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monlunabant   Click here for help

GtoPdb Ligand ID: 13717

Synonyms: (S)-MRI-1891 | INV-202 | MRI-1891
PDB Ligand
Compound class: Synthetic organic
Comment: Monlunabant (INV-202; MRI-1891) is a peripherally acting cannabinoid CB1 receptor inverse agonist [2,4-5]. Structurally it is a derivative of ibipinabant that has been modified to prevent the molecule from penetrating the blood-brain barrier. Bias towards β-arrestin-2 recruitment over G protein signalling has been claimed [5].
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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
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 9
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 137.96
Molecular weight 591.01
XLogP 2.3
No. Lipinski's rules broken 1

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 CC(=O)N/C(=N/C(=N/S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)/N2C[C@H](C3=CC=CC=C3)C(=N2)C4=CC=C(C=C4)Cl)/N
Isomeric SMILES CC(=O)N/C(=N/C(=N/S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)/N2C[C@@H](C(=N2)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)/N
InChI InChI=1S/C26H22ClF3N6O3S/c1-16(37)32-24(31)33-25(35-40(38,39)21-13-9-19(10-14-21)26(28,29)30)36-15-22(17-5-3-2-4-6-17)23(34-36)18-7-11-20(27)12-8-18/h2-14,22H,15H2,1H3,(H3,31,32,33,35,37)/t22-/m1/s1
InChI Key GYJPQNPVIJXXTA-JOCHJYFZSA-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/)
No information available.
Summary of Clinical Use Click here for help
Monlunabant was proposed for weight loss potential (targeting metabolic syndrome and obesity) and diabetic kidney disease (nephropathy) [3]. Satisfactory tolerability, weight loss and improvements in metabolic syndrome markers have been reported from a phase 1 study in patients with features of metabolic syndrome [1]. Mild to moderate neuropsychiatric side effects were detected in a phase 2 diabetic kidney disease trial, and development of this candidate was discontinued.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT06542536 A Research Study Investigating Safety and Concentration in the Blood After One Dose Tablet of the New Medicine Monlunabant in Healthy Weight Japanese and Caucasian Men Phase 1 Interventional Novo Nordisk A/S
NCT05514548 Phase 2 Study of INV-202 in Patients With Diabetic Kidney Disease Phase 2 Interventional Inversago Pharma Inc.
NCT05891834 Study of INV-202 in Patients With Obesity and Metabolic Syndrome Phase 2 Interventional Inversago Pharma Inc.
NCT05282446 A Study to Explore the PK and PD of INV-202 in Metabolic Syndrome Phase 1 Interventional Inversago Pharma Inc. 1