NAV

Pirenzepine

Identification

Summary

Pirenzepineis 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
 3D
Similar Structures
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
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.

Target Actions 生物
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
Pathway Category
Pirenzepine Action Pathway Drug action
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
Drug Interaction
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interactions in your software
Aclidinium The risk or severity of adverse effects can be increased when Pirenzepine is combined with Aclidinium.
Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Pirenzepine.
Alfentanil The risk or severity of adverse effects can be increased when Pirenzepine is combined with Alfentanil.
Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Pirenzepine.
Amantadine The risk or severity of adverse effects can be increased when Pirenzepine is combined with Amantadine.
Ambenonium The therapeutic efficacy of Pirenzepine can be decreased when used in combination with Ambenonium.
Amitriptyline The risk or severity of adverse effects can be increased when Pirenzepine is combined with Amitriptyline.
Amitriptylinoxide The risk or severity of adverse effects can be increased when Pirenzepine is combined with Amitriptylinoxide.
Amobarbital The risk or severity of adverse effects can be increased when Pirenzepine is combined with Amobarbital.
Amoxapine The risk or severity of adverse effects can be increased when Pirenzepine is combined with Amoxapine.
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Food Interactions
  • Take on an empty stomach. Take pirenzepine at least 30 minutes before meals.

Products

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Product Ingredients
Ingredient UNII CAS InChI Key
Pirenzepine hydrochloride 10YM403FLS 29868-97-1 FFNMBRCFFADNAO-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)
品牌名称的处方产品
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 Canada flag

Categories

ATC Codes
A02BX03 — Pirenzepine
Drug Categories
Chemical TaxonomyProvided byClassyfire
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
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
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

一般引用
  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 TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
2 Completed Treatment Diabetes Mellitus/Painful Diabetic Neuropathy (PDN) 1
2 Completed Treatment Painful Diabetic Neuropathy (PDN)/Peripheral neuropathy 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Form Route Strength
Tablet Oral 50 mg / tab
Tablet Oral
Capsule
Tablet Oral 25 mg
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 0.682 mg/mL ALOGPS
logP 1.26 ALOGPS
logP 0.97 Chemaxon
logS -2.7 ALOGPS
pKa (Strongest Acidic) 14.78 Chemaxon
pKa (Strongest Basic) 7.2 Chemaxon
Physiological Charge 1 Chemaxon
Hydrogen Acceptor Count 5 Chemaxon
Hydrogen Donor Count 1 Chemaxon
Polar Surface Area 68.78 Å2 Chemaxon
Rotatable Bond Count 2 Chemaxon
Refractivity 100.93 m3·mol-1 Chemaxon
Polarizability 37.11 Å3 Chemaxon
Number of Rings 4 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule No Chemaxon
MDDR-like Rule No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9917
Blood Brain Barrier + 0.9737
Caco-2 permeable - 0.8957
P-glycoprotein substrate Substrate 0.8101
P-glycoprotein inhibitor I Inhibitor 0.5362
P-glycoprotein inhibitor II Non-inhibitor 0.8383
Renal organic cation transporter Inhibitor 0.5983
CYP450 2C9 substrate Non-substrate 0.7426
CYP450 2D6 substrate Non-substrate 0.5571
CYP450 3A4 substrate Substrate 0.6503
CYP450 1A2 substrate Inhibitor 0.5788
CYP450 2C9 inhibitor Non-inhibitor 0.9071
CYP450 2D6 inhibitor Non-inhibitor 0.9231
CYP450 2C19 inhibitor Non-inhibitor 0.8814
CYP450 3A4 inhibitor Non-inhibitor 0.8958
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682
Ames test Non AMES toxic 0.5
Carcinogenicity Non-carcinogens 0.946
Biodegradation Not ready biodegradable 0.9839
Rat acute toxicity 1.8779升D50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6797
hERG inhibition (predictor II) Non-inhibitor 0.5475
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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insights and accelerate drug research.
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Details 1.Muscarinic acetylcholine receptor M1
Kind
Protein
生物
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
磷脂酰肌醇磷脂酶c活动
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
分子量
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 March 03, 2023 17:47