obefazimod   Click here for help

GtoPdb Ligand ID: 11698

Synonyms: ABX-464 | ABX464 | MMV1581032 | SPL-464
Compound class: Synthetic organic
Comment: We obtained the chemical structure for obefazimod from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 49846599, with the association to ABX464, a first-in-class, clinical-stage, oral small molecule immunomodulator [2]. ABX464 was originally developed for antiviral potential (associated via ChEMBL to the Medicines for Malaria Venture (MMV) compound MMV1581032), but was redeployed for chronic inflammatory diseases because of its potent anti-inflammatory effects in preclinical testing. ABX464 is reported to bind to the RNA cap-binding complex, which modulates both viral and cellular RNA biogenesis [1].
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 CDK toolkit. 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 1
Rotatable bonds 4
Topological polar surface area 34.15
Molecular weight 338.04
XLogP 5.85
No. Lipinski's rules broken 1
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.

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Canonical SMILES Clc1cccc2c1nc(cc2)Nc1ccc(cc1)OC(F)(F)F
Isomeric SMILES Clc1cccc2ccc(nc12)Nc1ccc(cc1)OC(F)(F)F
InChI InChI=1S/C16H10ClF3N2O/c17-13-3-1-2-10-4-9-14(22-15(10)13)21-11-5-7-12(8-6-11)23-16(18,19)20/h1-9H,(H,21,22)
InChI Key OZOGDCZJYVSUBR-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
ABX464 has been advanced to clinical evaluation in inflammatory diseases (IBDs and rheumatoid arthritis) and viral infections (HIV, SARS-CoV-2).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04393038 ABX464 in Treating Inflammation and Preventing Acute Respiratory Failure in Patients With COVID-19 Phase 2/Phase 3 Interventional Abivax S.A. ABX464 was entered into this clinical trial to evaluate its anti-inflammatory otential in COVID-19 patients. The study was terminated following interim analysis which concluded that continuing was futile.
NCT03813199 Study of Two Doses of ABX464 in Participants With Moderate to Severe Rheumatoid Arthritis Phase 2 Interventional Abivax S.A.
NCT03760003 Dose-Ranging Phase 2b Study of ABX464 in Moderate to Severe Ulcerative Colitis Phase 2 Interventional Abivax S.A.
NCT02735863 ABX464 in Fully Controlled HIV Infected Patients Treated With Boosted Protease Inhibitor Treatment Phase 2 Interventional Abivax S.A.
NCT03368118 Study Evaluating the Long-term Safety and Efficacy of ABX464 in Active Ulcerative Colitis Phase 2 Interventional Abivax S.A. 3
NCT03093259 ABX464 in Subjects With Moderate to Severe Active Ulcerative Colitis Phase 2 Interventional Abivax S.A. 3