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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Click here for structure editor
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/)
References
1. Crater GD, Lalonde K, Ravenelle F, Harvey M, Després JP. (2024)
Effects of CB1R inverse agonist, INV-202, in patients with features of metabolic syndrome. A randomized, placebo-controlled, double-blind phase 1b study.
Diabetes Obes Metab, 26 (2): 642-649. [PMID:37941317]
2. Ghosh A, Peyot ML, Leung YH, Ravenelle F, Madiraju SRM, Prentki M. (2023)
A peripherally restricted cannabinoid-1 receptor inverse agonist promotes insulin secretion and protects from cytokine toxicity in human pancreatic islets.
Eur J Pharmacol, 944: 175589. [PMID:36773683]
3. Jacquot L, Pointeau O, Roger-Villeboeuf C, Passilly-Degrace P, Belkaid R, Regazzoni I, Leemput J, Buch C, Demizieux L, Vergès B et al.. (2023)
Therapeutic potential of a novel peripherally restricted CB1R inverse agonist on the progression of diabetic nephropathy.
Front Nephrol, 3: 1138416. [PMID:37675364]
4. Kumari P, Dvorácskó S, Enos MD, Ramesh K, Lim D, Hassan SA, Kunos G, Cinar R, Iyer MR, Rosenbaum DM. (2024)
Structural mechanism of CB1R binding to peripheral and biased inverse agonists.
Nat Commun, 15 (1): 10694. [PMID:39695122]
5. Liu Z, Iyer MR, Godlewski G, Jourdan T, Liu J, Coffey NJ, Zawatsky CN, Puhl HL, Wess J, Meister J et al.. (2021)
Functional Selectivity of a Biased Cannabinoid-1 Receptor (CB1R) Antagonist.
ACS Pharmacol Transl Sci, 4 (3): 1175-1187. [PMID:34151207]
6. Novo Nordisk. 
Novo Nordisk Company announcement; Financial report for the period 1 January 2024 to 31 December 2024.
Accessed on 06/02/2025. Modified on 06/02/2025. www.novonordisk.com, https://www.novonordisk.com/content/nncorp/global/en/news-and-media/news-and-ir-materials/news-details.html?id=915255