vibegron   Click here for help

GtoPdb Ligand ID: 10100

Synonyms: compound 7 [PMID: 26709102] | Gemtesa® | KRP-114V [2] | MK-4618 | MK4618
Approved drug
vibegron is an approved drug (FDA (2020), EMMA (2024))
Compound class: Synthetic organic
Comment: Vibegron (MK-4618) is a potent and selective β3 adrenoceptor agonist that was developed by Merck as a pharmacological modulator for the management of overactive bladder [2-3].
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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 6
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 96.25
Molecular weight 444.22
XLogP 2.47
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 O=C(C1CCc2n1c(=O)ccn2)Nc1ccc(cc1)CC1CCC(N1)C(c1ccccc1)O
Isomeric SMILES O=C([C@@H]1CCc2n1c(=O)ccn2)Nc1ccc(cc1)C[C@@H]1CC[C@@H](N1)[C@@H](c1ccccc1)O
InChI InChI=1S/C26H28N4O3/c31-24-14-15-27-23-13-12-22(30(23)24)26(33)29-19-8-6-17(7-9-19)16-20-10-11-21(28-20)25(32)18-4-2-1-3-5-18/h1-9,14-15,20-22,25,28,32H,10-13,16H2,(H,29,33)/t20-,21+,22-,25+/m0/s1
InChI Key DJXRIQMCROIRCZ-XOEOCAAJSA-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/)
Bioactivity Comments
Vibegron is inactive at the β1 and β2 adrenoceptors [3]. It does not inhbit the hERG channel or the drug-metabolising CYP450 isozymes 2C9, 2D6 and 3A4.
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
β3-adrenoceptor Monkey Agonist Agonist 9.2 pEC50 - 3
⤷ pEC50 9.2 (EC50 5.7x10-10 M) [3]
β3-adrenoceptor Primary target of this compound Hs Agonist Agonist 8.7 – 9.0 pEC50 - 1-3
⤷ pEC50 8.7 – 9.0 [1-3]
β3-adrenoceptor Clf Agonist Agonist 8.0 pEC50 - 3
⤷ pEC50 8.0 (EC50 1.1x10-8 M) [3]
β3-adrenoceptor Rn Agonist Agonist 7.1 pEC50 - 3
⤷ pEC50 7.1 (EC50 8.6x10-8 M) [3]