You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-10-23 19:06:23 UTC
HMDB IDHMDB0014808
Secondary Accession Numbers
  • HMDB14808
Metabolite Identification
Common NamePirenzepine
DescriptionAn 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
ValueSource
11-((4-Methyl-1-piperazinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneChEBI
PirenzepinaChEBI
PirenzepinumChEBI
Dihydrochloride, pirenzepineMeSH
UlcoprotectMeSH
Dolorgiet brand OF pirenzepine dihydrochlorideMeSH
GastrozepinMeSH
Piren basanMeSH
Piren-basanMeSH
Pirenzepin ratiopharmMeSH
Pirenzepin-ratiopharmMeSH
Pirenzepine dihydrochlorideMeSH
GastrotsepinMeSH
PirenzepinMeSH
UlgescumMeSH
CT-Arzneimittel brand OF pirenzepine dihydrochlorideMeSH
Pirenzepin von CTMeSH
Ratiopharm brand OF pirenzepine dihydrochlorideMeSH
Azupharma brand OF pirenzepine dihydrochlorideMeSH
Boehringer ingelheim brand OF pirenzepine dihydrochlorideMeSH
L-S 519MeSH
PyrenzepineMeSH
Sagitta brand OF pirenzepine dihydrochlorideMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzodiazepines
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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9274000000-86b6dd314412cb49103eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-0869000000-07871a195a1b07560aafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2920000000-f203c4e307f7cbb9ccbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9730000000-81e7602ee0e57b11f329View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-eba2d6236adedf16c650View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-0295000000-d2fe7d74f38b69f23111View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-1960000000-11b9714bc5655d979a4fView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Pirenzepine PathwayPw000324Pw000324 greyscalePw000324 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00670 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00670 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00670
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]