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N7634

Sigma-Aldrich

Nifedipine

≥98% (HPLC), powder, L-type Ca²⁺ channel blocker

Synonyme(s) :

1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester

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About This Item

Formule empirique (notation de Hill):
C17H18N2O6
Numéro CAS:
21829-25-4
Poids moléculaire :
346.33
Numéro CE :
244-598-3
Numéro MDL:
MFCD00057326
Code UNSPSC :
12352200
ID de substance PubChem :
24277855
Nomenclature NACRES :
NA.77

product name

Nifedipine, ≥98% (HPLC), powder

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder

Couleur

yellow

Solubilité

DMSO: soluble
ethanol: soluble

Auteur

Bayer

Température de stockage

2-8°C

Chaîne SMILES 

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

InChI

1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3

Clé InChI

HYIMSNHJOBLJNT-UHFFFAOYSA-N

Informations sur le gène

human ... ADORA2A(135) , ADORA3(140) , CACNA1C(775) , CACNA1D(776) , CACNA1F(778) , CACNA1S(779) , CACNA2D1(781) , CYP1A2(1544) , KCNH1(3756) , TTR(7276)
mouse ... Cacna1c(12288)
rat ... Adora1(29290) , Adora2a(25369) , Cacna1c(24239) , Cacna1d(29716) , Kcnj1(24521) , Kcnn4(65206) , Tbxas1(24886)

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Application

Nifedipine has been used:
  • to evaluate its effect on myenteric neuronal calcium current through R-type calcium channel in guinea pig small intestine
  • to evaluate the neuroprotective effect of L-type calcium channel blockers in cholinergic and dopaminergic neurons
  • to identify the effect of co-administration of nifedipine (anti-hypertensive drug) along with hypoglycemic drug on human umbilical vein cells (HUVECs)

Actions biochimiques/physiologiques

Nifedipine is a L-type Ca2+ channel blocker; and induces apoptosis in human glioblastoma cells. Nifedipine has neuroprotection activity and protects substantia nigra. Nifedipine has antioxidant potential. Nifedipine downregulates inflammatory cytokines like macrophage inflammatory protein-2 (MIP-2), tumor necrosis factor-α (TNF-α). Nifedipine has antihypertensive properties. Nifedipine inhibits extracellular region of adenosine A2a receptor (ADORA2A) gene.

Caractéristiques et avantages

This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Calcium Channels and Cyclic Nucleotide-Gated (CNG) and Hyperpolarization Activated Cyclic Nucleotide-Gated (HCN) Channels pages 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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

R-type calcium channels in myenteric neurons of guinea pig small intestine
Bian X, et al.
American Journal of Physiology: Gastrointestinal and Liver Physiology, 287(1), G134-G142 (2004)
Cell-type-specific interrogation of CeA Drd2 neurons to identify targets for pharmacological modulation of fear extinction
McCullough KM, et al.
Translational Psychiatry, 8(1), 164-164 (2018)
Combination therapy with cisplatin and nifedipine induces apoptosis in cisplatin-sensitive and cisplatin-resistant human glioblastoma cells
Kondo S, et al.
British Journal of Cancer, 71(2), 282-282 (1995)
Combination therapy of nifedipine and sulphonyl ureas exhibits a mutual antagonistic effect on the endothelial cell dysfunction induced by hyperglycemia linked to vascular disease
Wang LP, et al.
Cellular Physiology and Biochemistry, 38(6), 2337-2347 (2016)
Roberta Budriesi et al.
Journal of medicinal chemistry, 54(11), 3885-3894 (2011-05-17)
The pharmacology of the cystic fibrosis transmembrane conductance regulator (CFTR) Cl(-) channel has attracted significant interest in recent years with the aim to search for rational new therapies for diseases caused by CFTR malfunction. Mutations that abolish the function of
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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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