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Merck

N7634

Nifedipine

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H18N2O6
CAS Number:
21829-25-4
Molecular Weight:
346.33
NACRES:
NA.77
PubChem Substance ID:
24277855
UNSPSC Code:
12352200
EC Number:
244-598-3
MDL number:
MFCD00057326

Key Documents

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Product Name

Nifedipine, ≥98% (HPLC), powder

InChI key

HYIMSNHJOBLJNT-UHFFFAOYSA-N

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

SMILES string

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

assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: soluble, ethanol: soluble

originator

Bayer

storage temp.

2-8°C

Quality Level

200

Gene Information

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)

Biochem/physiol Actions

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.

Features and Benefits

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.

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP7182
MKCL4570
MKCG5574
MKCB9232
MKCB3044V

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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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고리형 뉴클레오타이드를 위한 생체 활성 저분자

고리형 AMP(cAMP), 고리형 GMP(cGMP), 고리형 ADP-리보스를 포함하여 고리형 뉴클레오타이드는 GPCR 활성화에 의해 개시된 세포내 이벤트의 2차 전달자로서 광범위하게 연구되었습니다. cAMP는 주로 cAMP 의존성 단백질 인산화효소(PKA)의 활성화를 통해 모든 진핵생물 세포에서 세포 기능을 변형시키지만 cAMP 개폐 이온 채널 및 cAMP에 의해 직접 활성화되는 구아닌 뉴클레오타이드 교환 인자를 통해서도 변형시킵니다.

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