2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

• ChemBase ID: 552
• Molecular Formular: C19H21N5O2
• Molecular Mass: 351.40234
• Monoisotopic Mass: 351.16952494
• SMILES: O=C(n1c2c(c(=O)[nH]c3c1nccc3)cccc2)CN1CCN(CC1)C
• Canonical SMILES: CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
• InChI: InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)
• InChIKey: RMHMFHUVIITRHF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one; 2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• IUPAC Traditional name: pirenzepine; 2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• Brand Name: Bisvanil; Gasteril; Gastrozepin; Leblon; Pirenzepin; Pirenzepina [INN-Spanish]; Pirenzepine Gastrozepin; Pirenzepinum [INN-Latin]; Tabe; Ulcosan
• Synonyms: Pirenzepine; Pirenzepine; 5,11-Dihydro-11-[2-(4-methyl-1-piperazinyl)acetyl]-6H-pyrido[2,3-b][1,4]benzo-diazepin-6-one Dihydrochloride; Duogastral; Durapirenz; Gasteril; Gastrozepin; Leblon; Maghen; Renzepin; Tabe; Ulcuforton; Ulcosan; Pirenzepine, Dihydrochloride

Database IDs

• CAS Number: 28797-61-7; 29868-97-1
• PubChem SID: 46509029; 160964015
• PubChem CID: 4848

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.574185
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.1168518
• LogD (pH = 7.4): 0.55378336
• Log P: 0.85245126
• Molar Refractivity: 100.9257 cm^3
• Polarizability: 37.71037 Å^3
• Polar Surface Area: 68.78 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.26
• LOG S: -2.71
• Solubility (Water): 6.82e-01 g/l

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Solid
• Melting Point: 248-250°C
• Hydrophobicity(logP): 0.6

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Mechanism of Action: Muscarine M 1 receptor antagonist; Parasympatholytic; Spasmolytic

Product Information

• Application(s): Antiemetic; Spasmolytic; Used for gastric ulcer treatment

DETAILS

DrugBank - DB00670

• Drug Groups: approved
• Description: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as cimetidine and ranitidine. It is generally well tolerated by patients. [PubChem]
• Indication: For the treatment of peptic ulcer, gastric ulcer, and duodenal ulcer.
• Pharmacology: Pirenzepine belongs to a group of medications called antispasmodics/anticholinergics. These medications are used to relieve cramps or spasms of the stomach, intestines, and bladder. Pirenzepine is used to treat duodenal or stomach ulcers or intestine problems. It can be used together with antacids or other medicine in the treatment of peptic ulcer. It may also be used to prevent nausea, vomiting, and motion sickness.
• Affected Organisms: Humans and other mammals
• References: Czepita D: [Fundamentals of modern treatment of myopia] Ann Acad Med Stetin. 2005;51(2):5-9. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - P508500

An antiulcerative. Tricyclic gastric-acid inhibitor.

REFERENCES

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