Pirenzepine (original) (raw)

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Summary

Pirenzepine is an antimuscarinic agent used to treat peptic ulcers, gastric ulcers, and duodenal ulcers.

Generic Name

Pirenzepine

DrugBank Accession Number

DB00670

Background

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.

Type

Small Molecule

Groups

Approved

Structure

Weight

Average: 351.4023
Monoisotopic: 351.169524941

Chemical Formula

C19H21N5O2

Synonyms

• 11-((4-Methyl-1-piperazinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one
• Pirenzepin
• Pirenzepina
• Pirenzépine
• Pirenzepine
• Pirenzepinum

External IDs

• ACI-91
• L-S519

Indication

For the treatment of peptic ulcer, gastric ulcer, and duodenal ulcer.

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Associated Conditions

Contraindications & Blackbox Warnings

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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

Adverse Effects

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Toxicity

Not Available

Pathways

Pharmacogenomic Effects/ADRs

Not Available

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Food Interactions

• Take on an empty stomach. Take pirenzepine at least 30 minutes before meals.

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Product Ingredients

International/Other Brands

Anquwei (Panion & BF) / Folinzepin (Tsuruhara Seiyaku) / Garendopine (Choseido Pharmaceutical) / Gaspin (Gentle) / Gastrozepin (Boehringer Ingelheim) / Gastsion (Shiono Kemikaru) / Gaszepin (Swiss Pharm) / Karoderin (Nippon Chemiphar) / Kawaipin (Siu Guan) / Kiccalzin (Takata Seiyaku) / Lizepine (Health Chemical) / Lonzepin (Li Ta) / Muszepin (Royal) / Pilenzel (Taiyo Pharmaceutical) / Pin (Tatsumi Kagaku) / Pirepine (Yu Sheng) / Pirodeine (Medisa Shinyaku) / Pizepine (Yuan Chou) / Ranclic (Towa Yakuhin) / Regastric (Jinup) / Stomazepin (Taisho Yakuhin) / Ulopine (Panbiotic)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Gastrozepin Tab 50mg	Tablet	50 mg / tab	Oral	Boehringer Ingelheim (Canada) Ltd Ltee	1984-12-31	1996-09-09

ATC Codes

A02BX03 — Pirenzepine

• A02BX — Other drugs for peptic ulcer and gastro-oesophageal reflux disease (GORD)
• A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
• A02 — DRUGS FOR ACID RELATED DISORDERS
• A — ALIMENTARY TRACT AND METABOLISM

Drug Categories

• Agents producing tachycardia
• Alimentary Tract and Metabolism
• Anti-Ulcer Agents
• Anticholinergic Agents
• Benzazepines
• Benzodiazepinones
• Cholinergic Agents
• Drugs for Acid Related Disorders
• Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
• Gastrointestinal Agents
• Heterocyclic Compounds, Fused-Ring
• Muscarinic Antagonists
• Neurotransmitter Agents

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Pyridodiazepines / Alpha amino acids and derivatives / N-piperazineacetamides / N-methylpiperazines / Benzenoids / Pyridines and derivatives / Imidolactams / Tertiary carboxylic acid amides / Cyclic carboximidic acids / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Propargyl-type 1,3-dipolar organic compounds / Hydrocarbon derivatives / Carbonyl compounds / Organopnictogen compounds / Organic oxides show 7 more

Substituents

1,4-benzodiazepine / 1,4-diazinane / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclic carboximidic acid / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / N-alkylpiperazine / N-methylpiperazine / N-piperazineacetamide / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Piperazine / Propargyl-type 1,3-dipolar organic compound / Pyridine / Pyrido-para-diazepine / Tertiary aliphatic amine / Tertiary amine / Tertiary carboxylic acid amide show 22 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyridobenzodiazepine (CHEBI:8247)

Affected organisms

• Humans and other mammals

UNII

3G0285N20N

CAS number

28797-61-7

InChI Key

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)

IUPAC Name

2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

SMILES

CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1

General References

1. Czepita D: [Fundamentals of modern treatment of myopia]. Ann Acad Med Stetin. 2005;51(2):5-9. [Article]

External Links

Human Metabolome Database

HMDB0014808

KEGG Drug

D08389

KEGG Compound

C07508

PubChem Compound

4848

PubChem Substance

46509029

ChemSpider

4682

BindingDB

39341

RxNav

8352

ChEBI

8247

ChEMBL

CHEMBL9967

ZINC

ZINC000019632927

Therapeutic Targets Database

DAP000492

PharmGKB

PA10159

Wikipedia

Pirenzepine

MSDS

Clinical Trials

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Preview package

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Prices

Not Available

Patents

Not Available

State

Solid

Experimental Properties

Predicted Properties

Predicted ADMET Features

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Mass Spec (NIST)

Not Available

Spectra

Chromatographic Properties

Collision Cross Sections (CCS)

Targets

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Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

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.

Specific Function

G protein-coupled acetylcholine receptor activity

Gene Name

CHRM1

Uniprot ID

P11229

Uniprot Name

Muscarinic acetylcholine receptor M1

Molecular Weight

51420.375 Da

References

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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. [Article]
3. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 03, 2024 10:12