ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Methylpyridine OXIDIZED NIFEDIPINE

OXIDIZED NIFEDIPINE

Product NameOXIDIZED NIFEDIPINE
CAS67035-22-7
MFC17H16N2O6
MW344.32
EINECS
MOL File67035-22-7.mol

Chemical Properties

Melting point	100-105 °C
Boiling point	443.7±45.0 °C(Predicted)
Density	1.284±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	powder
pka	1.55±0.29(Predicted)
color	yellow
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
InChIKey	UMQHJQGNGLQJPF-UHFFFAOYSA-N
SMILES	COC(=O)c1c(C)nc(C)c(C(=O)OC)c1-c2ccccc2[N+]([O-])=O
EPA Substance Registry System	3,5-Pyridinedicarboxylic acid, 2,6-dimethyl-4-(2-nitrophenyl)-,3,5-dimethyl ester (67035-22-7)

Safety Information

Hazard Codes	Xi
Risk Statements	41
Safety Statements	26-39
WGK Germany	2
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Dam. 1

Usage And Synthesis

Description

Dehydro nifedipine is an active metabolite of nifedipine , a calcium channel blocker present in formulations used to treat hypertension and angina. Dehydro nifedipine is formed when nifedipine is metabolized by the cytochrome P450 (CYP) isomers CYP3A4 and CYP3A5. Dehydro nifedipine inhibits glucose uptake in PC-12 cells with an IC₅₀ value of 130 μM.

Chemical Properties

Pale Yellow Solid

Uses

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

Uses

The main Nifedipine metabolite in human plasma

Definition

ChEBI: Dehydronifedipine is a phenylpyridine.

Biochem/physiol Actions

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

References

[1] T. D. ARDIZZONE D D Xiao Hong Lu. Calcium-independent inhibition of glucose transport in PC-12 and L6 cells by calcium channel antagonists.[J]. American journal of physiology. Cell physiology, 2002, 27 1: C579-86. DOI: 10.1152/ajpcell.00451.2001
[2] KIRAN C PATKI D J G Lisa L Von Moltke. In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5.[J]. Drug Metabolism and Disposition, 2003, 31 7: 938-944. DOI: 10.1124/dmd.31.7.938
[3] TETSURO AGO. Nifedipine inhibits cardiac hypertrophy and left ventricular dysfunction in response to pressure overload.[J]. Journal of Cardiovascular Translational Research, 2010, 3 4: 304-313. DOI: 10.1007/s12265-010-9182-x
[4] J. LEMAY. Regression of Neointimal Lesions in the Carotid Artery of Nifedipine-Treated SHR and WKY Rats: Possible Role of Apoptosis[J]. Journal of Vascular Research, 2001, 38 1: 462-470. DOI: 10.1159/000051079

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