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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 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. It is in a class of drugs known as muscarinic receptor antagonists - acetylcholine being the neurotransmitter of the parasympathetic nervous system which initiates the rest-and-digest state (as opposed to fight-or-flight), resulting in an increase in gastric motility and digestion; whereas pirenzepine would inhibit these actions and cause decreased gastric motility leading to delayed gastric emptying and constipation. Pirenzepine is a very strong basic compound (based on its pKa). In humans, pirenzepine is involved in pirenzepine action pathway. Pirenzepine has been investigated for use in myopia control. Pirenzepine (Gastrozepin), an M1 selective antagonist, is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm. It promotes the homodimerization or oligomerisation of M1 receptors. It has no effects on the brain and spinal cord as it cannot diffuse through the blood–brain barrier.
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, pirenzepinHMDB
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.68 g/LNot Available
LogP0.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available181.172http://allccs.zhulab.cn/database/detail?ID=AllCCS00000921
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.34331661259
DarkChem[M-H]-180.06931661259
DeepCCS[M+H]+186.48430932474
DeepCCS[M-H]-184.12630932474
DeepCCS[M-2H]-218.42930932474
DeepCCS[M+Na]+193.78130932474
AllCCS[M+H]+183.032859911
AllCCS[M+H-H2O]+180.032859911
AllCCS[M+NH4]+185.832859911
AllCCS[M+Na]+186.632859911
AllCCS[M-H]-184.432859911
AllCCS[M+Na-2H]-184.132859911
AllCCS[M+HCOO]-183.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PirenzepineCN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC14076.7Standard polar33892256
PirenzepineCN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC12972.4Standard non polar33892256
PirenzepineCN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC13077.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pirenzepine,1TMS,isomer #1CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C)C3=CC=CN=C32)CC12846.4Semi standard non polar33892256
Pirenzepine,1TMS,isomer #1CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C)C3=CC=CN=C32)CC12924.1Standard non polar33892256
Pirenzepine,1TMS,isomer #1CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C)C3=CC=CN=C32)CC14326.0Standard polar33892256
Pirenzepine,1TBDMS,isomer #1CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=CN=C32)CC13033.5Semi standard non polar33892256
Pirenzepine,1TBDMS,isomer #1CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=CN=C32)CC13129.6Standard non polar33892256
Pirenzepine,1TBDMS,isomer #1CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=CN=C32)CC14385.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pirenzepine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9274000000-86b6dd314412cb49103e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pirenzepine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pirenzepine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 10V, Positive-QTOFsplash10-0ik9-0869000000-07871a195a1b07560aaf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 20V, Positive-QTOFsplash10-03di-2920000000-f203c4e307f7cbb9ccba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 40V, Positive-QTOFsplash10-01ox-9730000000-81e7602ee0e57b11f3292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 10V, Negative-QTOFsplash10-0udi-0039000000-eba2d6236adedf16c6502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 20V, Negative-QTOFsplash10-0ik9-0295000000-d2fe7d74f38b69f231112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 40V, Negative-QTOFsplash10-03xr-1960000000-11b9714bc5655d979a4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 10V, Positive-QTOFsplash10-0udi-0209000000-abe020ee7c3bd795b2602021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 20V, Positive-QTOFsplash10-0w29-1429000000-17de4fa81cf69470057b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 40V, Positive-QTOFsplash10-03kc-9230000000-b37f79f5ccdc399c3a222021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 10V, Negative-QTOFsplash10-0udi-0029000000-6d0cde8b33849d6a8df72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 20V, Negative-QTOFsplash10-0w29-0059000000-c5eade40c8f67c093c192021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pirenzepine 40V, Negative-QTOFsplash10-0bt9-0090000000-ca4cb52f06eeaadb07542021-10-11Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents 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 ]