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N0165

Sigma-Aldrich

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
EC Number:
264-407-7
MDL number:
MFCD00478055
UNSPSC Code:
12352200
PubChem Substance ID:
329818405
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: >10 mg/mL

originator

Bayer

storage temp.

room temp

SMILES string

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

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

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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Xue-yan Chen et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 43(10), 1011-1018 (2009-01-09)
Effect of new calcium antagonist m-nisoldipine (m-Nis) on MCT-induced PH in rats and its mechanisms were investigated. Rats were injected with a single dose (60 mg x kg(-1)) of MCT subcutaneously to induce PH. Pulmonary haemodynamic measurement and lung tissue
Piero Ruggenenti et al.
Nature reviews. Nephrology, 6(6), 319-330 (2010-05-05)
Angiotensin II and other components of the renin-angiotensin-aldosterone system (RAAS) have a central role in the pathogenesis and progression of diabetic renal disease. A study in patients with type 1 diabetes and overt nephropathy found that RAAS inhibition with angiotensin-converting-enzyme
High-throughput screening of myometrial calcium-mobilization to identify modulators of uterine contractility
Herington J L, et al.
PLoS ONE, 10(11) (2015)
New Phenotypic Cytotoxicity Assay for ROS-inducing Compounds using Rat Renal Epithelial Cells
Uchiyama N, et al.
Toxicology Letters, 10(11) (2020)
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