, 10(11) (2015)
Jennifer L Herington et al.
PloS one, 10(11), e0143243-e0143243 (2015-11-26)
The uterine myometrium (UT-myo) is a therapeutic target for preterm labor, labor induction, and postpartum hemorrhage. Stimulation of intracellular Ca2+-release in UT-myo cells by oxytocin is a final pathway controlling myometrial contractions. The goal of this study was to develop
Min Li et al.
Drug development and industrial pharmacy, 35(1), 65-72 (2008-09-30)
Rapid, sensitive, and selective high-performance liquid chromatography methods were developed and validated for determination of m-nisoldipine enantiomers in rat tissues. All of the samples were prepared based on a simple and efficient liquid-liquid extraction method. After validating that no racemation
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