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28797-61-7 molecular structure
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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 and InChIs

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

Cite this record

CBID:552 http://www.chembase.cn/molecule-552.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[9.4.0.03,8]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[9.4.0.03,8]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
CAS Number
28797-61-7
29868-97-1
PubChem SID
160964015
46509029
PubChem CID
4848

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.574185  H Acceptors
H Donor LogD (pH = 5.5) -1.1168518 
LogD (pH = 7.4) 0.55378336  Log P 0.85245126 
Molar Refractivity 100.9257 cm3 Polarizability 37.71037 Å3
Polar Surface Area 68.78 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.26  LOG S -2.71 
Solubility (Water) 6.82e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Water expand Show data source
Apperance
Solid expand Show data source
Melting Point
248-250°C expand Show data source
Hydrophobicity(logP)
0.6 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Mechanism of Action
Muscarine M 1 receptor antagonist expand Show data source
Parasympatholytic expand Show data source
Spasmolytic expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiemetic expand Show data source
Spasmolytic expand Show data source
Used for gastric ulcer treatment expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00670 external link
Item Information
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 external link
An antiulcerative. Tricyclic gastric-acid inhibitor.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Czepita D: [Fundamentals of modern treatment of myopia] Ann Acad Med Stetin. 2005;51(2):5-9. Pubmed
  • • Eberlein, W., et al.: Arzneimittel-Forsch., 27, 356 (1977)
  • • Hellerr, G., et al.: Verh. Deut. Ges. Inn. Med., 84, 991 (1977)
  • • Carmine, A.A., et al.: Drugs, 30,85 (1977)
  • • El-Obeid, H.A., et al.: Anal. Profiles Drug Subs., 16, 445 (1977)
  • • Homon, C.A., et al.
  • • South African Pat., 1970, 69 05 933; CA, 73, 77292m, (synth, pharmacol)
  • • Eberlein, W. et al., Arzneim.-Forsch., 1977, 27, 356; 684, (pharmacol)
  • • Ruzic-Toros, Z. et al., Acta Cryst. C, 1983, 39, 93, (cryst struct)
  • • Kovac, T. et al., J. Het. Chem., 1983, 20, 1339, (synth)
  • • Feng, J. et al., CA, 1984, 101, 110880, (synth)
  • • Bechtel, W.D. et al., Arzneim.-Forsch., 1986, 36, 793, (pharmacol)
  • • El-Obeid, H.A. et al., Anal. Profiles Drug Subst., 1987, 16, 445, (rev, synth, anal, pharmacol)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5258
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 430
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GCE500
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PATENTS

PATENTS

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INTERNET

INTERNET

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