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Identification
NamePirenzepine
Accession NumberDB00670  (APRD00515)
TypeSmall Molecule
GroupsApproved
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
Synonyms
11-((4-Methyl-1-piperazinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one
Pirenzepin
Pirenzepina
Pirenzépine
Pirenzepinum
External Identifiers
  • L-S519
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gastrozepin Tab 50mgtablet50 mgoralBoehringer Ingelheim (Canada) Ltd Ltee1984-12-311996-09-09Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AnquweiPanion & BF
FolinzepinTsuruhara Seiyaku
GarendopineChoseido Pharmaceutical
GaspinGentle
GastrozepinBoehringer Ingelheim
GastsionShiono Kemikaru
GaszepinSwiss Pharm
KaroderinNippon Chemiphar
KawaipinSiu Guan
KiccalzinTakata Seiyaku
LizepineHealth Chemical
LonzepinLi Ta
MuszepinRoyal
PilenzelTaiyo Pharmaceutical
PinTatsumi Kagaku
PirepineYu Sheng
PirodeineMedisa Shinyaku
PizepineYuan Chou
RanclicTowa Yakuhin
RegastricJinup
StomazepinTaisho Yakuhin
UlopinePanbiotic
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pirenzepine Hydrochloride
ThumbNot applicableDBSALT001002
Categories
UNII3G0285N20N
CAS number28797-61-7
WeightAverage: 351.4023
Monoisotopic: 351.169524941
Chemical FormulaC19H21N5O2
InChI KeyInChIKey=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[9.4.0.0³,⁸]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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Pyrido-para-diazepine
  • N-piperazineacetamide
  • Alpha-amino acid or derivatives
  • N-alkylpiperazine
  • N-methylpiperazine
  • Para-diazepine
  • Imidolactam
  • Benzenoid
  • Pyridine
  • Piperazine
  • 1,4-diazinane
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary carboxylic acid amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of peptic ulcer, gastric ulcer, and duodenal ulcer.
PharmacodynamicsPirenzepine 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 actionPirenzepine 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Pirenzepine Action PathwayDrug actionSMP00246
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tabletoral50 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.6Not Available
Caco2 permeability-6.36ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.682 mg/mLALOGPS
logP1.26ALOGPS
logP0.85ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.57ChemAxon
pKa (Strongest Basic)7.59ChemAxon
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Czepita D: [Fundamentals of modern treatment of myopia]. Ann Acad Med Stetin. 2005;51(2):5-9. [PubMed:16519089 ]
External Links
ATC CodesA02BX03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (36.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
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. [PubMed:11752352 ]
  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:12717096 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23