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Identification
Name Pirenzepine
Accession Number DB00670 (APRD00515)
Type small molecule
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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Bisvanil
Gasteril
Gastrozepin
Leblon
Pirenzepin
Pirenzepina [INN-Spanish]
Pirenzepine Gastrozepin
Pirenzepinum [INN-Latin]
Tabe
Ulcosan
Brand mixtures Not Available
Categories
  • Anti-Ulcer Agents
  • Muscarinic Antagonists
  • Antispasmodics
  • Antimuscarinics
CAS number 28797-61-7
Weight Average: 351.4023
Monoisotopic: 351.169524941
Chemical Formula C19H21N5O2
InChI Key InChIKey=RMHMFHUVIITRHF-UHFFFAOYSA-N
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)
Plain Text
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
SMILES
CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzodiazepines
  • Lactams
Substructures
  • Benzodiazepines
  • Amino Ketones
  • Pyridines and Derivatives
  • Piperazines
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
  • Aminopyridines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Benzoyl Derivatives
  • Benzamides
  • Anilines
Pharmacology
Indication For the treatment of peptic ulcer, gastric ulcer, and duodenal ulcer.
Pharmacodynamics 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.
Mechanism of action Pirenzepine is a muscarinic receptor antagonist and binds to the muscarinic acetylcholine receptor. The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00246 Pirenzepine Pathway SMP00246
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 0.6 Not Available
Caco2 permeability -6.36 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 6.82e-01 g/l ALOGPS
logP 1.26 ALOGPS
logP 0.85 ChemAxon
logS -2.7 ALOGPS
pKa (strongest acidic) 9.57 ChemAxon
pKa (strongest basic) 7.59 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 68.78 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 100.93 ChemAxon
polarizability 37.11 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Czepita D: [Fundamentals of modern treatment of myopia] Ann Acad Med Stetin. 2005;51(2):5-9. Pubmed
External Links
Resource Link
KEGG Compound C07508 Link_out
PubChem Compound 4848 Link_out
PubChem Substance 46509029 Link_out
ChemSpider 4682 Link_out
ChEBI 8247 Link_out
ChEMBL 8247 Link_out
Therapeutic Targets Database DAP000492 Link_out
PharmGKB PA10159 Link_out
Drug Product Database 608998 Link_out
Wikipedia http://en.wikipedia.org/wiki/Pirenzepine Link_out
ATC Codes
  • A02BX03
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (36.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take 30 minutes before breakfast and at bedtime.
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Pedretti RF, Prete G, Foreman RD, Adamson PB, Vanoli E: Autonomic modulation during acute myocardial ischemia by low-dose pirenzepine in conscious dogs with a healed myocardial infarction: a comparison with beta-adrenergic blockade. J Cardiovasc Pharmacol. 2003 May;41(5):671-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19