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Merck

N7634

Nifedipine

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C17H18N2O6
Número CAS:
Peso molecular:
346.33
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
244-598-3
MDL number:

Nombre del producto

Nifedipine, ≥98% (HPLC), powder

form

powder

color

yellow

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)

solubility

DMSO: soluble
ethanol: soluble

originator

Bayer

storage temp.

2-8°C

Quality Level

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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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

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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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the solubility of Product N7634, Nifidipine?

    Nifedipine can be dissolved in DMSO at 50 mg/ml1. It is sparingly soluble in absolute ethanol2. Herembert, T. et al., dissolved nifedipine in absolute ethanol (no concentration reported); the maximum ethanol concentration in cultures was 0.2% without any effect of solvent on the cells3. Nifedipine is soluble (g/L, at 20°C) in the following solvents: acetone, 250; methylene chloride, 160; chloroform, 140; ethyl acetate, 50; methanol, 26; ethanol, 17.4 It is practically insoluble in water. The solubilities at 37°C in buffer solutions of different pH values are: pH 4, 0.0058 g/L; pH 7, 0.0056 g/L; pH 9.0, 0.0078 g/L; pH 13, 0.006 g/L1. References:  1.  Ali, S.L., Analytical Profiles of Drug Substances, 18, 221, (1989).   2.  Martindale, The Extra Pharmacopoeia, 30th ed., 374, (1993).  and 3.  Herembert, T. et al. Brit. J. Pharmacol., 114, 1703, (1995).

  6. Are there any recommended dosages for Product N7634, Nifidipine, in vivo and in vitro?

    Nifedipine is reported to inhibit Ca2+-sensitive K+ channels at 100 μM1. Doses for different animals have been reported2,3. In randomly growing cultures of aortic cells of rats, nifedipine at 10 μM inhibited cell proliferation. References:  1.  Thomas-Young, R.J. et al. Biochim. Biophys. Acta, 1146, 81, (1993).      2.  Drug Dosages In Laboratory Animals: A Handbook, 3rd ed., Telford Press.  and 3.  Borchard, R.E. et al. Drug Dosage in Laboratory Animals, A Handbook, Third Edition, p. 315, The Telford Press, (1990).

  7. What is the half life of Product N7634, Nifidipine, in vivo?

    After administration by the mouth, the half-life is 2 to 5 hours 1. In plasma, about 92-98% binds to plasma proteins.  Nifedipine is completely metabolized. About 70% of a dose is excreted in the urine in 24 hours as metabolites including 5-methoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl) pyridine-3-carboxylic acid; dimethyl 2,6-dimethyl-4-(2-nitrophenyl pyridine-3,5-dicarboxylate and 2-hydroxymethyl-5-methoxycarbonyl-6-methyl-4-(2-nitrophenyl) pyridine-3-carboxylic acid and its lactone derivative. Up to 15% of a dose is eliminated in the feces as metabolites in 4 days 2. References:  1.  Martindale, 29th ed., pgs. 1509-1513.  2.  Clarke's Isolation and Identification of Drugs., 2nd ed., p. 811.

  8. Are there any recommended conditions that Product N7634, Nifidipine, should be used in?

    When exposed to daylight and certain wavelengths of artificial light, nifedipine readily converts to a nitrosophenylpyridine derivative. Exposure to ultra-violet light leads to the formation of a nitrophenylpyridine derivative. Therefore, USP recommends that assays be performed in the dark or under golden fluorescent or other low actinic light. Low actinic glassware should be used1.

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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 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)
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)
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)
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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