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| | Pirenzepine Basic information |
| Product Name: | Pirenzepine | | Synonyms: | PIRENZEPINE DIHYDROCHLORIDE MONOHYDRATE;5，11-Dihydro-11-[(4-methylpiperazin-1-y1)acetyl]-6H-pyrido[2，3-b][1，4]benzodiazepin-6-one;LS-519-C12;Tabe：Ulcuforton;5,11-Dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one;11-((4-methyl-1-piperazinyl)acetyl)-5,11-dihydro-6h-pyrido(2,3-b)(1,4)benzod;5,11-dihydro-11-((4-methyl-1-piperazinyl)acetyl)-6h-pyrido(2,3-b)(1,4)benzod;6h-pyrido(2,3-b)(1,4)benzodiazepin-6-one,5,11-dihydro-11-((4-methyl-1-piperazi | | CAS: | 28797-61-7 | | MF: | C19H21N5O2 | | MW: | 351.4 | | EINECS: | 249-228-4 | | Product Categories: | Muscarinic;EXELDERM | | Mol File: | 28797-61-7.mol |  |
| | Pirenzepine Chemical Properties |
| Boiling point | 541.7±50.0 °C(Predicted) | | density | 1.271±0.06 g/cm3(Predicted) | | storage temp. | Store at RT | | solubility | soluble in No data available | | pka | 11.29±0.20(Predicted) |
| | Pirenzepine Usage And Synthesis |
| Chemical Properties | solid | | Originator | Microsules Bernabo, Microsules Bernabo | | Uses | 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. | | Uses | antifungal | | 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 | | Biological Activity | M 1 muscarinic receptor selective antagonist. Inverse agonist activity reported. | | Enzyme inhibitor | 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 Preparation Products And Raw materials |
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