Pirenzepine

Identification

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

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGastric ulcer••••••••••••••••••
Treatment ofSmall intestine ulcer••••••••••••••••••
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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
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
PathwayCategory
Pirenzepine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

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.
DrugInteraction
AclidiniumThe risk or severity of adverse effects can be increased when Pirenzepine is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Pirenzepine.
AlfentanilThe risk or severity of adverse effects can be increased when Pirenzepine is combined with Alfentanil.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Pirenzepine.
AmantadineThe risk or severity of adverse effects can be increased when Pirenzepine is combined with Amantadine.
Food Interactions
  • Take on an empty stomach. Take pirenzepine at least 30 minutes before meals.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pirenzepine hydrochloride10YM403FLS29868-97-1FFNMBRCFFADNAO-UHFFFAOYSA-N
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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gastrozepin Tab 50mgTablet50 mg / tabOralBoehringer Ingelheim (Canada) Ltd Ltee1984-12-311996-09-09Canada flag

Categories

ATC Codes
A02BX03 — Pirenzepine
Drug Categories
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
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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
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyridobenzodiazepine (CHEBI:8247)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

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

References

General References
  1. Czepita D: [Fundamentals of modern treatment of myopia]. Ann Acad Med Stetin. 2005;51(2):5-9. [Article]
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
Download (36.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentDiabetes Mellitus / Painful Diabetic Neuropathy (PDN)1
2CompletedTreatmentPainful Diabetic Neuropathy (PDN) / Peripheral neuropathy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral50 MG
TabletOral50 mg / tab
TabletOral
Capsule
TabletOral25 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.6Not Available
Caco2 permeability-6.36ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.682 mg/mLALOGPS
logP1.26ALOGPS
logP0.97Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.78Chemaxon
pKa (Strongest Basic)7.2Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area68.78 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity100.93 m3·mol-1Chemaxon
Polarizability37.11 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9917
Blood Brain Barrier+0.9737
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8101
P-glycoprotein inhibitor IInhibitor0.5362
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterInhibitor0.5983
CYP450 2C9 substrateNon-substrate0.7426
CYP450 2D6 substrateNon-substrate0.5571
CYP450 3A4 substrateSubstrate0.6503
CYP450 1A2 substrateInhibitor0.5788
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.8814
CYP450 3A4 inhibitorNon-inhibitor0.8958
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.946
BiodegradationNot ready biodegradable0.9839
Rat acute toxicity1.8779 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6797
hERG inhibition (predictor II)Non-inhibitor0.5475
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03di-9274000000-86b6dd314412cb49103e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0109000000-5af04abd6e884ecec77a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0129000000-64151795ad36d84f357c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-0719000000-c28dcb1c2e013a70837b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0w29-0489000000-48d254f52927f5ddd17a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-9444000000-9260b4ae9b1a952be315
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1690000000-75cbfc34e557a8d53bd0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.2724498
predicted
DarkChem Lite v0.1.0
[M-H]-194.0423498
predicted
DarkChem Lite v0.1.0
[M-H]-184.12595
predicted
DeepCCS 1.0 (2019)
[M+H]+194.9931498
predicted
DarkChem Lite v0.1.0
[M+H]+194.4382498
predicted
DarkChem Lite v0.1.0
[M+H]+186.48395
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.3747498
predicted
DarkChem Lite v0.1.0
[M+Na]+193.78146
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
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]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:00