Pirenzepine (CED0006081)

Record Information
Version1.0
Creation Date2016-05-22 03:45:07 UTC
Update Date2026-08-20 03:08:34 UTC
Accession NumberCHEM016838
Identification
Common NamePirenzepine
ClassSmall Molecule
Description
Pirenzepine is an organic compound with the formula C19H21N5O2 and an average molecular weight of 351.40 g/mol. Pirenzepine belongs to the 1,4-benzodiazepines, a subclass of benzodiazepines within the organic compounds. In terms of biological activity, it is recorded as an antagonist of the Muscarinic acetylcholine receptor M1 (CHRM1). The compound has been identified in 26 recorded sources across diverse sectors. Within healthcare, pharmaceuticals, and veterinary products, it is used as a drug for acid related disorders, with oral exposure being the recorded route. Other sources include food, food processing, and cookware, specifically in food preservation, the preparation of wort, and fermentation processes for beer. It is also found in building and construction materials such as floors and sunshades awnings or outside screens. Furthermore, it is associated with household cleaning and consumer products, including perfumes within detergents and soaps, pipe accessories, tobacco smoke filters, cigar cigarettes, and non electric simulated smoking devices. Additionally, pirenzepine is found in electrical and electronic equipment, including electric hearing aids, antennas, coils, conductors or conductive bodies characterised by the conductive materials, and cores yokes or armatures.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
11-((4-Methyl-1-piperazinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneChEBI
PirenzepinaChEBI
PirenzepinumChEBI
Dihydrochloride, pirenzepineHMDB
UlcoprotectHMDB
Dolorgiet brand OF pirenzepine dihydrochlorideHMDB
GastrozepinHMDB
Piren basanHMDB
Piren-basanHMDB
Pirenzepin ratiopharmHMDB
Pirenzepin-ratiopharmHMDB
Pirenzepine dihydrochlorideHMDB
GastrotsepinHMDB
PirenzepinHMDB
UlgescumHMDB
CT-Arzneimittel brand OF pirenzepine dihydrochlorideHMDB
Pirenzepin von CTHMDB
Ratiopharm brand OF pirenzepine dihydrochlorideHMDB
Azupharma brand OF pirenzepine dihydrochlorideHMDB
Boehringer ingelheim brand OF pirenzepine dihydrochlorideHMDB
L-S 519HMDB
PyrenzepineHMDB
Sagitta brand OF pirenzepine dihydrochlorideHMDB
Von CT, pirenzepinHMDB
Chemical FormulaC19H21N5O2
Average Molecular Mass351.402 g/mol
Monoisotopic Mass351.170 g/mol
CAS Registry Number28797-61-7
IUPAC Name2-[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
Traditional Namepirenzepine
SMILESCN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1
InChI IdentifierInChI=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)
InChI KeyRMHMFHUVIITRHF-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Pyrido-para-diazepine
  • 1,4-benzodiazepine
  • Alpha-amino acid or derivatives
  • N-piperazineacetamide
  • N-methylpiperazine
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Heteroaromatic compound
  • Cyclic carboximidic acid
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.68 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity100.93 m³·mol⁻¹ChemAxon
Polarizability37.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03di-9274000000-86b6dd314412cb49103eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ik9-0869000000-07871a195a1b07560aafNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2920000000-f203c4e307f7cbb9ccbaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-9730000000-81e7602ee0e57b11f329Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0039000000-eba2d6236adedf16c650Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ik9-0295000000-d2fe7d74f38b69f23111Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xr-1960000000-11b9714bc5655d979a4fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0209000000-abe020ee7c3bd795b260Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w29-1429000000-17de4fa81cf69470057bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03kc-9230000000-b37f79f5ccdc399c3a22Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-6d0cde8b33849d6a8df7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w29-0059000000-c5eade40c8f67c093c19Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-0090000000-ca4cb52f06eeaadb0754Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2656.0Log mg/kg[1500:4700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
242Drugs for acid related disordersHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureMuscarinic acetylcholine receptor M3P08483Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureMuscarinic acetylcholine receptor M4P08485Rattus norvegicusPredicted (SEA)0.0778492
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)1.01204
Click to view 3D structureMuscarinic acetylcholine receptor M3Q8VH26Cavia porcellusPredicted (SEA)0.233548
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)1.94623
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)1.40129
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)0.934191
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)1.71268
Click to view 3D structureMuscarinic acetylcholine receptor DM1P16395Drosophila melanogasterPredicted (SEA)0.0778492
D(1B) dopamine receptor structureClick to view 3D structureD(1B) dopamine receptorP21918HumansPredicted (SEA)67.4953
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)105.019
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)113.271
Click to view 3D structureMuscarinic acetylcholine receptor M1Q8WMX0Bos taurusPredicted (SEA)3.65891
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)351.645
Maternal embryonic leucine zipper kinase structureClick to view 3D structureMaternal embryonic leucine zipper kinaseQ14680HumansPredicted (SEA)276.287
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)418.44
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)274.808
Click to view 3D structureD(1A) dopamine receptorP18901Rattus norvegicusPredicted (SEA)114.127
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)270.915
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)432.997
Calcium/calmodulin-dependent protein kinase kinase 2 structureClick to view 3D structureCalcium/calmodulin-dependent protein kinase kinase 2Q96RR4HumansPredicted (SEA)150.015
Click to view 3D structureNUAK family SNF1-like kinase 1O60285HumansPredicted (SEA)128.373
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)401.001
Concentrations
Not Available
External Links
DrugBank IDDB00670
HMDB IDHMDB0014808
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPirenzepine
Chemspider ID4682
ChEBI ID8247
PubChem Compound ID4848
Kegg Compound IDC07508
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Czepita D: [Fundamentals of modern treatment of myopia]. Ann Acad Med Stetin. 2005;51(2):5-9.