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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:22 UTC
HMDB IDHMDB0014808
Secondary Accession Numbers
  • HMDB14808
Metabolite Identification
Common NamePirenzepine
DescriptionPirenzepine, also known as ulcoprotect or gastrozepin, 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. Pirenzepine is a drug which is used for the treatment of peptic ulcer, gastric ulcer, and duodenal ulcer. Pirenzepine is used to treat duodenal or stomach ulcers or intestine problems. Pirenzepine is a very strong basic compound (based on its pKa). In humans, pirenzepine is involved in pirenzepine action pathway. Pirenzepine is a muscarinic receptor antagonist and binds to the muscarinic acetylcholine receptor. 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. These medications are used to relieve cramps or spasms of the stomach, intestines, and bladder. It is generally well tolerated by patients. It also potentiates the effect of other antiulcer agents such as cimetidine and ranitidine. It may also be used to prevent nausea, vomiting, and motion sickness.
Structure
Data?1582753222
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, pirenzepinMeSH
Chemical FormulaC19H21N5O2
Average Molecular Weight351.4023
Monoisotopic Molecular Weight351.169524941
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
CAS Registry Number28797-61-7
SMILES
CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1
InChI Identifier
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)
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
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.68 g/LNot Available
LogP0.6Not 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9274000000-86b6dd314412cb49103eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-0869000000-07871a195a1b07560aafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2920000000-f203c4e307f7cbb9ccbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9730000000-81e7602ee0e57b11f329Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-eba2d6236adedf16c650Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-0295000000-d2fe7d74f38b69f23111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-1960000000-11b9714bc5655d979a4fSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00670 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00670 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00670
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4682
KEGG Compound IDC07508
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPirenzepine
METLIN IDNot Available
PubChem Compound4848
PDB IDNot Available
ChEBI ID8247
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Czepita D: [Fundamentals of modern treatment of myopia]. Ann Acad Med Stetin. 2005;51(2):5-9. [PubMed:16519089 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
51420.4
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 ]