vidofludimus   Click here for help

GtoPdb Ligand ID: 9860

Synonyms: 4SC-101 | IMU-838 (vidofludimus calcium) | SC12267
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Vidofludimus (4SC-101) is a small molecule dihydroorotate dehydrogenase (DHOD) inhibitor that was developed for immunosuppressive potential [3]. It has an improved toxicity profile in comparison to the clinically used disease modifying anti-rheumatic drug (DMARD) leflunomide.
Since its initial development, vidofludimus has been superceded by IMU-838 which is an orally active polymorph of vidofludimus calcium (PubChem CID: 56944639) [5].SARS-CoV-2 and COVID-19: The target of vidofludimus, DHODH, plays a role in the metabolism of activated T cells and B cells to regulate the inflammatory response. It has been advanced to clinical trial in patients with severe COVID-19, to as attempt to block the release of pro-inflammatory cytokines and temper hyperinflammation in these patients.
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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 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 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 75.63
Molecular weight 355.12
XLogP 3.34
No. Lipinski's rules broken 0
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 COc1cccc(c1)c1ccc(c(c1)F)NC(=O)C1=C(CCC1)C(=O)O
Isomeric SMILES COc1cccc(c1)c1ccc(c(c1)F)NC(=O)C1=C(CCC1)C(=O)O
InChI InChI=1S/C20H18FNO4/c1-26-14-5-2-4-12(10-14)13-8-9-18(17(21)11-13)22-19(23)15-6-3-7-16(15)20(24)25/h2,4-5,8-11H,3,6-7H2,1H3,(H,22,23)(H,24,25)
InChI Key XPRDUGXOWVXZLL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Phase 2 clinical trials designed to determine the clinical efficacy of the original formulation, 4SC-101 in inflammatory bowel disease and rheumatoid arthritis have been completed. Published results from the IBD trial NCT00820365 are indicative of clinical efficacy in this indication [2]. Vidofludimus missed the primary endpoint in a Phase 2b RA trial. A new formulation of vidofludimus known as IMU-838 has replaced the original agent, and this is under active evaluation for clinical efficacy in ulcerative colitis, primary sclerosing cholangitis, multiple sclerosis [6] and COVID-19.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04379271 A Study to Evaluate the Efficacy, Safety and Tolerability of IMU-838 as Addition to Investigator's Choice of Standard of Care Therapy, in Patients With Coronavirus Disease 19 (COVID-19) Phase 2/Phase 3 Interventional Immunic AG
NCT03722576 Vidofludimus Calcium for Primary Sclerosing Cholangitis Phase 2 Interventional Mayo Clinic
NCT03341962 Phase 2 Dose-finding IMU-838 for Ulcerative Colitis Phase 2 Interventional Immunic AG
NCT03846219 MRI Trial to exPlore the efficAcy and Safety of IMU-838 in Relapsing Remitting Multiple Sclerosis (EMPhASIS) Phase 2 Interventional Immunic AG Immunic have informally reported that IMU-838 (vidofludimus calcium, treatment for 6 months) has significant anti-demyelination efficacy in patients with RR MS (determined by MRI as a decrease in brain lesions). This trial includes the availability of an extension phase through which patients can choose to keep receiving treatment for up to nine and a half years.