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N0750010

Nifedipine impurity A

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Oxidized Nifedipine, 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:
41116107
PubChem Substance ID:
329818456
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

nifedipine

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

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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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Nifedipine impurity A EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

CYP3A4 nifedipine metabolite. Nifedipine (parent compound) is an antianginal and antihypertensive agent.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

related product

Product No.
Description
Pricing

1463508

Nifedipine, United States Pharmacopeia (USP) Reference Standard

N0750000

Nifedipine, European Pharmacopoeia (EP) Reference Standard

1463600

Nifedipine Nitrophenylpyridine Analog, United States Pharmacopeia (USP) Reference Standard

N0750015

Nifedipine impurity B, European Pharmacopoeia (EP) Reference Standard

1463701

Nifedipine Nitrosophenylpyridine Analog, United States Pharmacopeia (USP) Reference Standard

PHR1290

Nifedipine, Pharmaceutical Secondary Standard; Certified Reference Material

BP462

Nifedipine, British Pharmacopoeia (BP) Reference Standard

BP866

Dimethyl 2,6-dimethyl-4-(2-nitrosophenyl)-3,5-pyridinedicarboxylate, British Pharmacopoeia (BP) Reference Standard

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338 + P310

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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
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
Occurrence and measurement of nifedipine and its nitropyridine derivatives in human blood plasma.
J Dokladalova et al.
Journal of chromatography, 231(2), 451-458 (1982-09-10)
Tsai-Shin Chiang et al.
PloS one, 9(4), e94885-e94885 (2014-04-16)
Human hepatoma cell lines are commonly used as alternatives to primary hepatocytes for the study of drug metabolism in vitro. However, the phase I cytochrome P450 (CYP) enzyme activities in these cell lines occur at a much lower level than
Camille C Savary et al.
Drug metabolism and disposition: the biological fate of chemicals, 42(8), 1235-1240 (2014-05-17)
Humans are usually exposed to several pesticides simultaneously; consequently, combined actions between pesticides themselves or between pesticides and other chemicals need to be addressed in the risk assessment. Many pesticides are efficient activators of pregnane X receptor (PXR) and/or constitutive
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