1,4-Dihydro-2,6-dimethyl-4-(2-ni-trophenyl)-3,5-pyridindicarbon-säure-dimethylester

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

Nifedipine Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

• Beschreibung

  Nifedipine (21829-25-4) is a clinically useful L-type calcium blocker.

• Chemische Eigenschaften

  Yellow Crystalline Solid

• Originator

  Adalat,Bayer,W. Germany,1975

• Verwenden

  For the management of vasospastic angina, chronic stable angina, hypertension, and Raynaud's phenomenon. May be used as a first line agent for left ventricular hypertrophy and isolated systolic hypertension (long-acting agents).

• Verwenden

  Nifedipine is used for preventing and relieving angina pectoris attacks, for hypertension, and as an ingredient in combination therapy for chronic cardiac insufficiency.

• Verwenden

  Used as an antihypertensive and antianginal. A dihydorpyridine calcium channel blocker

• Definition

  ChEBI: Nifedipine is a dihydropyridine, a methyl ester and a C-nitro compound. It has a role as a calcium channel blocker, a vasodilator agent, a tocolytic agent and a human metabolite.

• Manufacturing Process

  45 grams 2-nitrobenzaldehyde, 80 cc acetoacetic acid methyl ester, 75 cc methanol and 32 cc ammonia are heated under reflux for several hours, filtered off, cooled and, after suction-filtration, 75 grams of yellow crystals of MP 172° to 174°C are obtained, according to US Patent 3,485,847.

• Trademarks

  Adalat (Bayer); Afeditab (Watson);Procardia (Pfizer).

• Therapeutic Function

  Coronary vasodilator

• Weltgesundheitsorganisation (WHO)

  Nifedipine is a dihydropyridine calcium channel blocker. It is listed in the WHO Model List of Essential Drugs. The 10mg tablet is retained on the list for short-term treatment of hypertension. Sustained-release preparations are advised for long-term treatment.

• Allgemeine Beschreibung

  Odorless yellow crystals or powder. Tasteless.

• Allgemeine Beschreibung

  Nifedipine, 1,4-dihydro-2, 6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate dimethyl ester(Adalat, Procardia), is a dihydropyridine derivative thatbears no structural resemblance to the other calcium antagonists.It is not a nitrate, but its nitro group is essential for itsantianginal effect. As a class, the dihydropyridines possessa central pyridine ring that is partially saturated. To this, positions2 and 6 are substituted with an alkyl group that mayplay a role in the agent’s duration of action. In addition, positions3 and 5 are carboxylic groups that must be protectedwith an ester functional group. Depending on the type ofester used at these sites, the agent can be distributed to variousparts of the body. Finally, position 4 requires an aromaticsubstitution possessing an electron-withdrawinggroup (i.e., Cl or NO₂) in the ortho and/or meta position.

• Air & Water Reaktionen

  Aqueous solutions are very sensitive to light. . Insoluble in water.

• Reaktivität anzeigen

  Nifedipine is sensitive to light.

• Brandgefahr

  Flash point data for Nifedipine are not available; however, Nifedipine is probably combustible.

• Biologische Aktivität

  L-type calcium channel blocker.

• Biochem/physiol Actions

  Nifedipine is a L-type Ca2+ channel blocker; and induces apoptosis in human glioblastoma cells. 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). Nifedipine has antihypertensive properties. Nifedipine inhibits extracellular region of adenosine A2a receptor (ADORA2A) gene.

• Mechanism of action

  Nifedipin causes relaxation of smooth musculature, dilation of coronary and peripheral arteries, and reduction of peripheral resistance and arterial blood pressure, and enhances oxygen supply to the heart.

• Clinical Use

  The prototype of this class, nifedipine, has potent peripheralvasodilatory properties. It inhibits the voltage-dependentcalcium channel in the vascular smooth muscle but has littleor no direct depressant effect on the SA or AV nodes, eventhough it inhibits calcium current in normal and isolated cardiactissues. Nifedipine is more effective in patients whoseanginal episodes are caused by coronary vasospasm and isused in the treatment of vasospastic angina as well as classicangina pectoris. Because of its strong vasodilatory properties,it is used in selected patients to treat hypertension.

• Synthese

  Nifedipine, dimethyl ether 1,4-dihydro-2,6-dimethyl-4-(2??-nitrophenyl)-3,5- piridindicarboxylic acid (19.3.16), is synthesized by a Hantsch synthesis from two molecules of a |?-dicarbonyl compound?amethyl acetoacetate, using as the aldehyde component?a 2-nitrobenzaldehyde and ammonia. The sequence of the intermediate stages of synthesis has not been completely established.

  

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Aminophylline: possibly increases aminophylline concentration.
  Anaesthetics: enhanced hypotensive effect.
  Anti-arrhythmics: concentration of dronedarone increased.
  Antibacterials: metabolism accelerated by rifampicin; metabolism possibly inhibited by clarithromycin, erythromycin and telithromycin.
  Antidepressants: metabolism possibly inhibited by fluoxetine; concentration reduced by St John’s wort; enhanced hypotensive effect with MAOIs.
  Antiepileptics: effect reduced by carbamazepine, barbiturates, phenytoin and primidone.
  Antifungals: metabolism possibly inhibited by itraconazole and ketoconazole; concentration increased by micafungin; negative inotropic effect possibly increased with itraconazole.
  Antihypertensives: enhanced hypotensive effect, increased risk of first dose hypotensive effect of post-synaptic alpha-blockers; occasionally severe hypotension and heart failure with beta-blockers.
  Antivirals: concentration possibly increased by ritonavir; use telaprevir with caution.
  Cardiac glycosides: digoxin concentration possibly increased.
  Ciclosporin: may increase ciclosporin level, but not a problem in practice; nifedipine concentration may be increased.
  Cytotoxics: metabolism of vincristine possibly reduced.
  Grapefruit juice: concentration increased - avoid.
  Magnesium salts: profound hypotension with IV magnesium.
  Tacrolimus: increased tacro

• Stoffwechsel

  Nifedipine is metabolised in the gut wall and oxidised in the liver via the cytochrome P450 isoenzyme CYP3A4, to inactive metabolites. Excreted mainly as metabolites via the kidney

• Lager

  +4°C (desiccate)

• Einzelnachweise

  1) Vater et al., (1972), (Pharmacology of 4-(2′-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester (Nifedipine, BAY a 1040); Arzneimittelforschung, 22 1

Nifedipine Upstream-Materialien And Downstream Produkte

1,4-Dihydro-2,6-dimethyl-4-(2-ni-trophenyl)-3,5-pyridindicarbon-säure-dimethylester Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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