pirenzepine   Click here for help

GtoPdb Ligand ID: 328

Approved drug
pirenzepine is an approved drug
Compound class: Synthetic organic
Comment: Pirenzepine muscarinic acetylcholine receptor antagonist, selective for the M1 receptor subtype.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 74.23
Molecular weight 351.17
XLogP 1.32
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
Isomeric SMILES CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
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)
InChI Key RMHMFHUVIITRHF-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
International Nonproprietary Names Click here for help
INN number INN
3476 pirenzepine
Database Links Click here for help
Specialist databases
GPCRdb Ligand pirenzepine
Other databases
BindingDB Ligand 50005675
BitterDB Ligand 676
CAS Registry No. 28797-61-7 (source: Scifinder)
ChEMBL Ligand CHEMBL9967
DrugCentral Ligand 2200
GtoPdb PubChem SID 135650832
PubChem CID 4848
Search Google for chemical match using the InChIKey RMHMFHUVIITRHF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RMHMFHUVIITRHF
Search PubMed clinical trials pirenzepine
Search PubMed titles pirenzepine
Search PubMed titles/abstracts pirenzepine
UniChem Compound Search for chemical match using the InChIKey RMHMFHUVIITRHF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RMHMFHUVIITRHF-UHFFFAOYSA-N
Wikipedia Pirenzepine

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MedChemExpress
Pirenzepine (links to external site)
Cat. No. HY-17037A