Pirenzepine

Pirenzepine Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  Pirenzepine is available as dihydrochloride monohydrate, soluble in water. Because of its unfavorable balance between weak antisecretory and frequent anticholinergic adverse effects (dry mouth, blurred vision), pirenzepine is considered obsolete .

• Chemische Eigenschaften

  solid

• Originator

  Microsules Bernabo, Microsules Bernabo

• Verwenden

  antifungal

• Verwenden

  Pirenzepine, is an M1 selective antagonist, that is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm.

• Definition

  ChEBI: Pirenzepine is a pyridobenzodiazepine. It has a role as an anti-ulcer drug, a muscarinic antagonist and an antispasmodic drug.

• Manufacturing Process

  48.4 g of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzo-diazepin-6-one were refluxed in 900 ml of absolute dioxane for 15 minutes. Thereafter, over a period of 45 minutes, 28 ml of chloroacetyl chloride and 52 ml of triethylamine were simultaneously added dropwise to the mixture. The mixture was refluxed for eight hours and then vacuum-filtered after having cooled. The filtrate was evaporated in vacuum. The crystalline residue was recrystallized from acetonitrile in the presence of activated charcoal. MP: 212°-213°C (with decomposition). Yield: 85% of theory.
  A mixture of 67.5 g of 11-chloroacetyl-5,11-dihydro-6H-pyrido[2,3b][1,4]benzodiazepin-6-one, 183 ml of N-methylpiperazine and 1.37 liters of absolute benzene was refluxed for 18 hours. Thereafter, the crystalline precipitate was vacuum filtered off, dissolved in aqueous 20% hydrochloric acid, the solution was evaporated in vacuum, the crystalline residue wasdissolved in 250 ml of water while heating, the solution was admixed with 150 ml of isopropanol and active charcoal, filtered, and 2.5 liters of isopropanol were added to the filtrate. After cooling, the precipitate was vacuum filtered off, yielding 70% of theory of the 5,11-dihydro-11-[(4'-methyl-1'-piperazinyl)acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one dihydrochloride, M.P. 257259°C (decomp.).
  The free base of pirenzepine, obtained from the dihydrochloride by making an aqueous solution thereof alkaline with dilute sodium hydroxide and extracting it with chloroform, had MP: 226°-228°C after recrystallization from methanol/ether.

• Therapeutic Function

  Antiulcer, Antiemetic

• Biologische Aktivität

  M 1 muscarinic receptor selective antagonist. Inverse agonist activity reported.

• Enzyminhibitor

  This hygroscopic antiulcerative (FWfree-base = 351.41 g/mol; CAS 28797-61- 7) is a gastric acid inhibitor and selective M1 muscarinic receptor antagonist, and the antisecretory properties of pirenzepine on gastric acid and pepsin secretion may be attributed to this antagonistic activity on muscarinic M1 receptors.

Pirenzepine Upstream-Materialien And Downstream Produkte

Pirenzepine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(60)Suppliers

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