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UC167

Sigma-Aldrich

Oxidized Nifedipine

powder, ~95% (HPLC)

Synonym(s):

2,6-Dimethyl-4-(2´-nitrophenyl)-3,5-pyridinecarboxylic acid dimethyl ester

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About This Item

Empirical Formula (Hill Notation):
C17H16N2O6
CAS Number:
67035-22-7
Molecular Weight:
344.32
MDL number:
MFCD00153847
UNSPSC Code:
12161501
PubChem Substance ID:
329827652
NACRES:
NA.77

Assay

~95% (HPLC)

form

powder

color

yellow

mp

100-105 °C

storage temp.

2-8°C

SMILES string

COC(=O)c1c(C)nc(C)c(C(=O)OC)c1-c2ccccc2[N+]([O-])=O

InChI

1S/C17H16N2O6/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/h5-8H,1-4H3

InChI key

UMQHJQGNGLQJPF-UHFFFAOYSA-N

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Application

Oxidized Nifedipine may be used:
  • to study enzyme kinetics using UV high-performance liquid chromatography (UV-HPLC)
  • as a standard in calibration curve preparation in high-performance liquid chromatography (HPLC) for the quantification of cytochrome P450 3A4 (CYP3A4)-mediated nifedipine oxidation in human microsomes
  • in nifedipine metabolism activity assay of Hep G2 cells transfected with hepatocyte nuclear factor-1α(HNF1α)

Oxidized nifedipine has been used for apoptotic signaling studies in dopaminergic neurons.

Biochem/physiol Actions

Nifedipine is a dihydropyridine derivative and a calcium channel blocker. It is used in treating hypertension and angina pectoris. Oxidized Nifedipine is an oxidation product of nifedipine generated either by exposure to UV or day light. The enzyme cytochrome P450 3A (CYP3A4) metabolizes nifedipine.
CYP3A4 nifedipine metabolite. Nifedipine (parent compound) is an antianginal and antihypertensive agent.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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CYP3As catalyze nifedipine oxidation in pig liver microsomes: Enzyme kinetics, inhibition and functional expression
Jiang J, et al.
Catalysis Communications, 12(8), 694-697 (2011)
Gabriel A de Erausquin et al.
Molecular pharmacology, 63(4), 784-790 (2003-03-20)
We describe a new molecular mechanism of cell death by excitotoxicity mediated through nuclear transcription factor kappa B (NF kappa B) in rat embryonic cultures of dopaminergic neurons. Treatment of mesencephalic cultures with alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) resulted in a number
Wiriyaporn Sumsakul et al.
Asian Pacific journal of tropical medicine, 8(11), 914-918 (2015-11-29)
To investigate the propensity of plumbagin to inhibit the three isoforms of human cytochrome P450 (CYP), i.e., CYP1A2, CYP2C19, and CYP3A4 using human liver microsomes in vitro. Inhibitory effects of plumbagin on the three human CYP isoforms were investigated using pooled
D G Waller et al.
British journal of clinical pharmacology, 18(6), 951-954 (1984-12-01)
Oral administration of nifedipine (20 and 30 mg tablets) to six volunteers was associated with a bioavailability of 0.43 and the presence of its nitropyridine analogue in the plasma. This metabolite was present in only trace amounts in samples taken
J L Born et al.
Chemical research in toxicology, 2(1), 57-59 (1989-01-01)
The primary deuterium isotope effect on Vm for the microsomal oxidation of the dihydropyridine calcium entry blocker nifedipine [4-(2-nitrophenyl)-2,6-dimethyl-3,5- bis(methoxycarbonyl)-1,4-dihydropyridine] has been measured. The magnitude of the kinetic isotope effect, 6.7, suggests that the rate-limiting step in the mechanism of
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