67035-22-7

Basic information

• Product Name: OXIDIZED NIFEDIPINE
• Synonyms: dimethyl2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate;2,6-Dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3,5-Dimethyl Ester;B 4759;Dehydro Nifedipine;2,6-Dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylic acid dimethyl ester;4-(2-Nitrophenyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid dimethyl ester;BAY-b-4759;Nitrophenyl nifedipine
• CAS NO: 67035-22-7
• Molecular Formula: C₁₇H₁₆N₂O₆
• Molecular Weight: 344.31874
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 67035-22-7.mol

Chemical Properties

• Melting Point: 100-105 °C
• Boiling Point: 443.7°Cat760mmHg
• Flash Point: 222.1°C
• Appearance: yellow/powder
• Density: 1.284g/cm³
• Vapor Pressure: 4.54E-08mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 1.55±0.29(Predicted)
• CAS DataBase Reference: OXIDIZED NIFEDIPINE(CAS DataBase Reference)
• NIST Chemistry Reference: OXIDIZED NIFEDIPINE(67035-22-7)
• EPA Substance Registry System: OXIDIZED NIFEDIPINE(67035-22-7)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 2
• Hazardous Substances Data: 67035-22-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Oxidized Nifedipine is used as an active metabolite for the treatment of hypertension and angina. It plays a significant role in the therapeutic effects of Nifedipine formulations by blocking calcium channels, leading to vasodilation and reduced blood pressure.
Used in Neurological Research:
Oxidized Nifedipine is used as a research tool for apoptotic signaling studies in dopaminergic neurons. This application helps in understanding the underlying mechanisms of neurodegenerative diseases and the potential therapeutic effects of Nifedipine and its metabolites in such conditions.
Used in Human Plasma Analysis:
As the main Nifedipine metabolite in human plasma, Oxidized Nifedipine is used for monitoring the metabolism and pharmacokinetics of Nifedipine in patients. This information is crucial for optimizing dosages and ensuring the safety and efficacy of Nifedipine treatment.

Biochem/physiol Actions

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

InChI:InChI=1/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

Upstream product

• 21829-25-4 nifedipine 
• 105-45-3 acetoacetic acid methyl ester 
• 119777-23-0 C₁₇H₁₈N₂O₆*C₄₂H₇₀O₃₅ 
• 552-89-6 2-nitro-benzaldehyde 
• 14205-39-1 methyl 3-aminocrotonate 

Downstream Products

• 34785-00-7 2-Methyl-4-(2-nitrophenyl)-5-oxo-5,7-dihydrofuro<3,4-b>pyridin-3-carbonsaeuremethylester 
• 73372-63-1 Oxidized Nifedipine Monomethylester 
• 88434-67-7 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylic acid 

Relevant articles and documents

Efficient drug metabolism strategy based on microsome-mesoporous organosilica nanoreactors

A rapid and accurate in vitro drug metabolism strategy has been proposed based on the design of a biomimetic nanoreactor composed of amino-functionalized periodic mesoporous organosilica (NH2-PMO) and microsomes. The amphiphilic nature and posi

A highly selective H/D exchange reaction of 1,4-dihydropyridines

Herein, we report a simple, economical, and effective acid-mediated method for the in situ deuteration of Hantzsch esters and their 4-substituted derivatives, including some drugs that constitute important calcium channel blockers which are effective for

CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies

CO2-catalyzed dehydrogenation of amines has been achieved under photocatalytic conditions. With this concept, various amines have been selectively dehydrogenated to the corresponding imines in the presence of different functional groups such as nitrile, nitro, ester, halogen, ether, thioether, and carbonyl or carboxylic acid moieties. At the end, the CO2-catalyzed synthesis of pharmaceutical drugs has been achieved. The CO2 radical has been detected by EPR spectroscopy using DMPO, and the mechanism of this reaction is proposed on the basis of DFT calculations and experimental evidence.

Dihydropyridine compound dehydrogenation aromatization method and in use in the drug detection (by machine translation)

Relates to dihydropyridine compound dehydrogenation aromatization method and in use in the drug detection, compounds such as nifedipine, amlodipine, Cini horizontal, Lacidipine, felodipine, NIKA of amlodipine, nitrendipine, nimodipine and BANI to equal, the method in acidic aqueous solution in the presence of a nickel-containing catalyst in the oxidation reaction of the then purified to realize. The method can be used for preparing this kind of drug detection and quality monitoring of the impurity reference substance, also can be used for quality detection process is used in the instrument of the instrument such as the dissolution of the design reference, drug synthesis process and the design of the manufacturing process of the preparation of the reference, in order to avoid impurities introduced by the process channels, in addition can also be dihydropyridine compound of related synthetic process route provides design provides a reference. The reaction can be in the acidic aqueous solution, to a suitable oxidant (such as air) as the oxidizing agent, in the presence of nickel, at normal temperature to carry out dehydrogenation aromatization reaction, mild reaction conditions, the target compound of high conversion rate, the operation is simple, by-product little small pollution to the environment, is a completely environment-friendly preparation process. (by machine translation)

N3,N6-BIS(2-(5-METHOXY-1H-INDOLE-3-YL)ETHYL)-2,6-DIMETHYL-4-(2-NITROPHENYL)PYRIDINE-3,5-DICARBOXAMIDE AND USE THEREOF IN THE FIELD OF NEUROTOXICITY

The invention relates to a molecule enabling removal of neurotoxicity observed in neuron cells due to various reasons.

For 1, 4 - dihydro pyridine compound to prepare the corresponding pyridine compound (by machine translation)

The invention discloses a method for the 1, 4 - dihydro pyridine compound to prepare the corresponding pyridine compound. The method of the invention is: will be 1, 4 - dihydro pyridine compound, eosin Y of the four n-butyl ammonium salt, potassium carbonate is added to the organic solvent with the water in the mixed solvent of stirring and mixing, inject the air in visible light irradiation under the conditions of reaction, to be after the reaction, by adding ethyl acetate, respectively water, saturated ammonium chloride washing, removal of inorganic alkali and adjust the system to subacid, in the organic phase by adding a small amount of activated carbon to remove the pigment, then dried with anhydrous sodium sulfate, turns on lathe does, recrystallize and obtain the corresponding pyridine compound. The method of the invention compared with the prior art has to oxygen in air as the oxidizing agent, is cheap and easy to get; to sunlight as the energy source, so that the industrial production more favorable; catalytic amount of the use of non-metal catalyst, reduces the cost of synthesizing, avoiding the noble metal in the accumulation of drug in the synthesis. (by machine translation)

Acetylshikonin is a novel non-selective cytochrome P450 inhibitor

Acetylshikonin is a biologically active compound with anti-cancer and anti-inflammatory activity, which is isolated from the roots of Lithospermum erythrorhizoma. An inhibitory effect of acetylshikonin against CYP2J2 activity was discovered recently. Based on this result, this study was expanded to evaluate the inhibitory effects of acetylshikonin against nine different cytochrome P450 (P450) isoforms in human liver microsomes (HLMs) using substrate cocktails incubation assay. Acetylshikonin showed a strong inhibitory effect against all P450s tested with IC50 values of 1.4–4.0 μ m. Pre-incubation of acetylshikonin with HLMs and NADPH did not alter the inhibition potency, indicating that acetylshikonin is not a mechanism-based inhibitor. SKF-525A, a widely used non-specific P450 inhibitor, had no inhibitory activity against CYP1A2, 2A6, 2E1 and 2J2, while it showed an inhibitory effect against CYP2B6, CYP2C19 and 2D6 with IC50 values of 2.5, 3.6 and 0.5 μ m, respectively. Our findings indicate that acetylshikonin may be a novel general P450 inhibitor, which could replace SKF-525A.

Study of temperature dependent three component dynamic covalent assembly VIa Hantzsch reaction catalyzed by dioxido- and oxidoperoxidomolybdenum(VI) complexes under solvent free conditions

Tridentate ONO donor ligands derived from heterocyclic compound 4-acetyl-3-methyl-1-phenyl-2-pyrazoline-5-one (Hap) and aromatic hydrazides {benzoyl hydrazide (Hbhz), isonicotinoyl hydrazide (Hinh), nicotinoyl hydrazide (Hnah) and furoyl hydrazide (Hfah)} react with [MoVIO2(acac)2] (Hacac = acetylacetone) in equimolar ratio in methanol to give dioxidomolybdenum(vi) complexes, [MoO2(ap-bhz)(MeOH)] 1, [MoO2(ap-inh)(MeOH)] 2, [MoO2(ap-nah)(MeOH)] 3 and [MoO2(ap-fah)(MeOH)] 4. Reaction of these ligands with in situ generated oxidoperoxidomolybdenum(vi) precursor results in the formation of oxidoperoxidomolybdenum(vi) complexes, [MoO(O2)(ap-bhz)(MeOH)] 5, MoO(O2)(ap-inh)(MeOH)] 6, MoO(O2)(ap-nah)(MeOH)] 7 and MoO(O2)(ap-fah)(MeOH)] 8. These complexes have been characterized by elemental analysis, spectroscopic techniques (infrared, UV-vis, 1H and 13C NMR) and thermogravemetric analysis. The structures of complexes [MoVIO2(ap-bhz)(H2O)] 1a (water coordinated), [MoVIO2(ap-bhz)(DMSO)] 1b (DMSO coordinated), [MoVIO2(ap-nah)(DMF)] 3a (DMF coordinated), [MoVIO(O2)(ap-bhz)(MeOH)] 5 (methanol coordinated) and [MoVIO(O2)(Hap-nah)(OMe)]·MeOH 7a (methoxy coordinated) have been confirmed by single crystal X-ray studies. X-ray diffraction study also reveals that tridentate ligands bind to the metal center through enolic oxygen (of pyrazolol), azomethine nitrogen and enolic oxygen (of hydrazide) atoms. In complex 7a, pyridinic nitrogen is protonated. These complexes [dioxidomolybdenum(vi) as well as oxidoperoxidomolybdenum(vi)] have been tested as catalysts for temperature dependent one pot three component (methylacetoacetate, benzaldehyde and ammonium acetate) dynamic covalent assembly, via Hantzsch reaction, using 30% H2O2 as a green oxidant under solvent free conditions. Various parameters such as the amount of catalyst, oxidant and temperature of the reaction mixture have been taken into consideration to optimize the reaction conditions. In the Hantzsch reaction, the temperature and oxidant control the conversion and selectivity of the desired product.

Metal-free-mediated oxidation aromatization of 1,4-dihydropyridines to pyridines using visible light and air

A metal-free and environmentally friendly aerobic aromatization photosensitized by organic dye eosin Y bis(tetrabutyl ammonium salt) (TBA-eosinY) has been developed. With the aid of K2CO3, the aerobic catalytic system converts 1,4-dihydropyridines to their corresponding pyridine derivatives efficiently under visible light irradiation (λ=450 nm) at room temperature.

Structure-function analysis of porcine cytochrome P450 3A29 in the hydroxylation of T-2 toxin as revealed by docking and mutagenesis studies

T-2 toxin, one of the type A trichothecenes, presents a potential hazard to human and animal health. Our previous work demonstrated that porcine cytochrome P450 3A29 (CYP3A29) played an important role in the hydroxylation of T-2 toxin. To identify amino a