Amrinon

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H301：Giftig bei Verschlucken.

Amrinone Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R25:Giftig beim Verschlucken.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

• Beschreibung

  Amrinone is a positive inotropic agent useful in the management of severe congestive heart failure. It is effective even in unresponsive, fully digitalized patients.

• Beschreibung

  Amrinone is an inhibitor of phosphodiesterase 3 (PDE3; IC₅₀ = 19.5 μM). It increases developed tension and contractile force in isolated cat papillary muscle. Amrinone (1-10 mg/kg) has positive inotropic effects, increasing the rate and force of heart contraction in anesthetized and unanesthetized dogs.

• Chemische Eigenschaften

  Crystalline Solid

• Originator

  Sterling-Winthrop (USA)

• Verwenden

  Amrinone is used for short-term treatment of cardiac insufficiency that does not respond to treatment of other drugs.

• Verwenden

  analgesic, antipyretic, antiinflammatory

• Verwenden

  A selective cAMP phosphodiesterase (PDE-3) inhibitor with positive inotropic and vasodilatory activity. Cardiotonic

• Definition

  ChEBI: Amrinone is a 3,4'-bipyridine substituted at positions 5 and 6 by an amino group and a keto function respectively. A pyridine phosphodiesterase 3 inhibitor, it is a drug that may improve the prognosis in patients with congestive heart failure. It has a role as an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor.

• Manufacturing Process

  A mixture containing 10g of 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone, 200 ml of dimethylformamide and 1.5 g of 10% palladium-on-charcoal was hydrogenated under pressure (50 psi) at room temperature until the uptake of hydrogen ceased (about 30 minutes). The reaction mixture was filtered through infusorial earth and the filtrate was heated in vacuum to remove the solvent. The residual material was crystallized from dimethylformamide, washed successively with ethanol and ether, and dried in a vacuum oven at 80°C for 8 hours to yield 6 g of 3-amino-5-(4-pyridinyl)-2(1H)-pyridinone, melting point 294° to 297°C with decomposition.

• Trademarks

  Inocor (Sterling Winthrop).

• Therapeutic Function

  Cardiotonic

• Allgemeine Beschreibung

  During normal heart function, cAMP performsimportant roles in regulating intracellular calcium levels.That is, certain calcium channels and storage sites forcalcium must be activated by cAMP-dependant protein kinases.Because cAMP plays an indirect role in the contractilityprocess, agents that inhibit its degradation will providemore calcium for cardiac contraction. One phosphodiesteraseenzyme that is involved in the hydrolysis of myocardiumcAMP is F-III. Amrinone, 5-amino (3,4 -dipyridin)-6 1 (H)-one (Inocor), possesses positive isotropic effects as aresult of its ability to inhibit this phosphodiesterase. In 1999,the USP Nomenclature Committee and the United StatesAdopted Names (USAN) Council approved changing thenonproprietary name and the current official monograph titleof amrinone to inamrinone. This change in nomenclature wasa result of amrinone being confused with amiodarone becauseof the similarity of the names. This was reported to cause confusionbetween the products that led to medication errors,some of which resulted in serious injury or death.

• Sicherheitsprofil

  Poison by ingestion andintravenous routes. Human systemic effects by ingestion:cardiac arrhythmias, liver function, thrombocytopenia. Anexperimental teratogen. Other experimental reproductiveeffects. When heated to decomposition it emits toxicfumes o

• Synthese

  Amrinone, 3-amino-5-(4-piridinyl)-2(1H)-pyridinone (17.2.4), can be synthesized from piridine-4-acetic acid, the reaction of which with a mixture of diemthylformamide?a phosphorous oxychloride gives 2-(4-piridyl)-3-dimethylaminoacrolein (17.2.1). Reacting this with cyanoacetamide gives 3-cyano-5-(4-piridyl)-2(1H)-pyidinone (17.2.2). Hydrolysis of the cyano group of this product gives 3-carbamyl-5-(4-piridyl)-2(1H)-pyidinone (17.2.3). A Hofmann rearrangement of this product (using bromine in sodium hydroxide) gives amrinone (17.2.4).
  An alternative method for the synthesis of amrinone from 3-cyano-5-(4-piridyl)-2(1H)- pyridinone (17.2.2) is based on it?ˉs acidic hydrolysis to the corresponding acid, 3-carboxy- 5-(4-piridyl)-2(1H)-pyridinone (17.2.5), nitration of which with nitrous acid in the presence of sulfuric acid forms 3-nitro-5-(4-piridyl)-2(1H)-pyridinone (17.2.6). Reducing the nitro group of this product with hydrogen gives the desired amrinone (17.2.4).

  

Amrinone Upstream-Materialien And Downstream Produkte

Amrinon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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