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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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1 G
$155.00
5 G
$448.00
10 G
$798.00
25 G
$1,060.00
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1 G
$155.00
5 G
$448.00
10 G
$798.00
25 G
$1,060.00
About This Item
Empirical Formula (Hill Notation):
C17H18N2O6
CAS Number:
Molecular Weight:
346.33
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
product name
Nifedipine, ≥98% (HPLC), powder
Quality Level
Assay
≥98% (HPLC)
form
powder
color
yellow
solubility
DMSO: soluble
ethanol: soluble
originator
Bayer
storage temp.
2-8°C
SMILES string
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
InChI key
HYIMSNHJOBLJNT-UHFFFAOYSA-N
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[1]
- to evaluate the neuroprotective effect of L-type calcium channel blockers in cholinergic and dopaminergic neurons[2]
- to identify the effect of co-administration of nifedipine (anti-hypertensive drug) along with hypoglycemic drug on human umbilical vein cells (HUVECs)[3]
Biochem/physiol Actions
Nifedipine is a L-type Ca2+ channel blocker;[1] and induces apoptosis in human glioblastoma cells.[4] 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).[2] Nifedipine has antihypertensive properties.[3] Nifedipine inhibits extracellular region of adenosine A2a receptor (ADORA2A) gene.[5]
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 1
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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Customers Also Viewed
Combination therapy of nifedipine and sulphonyl ureas exhibits a mutual antagonistic effect on the endothelial cell dysfunction induced by hyperglycemia linked to vascular disease
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Cellular Physiology and Biochemistry, 38(6), 2337-2347 (2016)
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)
Cell-type-specific interrogation of CeA Drd2 neurons to identify targets for pharmacological modulation of fear extinction
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Translational Psychiatry, 8(1), 164-164 (2018)
R-type calcium channels in myenteric neurons of guinea pig small intestine
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American Journal of Physiology: Gastrointestinal and Liver Physiology, 287(1), G134-G142 (2004)
An Liu et al.
Neurochemical research, 44(3), 683-691 (2017-10-21)
Abnormal processing of amyloid precursor protein (APP) and aggregation of the Aβ peptide are known to play a key role in the pathogenesis of Alzheimer disease, but the function of endogenous APP under normal physiological conditions remains poorly understood. In
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What is the Department of Transportation shipping information for this product?
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Are there any recommended dosages for Product N7634, Nifidipine, in vivo and in vitro?
1 answer-
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).
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Are there any recommended conditions that Product N7634, Nifidipine, should be used in?
1 answer-
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.
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What is the half life of Product N7634, Nifidipine, in vivo?
1 answer-
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.
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What is the solubility of Product N7634, Nifidipine?
1 answer-
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).
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