lenabasum   Click here for help

GtoPdb Ligand ID: 9772

Synonyms: ajulemic acid | CPL-7075 | CPL7075 | CT-3 | IP-751 | IP751
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Lenabasum (ajulemic acid) is a synthetic derivative of the non-psychoactive cannabinoid THC metabolite 11-nor-9-Carboxy-THC (PubChem CID 108207) [10]. It is a non-selective cannabinoid receptor agonist [5,7]. Lenabasum exhibits potentially useful analgesic and anti-inflammatory actions [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
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 2
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 66.76
Molecular weight 400.26
XLogP 6.96
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 CCCCCCC(c1cc(O)c2c(c1)OC(C1C2CC(=CC1)C(=O)O)(C)C)(C)C
Isomeric SMILES CCCCCCC(c1cc(O)c2c(c1)OC([C@H]1[C@H]2CC(=CC1)C(=O)O)(C)C)(C)C
InChI InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1
InChI Key YCHYFHOSGQABSW-RTBURBONSA-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
Ajulemic acid (research code JBT-101) is being evaluated as a treatment for systemic lupus erythematosus (SLE) in Phase 2 clinical trial NCT03093402.
It was also more effective in reducing chronic neuropathic pain than placebo in a Phase 2 clinical trial [6].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03093402 JBT-101 in Systemic Lupus Erythematosus (SLE) Phase 2 Interventional National Institute of Allergy and Infectious Diseases (NIAID)
NCT02466243 Safety, Tolerability, and Efficacy of JBT-101 in Subjects With Dermatomyositis Phase 2 Interventional Corbus Pharmaceuticals Inc. Primary completion of this trial is expected in September 2021, with full completion a year later. Data is likely to be shared by the end of 2021.
NCT03398837 Trial to Evaluate Efficacy and Safety of Lenabasum in Diffuse Cutaneous Systemic Sclerosis Phase 3 Interventional Corbus Pharmaceuticals Inc. Failure of lenabasum in this Phase 3 study in cutaneous systemic sclerosis patients was advised in September 2020.
NCT02465437 Safety, Tolerability, Efficacy, and Pharmacokinetics of JBT-101 in Systemic Sclerosis Phase 2 Interventional Corbus Pharmaceuticals Inc. 8
NCT02465450 Safety, Tolerability, Pharmacokinetics, and Efficacy of JBT-101 (Lenabasum) in Cystic Fibrosis Phase 2 Interventional Corbus Pharmaceuticals Inc. Despite positive indications from this study lenabasum failed to do better than placebo at reducing pulmonary exacerbations in Phase 2b cystic fibrosis trial NCT03451045. Development in CF was subsequently discontinued. 4